Proxy Statement (Form DEF 14A)

DULUTH HOLDINGS INC.

201 East Front Street

Mount Horeb, Wisconsin 53572

NOTICE OF ANNUAL MEETING OF SHAREHOLDERS

June 3, 2026

To the Shareholders of Duluth Holdings Inc.:

The 2026 Annual Meeting of Shareholders of Duluth Holdings Inc. will be held in person at the headquarters of Duluth Holdings Inc., 201 East Front Street, Mount Horeb, Wisconsin 53572, on June 3, 2026 at 8:30 a.m., Central Time, for the following purposes:

Shareholders of record at the close of business on March 27, 2026 are entitled to notice of and to vote at the annual meeting and at all adjournments of the annual meeting.

Holders of a majority of the votes entitled to be cast must be present in person or by proxy in order for the annual meeting to be held. As allowed under the Securities and Exchange Commission's rules, we have elected to furnish our proxy materials over the Internet. Accordingly, we have mailed to our shareholders of record and beneficial owners a Notice of Internet Availability of Proxy Materials (the "Notice") containing instructions on how to access the attached proxy statement and our annual report to shareholders via the Internet and how to vote online.

Whether or not you expect to attend the annual meeting in person, you are urged to vote by voting electronically via the Internet, by a telephone vote or, as applicable, by completing and mailing the proxy card. Instructions for electronic voting via the Internet and telephonic voting are contained in the Notice, or, as applicable, on the proxy card. If you attend the meeting and wish to vote your shares personally, you may do so by revoking your proxy at any time prior to the voting thereof. In addition, you may revoke your proxy at any time before it is voted by advising the Corporate Secretary of Duluth Holdings Inc. in writing (including by submitting a duly executed proxy bearing a later date or voting via the Internet) or by telephone of such revocation.

Important Notice Regarding the Availability of Proxy Materials for the Annual Meeting of Shareholders to be held on June 3, 2026: The annual report to shareholders and proxy statement of Duluth Holdings Inc. are available for review at www.envisionreports.com/DLTH. Instructions on how to access and review the materials on the Internet can be found on the Notice and the proxy card.

Wenyu Blanchard

Corporate Secretary

Mount Horeb, Wisconsin

April 21, 2026

DULUTH HOLDINGS INC.

201 East Front Street

Mount Horeb, Wisconsin 53572

April 21, 2026

PROXY STATEMENT

Unless the context requires otherwise, all references to "Duluth Trading," the "Company," "we," "us" or "our" refer to Duluth Holdings Inc.

The enclosed proxy is solicited by the Board of Directors of Duluth Holdings Inc. for use at the 2026 annual meeting of shareholders to be held at 8:30 a.m., Central Time, on June 3, 2026 or at any postponement or adjournment of the annual meeting, for the purposes set forth in this proxy statement and in the accompanying notice of annual meeting of shareholders. The annual meeting will be held in person at the headquarters of Duluth Trading, 201 East Front Street, Mount Horeb, Wisconsin 53572.

Under rules adopted by the Securities and Exchange Commission (the "SEC"), Duluth Trading is making this proxy statement and other annual meeting materials available on the Internet instead of mailing a printed copy of these materials to each shareholder. Shareholders who received a Notice of Internet Availability of Proxy Materials (the "Notice") by mail will not receive a printed copy of these materials other than as described below. Instead, the Notice contains instructions as to how shareholders may access and review all of the important information contained in the materials on the Internet, including how shareholders may submit proxies by telephone or over the Internet.

If you received the Notice by mail and would prefer to receive a printed copy of Duluth Trading's proxy materials, please follow the instructions for requesting printed copies included in the Notice.

The proxy statement and form of proxy are being made available to shareholders commencing on or about April 21, 2026.

The expense of this solicitation will be paid by us. No solicitation other than by mail and via the Internet is contemplated, except that our officers or employees may solicit the return of proxies from certain shareholders by telephone.

Only shareholders of record at the close of business on March 27, 2026 are entitled to notice of and to vote the shares of our Class A common stock, no par value, and Class B common stock, no par value, registered in their name at the annual meeting. As of the record date, we had outstanding 3,364,200 shares of Class A common stock and 34,764,498 shares of Class B common stock. The presence, in person or by proxy, of a majority of the votes entitled to be cast will constitute a quorum at the annual meeting. Abstentions, votes that are withheld and broker non-votes, which are proxies from brokers or nominees indicating that such persons have not received instructions from the beneficial owners or other persons entitled to vote shares, will be treated as present for purposes of determining the quorum. Each share of Class A common stock is entitled to ten votes per share, and each share of Class B common stock is entitled to one vote per share on each matter to be voted upon at the annual meeting. Shares of Class A common stock and Class B common stock vote together as a single class for each of the proposals listed below.

With respect to the proposal to elect the individuals nominated by our Board of Directors to serve as directors until the 2027 annual meeting of shareholders, votes may be cast in favor or withheld for each nominee. Votes that are withheld and broker non-votes will have no effect on the outcome of the election. With respect to the proposal to approve, by advisory vote, the compensation of our named executive officers, abstentions and broker non-votes will not be counted as votes cast, so abstentions and broker non-votes will have no effect on

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the outcome. Because this shareholder vote is advisory, it will not be binding upon the Board of Directors. However, the Compensation Committee will take into account the outcome of the vote when considering future executive compensation arrangements. With respect to the proposal to ratify the appointment of KPMG LLP as our independent registered public accountants for fiscal 2026, abstentions and broker non-votes will not be counted as voting on the proposal, so abstentions and broker non-votes will have no effect on the outcome.

If a proxy is properly submitted to us and not revoked, it will be voted in accordance with the instructions contained in the proxy. Each shareholder may revoke a previously granted proxy at any time before it is exercised by advising the Corporate Secretary of the Company in writing (including by submitting a duly executed proxy bearing a later date or voting via the Internet) or by telephone of such revocation. Attendance at the annual meeting will not, in itself, constitute revocation of a proxy. Unless otherwise directed, all proxies will be voted FOR the election of each of the individuals nominated by our Board of Directors to serve as directors until the 2027 annual meeting of shareholders, will be voted FOR approval of the compensation of our named executive officers, and will be voted FOR the appointment of KPMG LLP as our independent registered public accountants for fiscal 2026.

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CORPORATE GOVERNANCE DOCUMENTS

Certain documents relating to corporate governance matters are available in print by writing to Corporate Secretary, Duluth Holdings Inc., 201 East Front Street, Mount Horeb, Wisconsin 53572 and on the Company's website at ir.duluthtrading.com under the "Corporate Governance-Documents & Charters" tab. These documents include the following:

Information contained on the Company's website is not deemed to be a part of this proxy statement.

PROPOSAL ONE: ELECTION OF DIRECTORS

Our Board of Directors currently consists of eight directors. The term of office of each of the directors expires at the 2026 annual meeting.

Our Board of Directors proposes that the nominees described below be elected as directors for a new term ending at the 2027 annual meeting of shareholders and until their successors are duly elected, except as otherwise provided in the Wisconsin Business Corporation Law. All of the nominees are standing for re-election.

The Board of Directors has determined that a majority of the current directors are independent as defined for companies trading on The NASDAQ Stock Market LLC ("NASDAQ"). The independent directors serving on our Board of Directors as of the date of this proxy statement include Mr. David C. Finch, Ms. Janet H. Kennedy, Mr. Brett L. Paschke, Ms. Susan J. Riley, Mr. Ronald Robinson, and Mr. Scott K. Williams.

In accordance with our amended and restated articles of incorporation and amended and restated bylaws, a nominee will be elected as a director by a plurality of the votes cast in the election of directors. A plurality means that the eight persons receiving the highest number of affirmative FOR votes at the meeting will be elected. Votes that are withheld and broker non-votes will have no impact on the election. In the event that a vacancy remains, the Board of Directors may fill such vacancy at a later date or reduce the size of the Board of Directors, subject to the procedures specified in the amended and restated articles of incorporation or amended and restated bylaws. Each of the nominees has indicated a willingness to serve as a director, but if any of the nominees should decline or be unable to act as a director, the persons named in the proxy will vote for the election of another person or persons as the Board of Directors recommends.

The descriptions in this section provide certain biographical information about each of the nominees for election as a director, followed by a statement regarding the specific experience, qualifications, attributes or skills that led to the Board of Director's conclusion that each director should serve as a director of Duluth Trading.

The Board of Directors unanimously recommends that shareholders vote FOR the election of each of the nominees set forth below to serve as directors until the 2027 annual meeting, and your proxy will be so voted unless you specify otherwise.

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NOMINEES FOR DIRECTOR

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Board of Directors

Each incumbent director standing for election at the 2026 Annual Meeting of Shareholders attended at least 75% of the board meetings and meetings of committees on which such director served that were held in fiscal 2025 while such director served on the Board of Directors or the committees. The Board of Directors held twelve meetings during fiscal 2025. While the Company does not have a policy requiring board members' attendance at the annual meeting of shareholders, each director is strongly encouraged to attend our annual meeting of shareholders. All of the then current directors attended our 2025 annual meeting.

As part of its corporate governance guidelines, the Board of Directors has established a general retirement age of 77, where no individual will be nominated for election to the Board of Directors after his or her 77th birthday. The Board of Directors may, at its discretion, waive the age limitation in special circumstances. While Mr. S. Schlecht was 78 at the time he was nominated for election, we amended his employment agreement to extend the term of his agreement for two years and nominated him to stand for election at the 2026 annual meeting.

Any interested party who wishes to communicate directly with the Board of Directors, any of its committees, an independent director or with the independent directors as a group may do so by writing to the Corporate Secretary of the Company at 201 East Front Street, Mount Horeb, Wisconsin 53572 or by calling (608) 424-1544. The Corporate Secretary will forward a summary of all communications to the Board of Directors, that committee, that independent director or the independent directors as a group, as applicable.

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Controlled Company

Because Mr. S. Schlecht controls a majority of our outstanding voting power, we are a "controlled company" under the corporate governance rules of NASDAQ. Therefore, we are not required to have a majority of our Board of Directors be independent, nor are we required to have a compensation committee or an independent nominating function. While our Board of Directors has determined to have both a compensation committee and nominating and governance committee, Mr. S. Schlecht currently serves as a member of both committees.

Board of Directors Composition

Our amended and restated bylaws provide that the size of our Board of Directors will be determined from time to time by a majority of the then authorized number of directors, but in no case may be less than one director. The Board of Directors currently consists of eight directors, six of whom qualify as independent directors under the rules and regulations of the SEC and the NASDAQ Listing Rules.

Independence of our Board of Directors and Committees

The rules of NASDAQ generally require that a majority of the members of a listed company's board of directors be independent. In addition, the listing rules generally require that, subject to specified exceptions, each member of a listed company's audit, compensation and governance committees be independent. Although we are a "controlled company" under the corporate governance rules of NASDAQ and, therefore, are not required to comply with certain rules requiring director independence, we have nevertheless opted to have a majority of the members of our Board of Directors be independent.

Accordingly, our Board of Directors has evaluated the independence of its members based upon the rules of the NASDAQ Stock Market and the SEC and the transactions referenced under "Certain Relationships and Related Party Transactions." Applying these standards, our Board of Directors determined that none of the directors who currently serve or who will stand for election at the 2026 annual meeting, other than Mr. S. Schlecht and Ms. Pugliese, have a relationship that would interfere with the exercise of independent judgment in carrying out the responsibilities of a director and that each of those directors is "independent" as that term is defined under Rule 5605(a)(2) of the NASDAQ Listing Rules. Mr. S. Schlecht is not considered independent because Mr. S. Schlecht was previously employed as Chief Executive Officer and Executive Chairman of the Company and is currently employed in the capacity of Senior Advisor. Ms. Pugliese is not considered independent because she serves as our President and Chief Executive Officer. Our Board of Directors also determined that each non-employee director who serves as a member of the Audit, Compensation, and Nominating and Governance Committees satisfies the independence standards for such committee established by the SEC and the NASDAQ Listing Rules, as applicable.

Board of Directors Leadership Structure

The Board of Directors has not adopted a formal policy regarding the separation of the roles of chair of the board and chief executive officer because the Board of Directors believes that it is in our best interests to make that determination from time to time based on the position and direction of our organization and the composition of our Board of Directors. As of the date of this proxy statement, the positions of the chair of the board and the chief executive officer are separated and the individuals serving in those positions remain actively involved in our business. We believe this is appropriate because the Board of Directors includes a number of seasoned independent directors. In concluding that having Mr. S. Schlecht serve as Chairman and Ms. Pugliese serve as Chief Executive Officer represents the appropriate structure for us at this time, our Board of Directors considered the benefits of having the Chairman serve as a bridge between management and our Board of Directors, ensuring that both groups act with a common purpose. Our Board of Directors also considered Mr. S. Schlecht's knowledge regarding our operations and the industry in which we compete and his ability to promote communication, to synchronize activities between our Board of Directors and our senior management and to provide leadership to the Board of Directors in coordinating our strategic objectives.

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Our Board of Directors also recognizes that depending on the circumstances, other leadership models, such as combining the roles of chair of the board and chief executive officer as we have in the past, may again be appropriate. Accordingly, our Board of Directors may periodically review its leadership structure.

Committees of the Board of Directors

The Board of Directors has standing Audit, Compensation, and Nominating and Governance Committees, each of which is governed in accordance with a written charter. These charters are available on the Company's website at ir.duluthtrading.com under the "Corporate Governance-Documents & Charters" tab. Members of the Board of Directors serve on these committees until their resignation or until otherwise determined by our Board of Directors.

Audit Committee

The current members of the Audit Committee are Mr. Finch, Ms. Kennedy, Mr. Paschke and Ms. Riley. Mr. Finch, Ms. Kennedy, Mr. Paschke and Ms. Riley satisfy the heightened audit committee independence requirements under the NASDAQ Listing Rules and Rule 10A-3 of the Exchange Act.

Ms. Riley serves as the chair of our Audit Committee and has been designated as our "audit committee financial expert," as that term is defined under SEC rules implementing Section 407 of the Sarbanes-Oxley Act, and possesses the requisite financial sophistication, as defined under the applicable rules and regulations of NASDAQ. The Audit Committee operates under a written charter.

Under its charter, our Audit Committee is responsible for, among other things:

The Audit Committee held five meetings during fiscal 2025.

Compensation Committee

The current members of the Compensation Committee are Mr. Robinson, Mr. S. Schlecht and Mr. Williams. Mr. Williams serves as the chair of our Compensation Committee. Mr. Robinson and Mr. Williams are non-employee directors within the meaning of Rule 16b-3 of the rules promulgated under the Exchange Act, and are independent directors as defined by the NASDAQ Listing Rules.

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Under its charter, our Compensation Committee is responsible for, among other things:

The Compensation Committee may delegate authority with respect to any of its functions to officers of the Company, committees comprised of such persons, or a subcommittee of the Committee, including a subcommittee consisting of at least two members, each of whom qualifies as a "non-employee director" within the meaning of Rule 16b-3 of the rules promulgated under the Exchange Act.

The Compensation Committee held five meetings during fiscal 2025.

Generally, our Chief Executive Officer makes recommendations as to the amount or form of compensation for senior management, including any salary adjustments, cash incentive awards or equity-based awards, which are then evaluated and determined by the Compensation Committee. For fiscal 2025, the Compensation Committee approved "executive officer"-related compensation and the Board of Directors ratified the compensation related to each of Ms. Pugliese and Mr. Sato, as President and Chief Executive Officer and to Mr. S. Schlecht as Chairman and Senior Advisor. The Compensation Committee has engaged the services of Meridian Compensation Partners, LLC ("Meridian") to provide advice from time to time on executive officer and non-employee director compensation and matters related to the Company's compensation practices. The Compensation Committee has evaluated the independence of Meridian pursuant to SEC and NASDAQ rules and no relationships were identified that would impact Meridian's independence or present a conflict of interest.

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Nominating and Governance Committee

The current members of the Nominating and Governance Committee are Mr. Finch, Mr. Paschke, Mr. S. Schlecht and Mr. Williams. Mr. Finch serves as the chair of our Nominating and Governance Committee. Mr. Finch, Mr. Paschke and Mr. Williams are independent directors as defined by the NASDAQ Listing Rules. Under its charter, our Nominating and Governance Committee is responsible for, among other things:

When reviewing the qualifications of proposed Board of Directors nominees, including candidates nominated by shareholders in accordance with our bylaws, the Nominating and Governance Committee considers whether each candidate would qualify as independent under the applicable NASDAQ Listing Rules, and where appropriate, his or her financial expertise, and any other qualifications the Nominating and Governance Committee deems relevant, which may include, without limitation, experience in different substantive areas such as retail operations, marketing, technology, distribution, and finance.

The Nominating and Governance Committee held four meetings during fiscal 2025.

Board of Directors Oversight of Risk

The Board of Directors is actively involved in oversight of risks that could affect us. This oversight is conducted in part through committees of the Board of Directors, but the full Board of Directors has retained responsibility for general oversight of risks. The Board of Directors intends to satisfy this responsibility through full reports by each committee regarding its considerations and actions, regular reports directly from officers responsible for oversight of particular risks within the Company as well as through internal and external audits.

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COMPENSATION COMMITTEE INTERLOCKS AND INSIDER PARTICIPATION

None of our executive officers currently serves, or has served during the last year, as a member of the board of directors or compensation committee of any entity that has one or more executive officers serving on our Board of Directors or Compensation Committee.

Mr. S. Schlecht served as a member of our Compensation Committee during fiscal 2025. For a discussion of relationships requiring disclosure under Item 404 of Regulation S-K, see "Certain Relationships and Related Party Transactions."

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CERTAIN RELATIONSHIPS AND RELATED PARTY TRANSACTIONS

The following is a description of transactions, since January 28, 2024, to which we have been a party or will be a party, in which the amount involved exceeded or will exceed $120,000, and in which any of our executive officers or directors, or an affiliate or immediate family member thereof, or 5% shareholder of any class of our common stock, had or will have a direct or indirect material interest.

Leasing Arrangements

Effective April 3, 2019, we entered into a lease with Schlecht Retail Ventures LLC, the sole members of which are Mr. and Mrs. S. Schlecht, for our photo studio located at 119 S. 2nd Street, Mt. Horeb, Wisconsin. The lease provides for a base monthly rent of $4,083 with a 2% increase each year. The initial term of the lease was for five years and began on June 1, 2019. We extended the lease term for an additional five years on June 1, 2024. We have the option to extend the term for one additional period of five years thereafter.

We leased a 7,710 square foot building and the surrounding land for our flagship store located at 100 West Main Street, Mt. Horeb, Wisconsin (the "Flagship Lease"), from Schlecht Retail Ventures LLC. The Flagship Lease began February 14, 2010 and was scheduled to expire on February 28, 2025. Effective January 17, 2017, we terminated our Flagship Lease and entered into a new lease for the same 7,710 square foot building, along with the surrounding land located at 100 West Main Street, Mt. Horeb, Wisconsin and an additional 5,416 square foot building in order to expand our square footage of our flagship store at 102 West Main Street, Mt. Horeb, Wisconsin (the "Current Flagship Lease"). The Current Flagship Lease began on February 1, 2017 and expires on January 31, 2027, with multiple options to renew thereafter. The Current Flagship Lease provides for initial monthly rent payments of $12,000 in years one through three, rent payments of $12,600 in years four through seven, and monthly rent payments of $13,104 in years eight through ten.

The aggregate amount of all periodic payments due under the leases described above after our fiscal year ended February 1, 2026 are as follows:

Other Transactions

Richard W. Schlecht, the son of Mr. S. Schlecht, receives compensation in his capacity as Senior Vice President of Product Development and Sourcing. Richard W. Schlecht received compensation of $502,458 in fiscal 2024, $554,170 in fiscal 2025 and approximately $327,332 for fiscal 2026 through the filing of this proxy statement.

Since January 28, 2024, there have been no other transactions (other than otherwise noted herein) and there are no currently proposed transactions in which we were or are to be a participant and the amount involved exceeds $120,000, and in which any of our executive officers or directors had or will have a direct or indirect material interest.

Policies and Procedures for Related-Party Transactions

Our Board of Directors adopted a written related party transaction policy regarding transactions with related persons. This policy requires that a "related person" (as defined in paragraph (a) of Item 404 of Regulation S-K) promptly disclose to our chief financial officer any "related party transaction" (defined as any transaction that

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we anticipate would be reportable by us under Item 404(a) of Regulation S-K in which we were or are to be a participant, the amount involved exceeds $120,000 and a related person had or will have a direct or indirect material interest) and all material facts with respect thereto. The chief financial officer will then promptly communicate that information to our Audit Committee. No related party transaction will be executed without the approval or ratification of our Audit Committee or our Board of Directors. It is our policy that directors interested in a related party transaction will recuse themselves from any vote on a related party transaction in which they have an interest. The policy also contains standing authorizations for certain transactions previously disclosed in the Company's filings with the SEC.

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PROPOSAL TWO: ADVISORY VOTE ON APPROVAL OF THE COMPENSATION OF NAMED EXECUTIVE OFFICERS

Under the Dodd-Frank Wall Street Reform and Consumer Protection Act (the "Dodd-Frank Act") and Section 14A of the Securities Exchange Act of 1934, as amended ("Section 14A"), our shareholders are entitled to vote to approve, by an advisory vote, the compensation of our named executive officers, as disclosed in this proxy statement. Accordingly, we are asking shareholders to approve the following nonbinding resolution regarding the compensation of our named executive officers as disclosed in this proxy statement:

RESOLVED, that the Company's shareholders approve, on an advisory basis, the compensation paid to our named executive officers, as disclosed in this proxy statement pursuant to Item 402 of Regulation S-K.

This vote is often referred to as a "say-on-pay" vote. As an advisory vote, the "say-on-pay" vote is not binding on the Company, the Board of Directors, or the Compensation Committee. However, the Board of Directors values the opinions expressed by our shareholders, and the Board of Directors and the Compensation Committee intend to consider the results of this vote in making determinations in the future regarding executive compensation policies and practices in response to these results.

For example, the Company held a say-on-pay vote at its 2025 annual meeting of shareholders to approve the compensation of its named executive officers. This shareholder resolution was approved by approximately 98% of the votes cast. The Board of Directors and the Compensation Committee have considered the results of this vote in making determinations regarding the executive compensation policies and practices described in the proxy statement.

Approval of the compensation of the Company's named executive officers requires that the number of votes cast in favor of the proposal exceeds the number of votes cast against it. Abstentions and broker non-votes will not be counted as votes cast and, therefore, will have no impact on the approval of the proposal.

The Board of Directors unanimously recommends that you vote FOR approval of the compensation of the Company's named executive officers as described in this proxy statement, and your proxy will be so voted unless you specify otherwise.

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EXECUTIVE COMPENSATION

Overview

This section provides compensation information about the following individuals:

In the discussion below, we refer to this group of executives as the "named executive officers" or "NEOs," which includes the "executive officers" for whom disclosure is required under the applicable rules of the SEC. The remainder of this section provides a general summary of our compensation policies and practices and discusses the aggregate compensation we paid to our named executive officers in fiscal 2024 and fiscal 2025. As a smaller reporting company, we are not required to provide a "Compensation Discussion and Analysis" under Item 402 of Regulation S-K.

Summary Compensation Table

The following table sets forth information regarding compensation awarded to or earned by our named executive officers for service during the last two completed fiscal years:

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Retirement of Samuel M. Sato, Interim CEO Appointment, and CEO Appointment

We entered into an employment agreement with Mr. Sato on May 3, 2021, pursuant to which he served as President and Chief Executive Officer, and as a member of our Board of Directors, until his retirement effective on April 25, 2025. Under the employment agreement, we agreed to pay a base salary with an annual opportunity to increase. Mr. Sato was also eligible for participation in the Company's annual incentive bonus plans and grants of equity compensation offered by the Company to its senior executives from time to time.

Effective April 25, 2025, the Board of Directors appointed Mr. S. Schlecht as Interim Chief Executive Officer of the Company in addition to his role as Senior Advisor to the Company. Mr. S. Schlecht received no additional compensation for serving as Interim Chief Executive Officer, and he served in such capacity until May 5, 2025, when Ms. Pugliese joined the Company as President and Chief Executive Officer.

Employment Agreement with Ms. Pugliese

We entered into an employment agreement with Ms. Pugliese effective May 5, 2025, as amended by the First Amendment to Employment Agreement, effective March 9, 2026, between the Company and Ms. Pugliese (as amended, the "Employment Agreement"), pursuant to which she serves as the President and Chief Executive Officer of the Company. Under the Employment Agreement, we agreed to pay a base salary with an annual opportunity to increase. Ms. Pugliese is also eligible for participation in the Company's annual incentive bonus plans and grants of equity compensation offered by the Company to its senior executives from time to time. Ms. Pugliese will serve on our Board of Directors for the duration of her time as President and Chief Executive Officer. The Employment Agreement provides that for fiscal 2026 she is entitled to receive an equity grant with a minimum grant date fair value of $2,300,000, vesting ratably on the first, second and third anniversaries of the grant date, subject to her continuous employment on the respective vesting dates and such other terms and conditions as the Board of Directors and/or its Compensation Committee approve.

Ms. Pugliese and/or her family are entitled to participate in all applicable qualified and nonqualified retirement plans, and all applicable welfare benefit plans to the same extent as our other senior executives. Ms. Pugliese is also entitled to 200 hours of "paid time off" (i.e., sick days, personal days and vacation days) per calendar year (pro-rated for partial years). Ms. Pugliese will also be reimbursed for reasonable out-of-pocket expenses incurred in the course of performing her duties for the Company in accordance with the Company's reimbursement policies for senior executives as in effect from time to time.

Ms. Pugliese's employment will be terminated under the following circumstances: (i) immediately upon her death or determination of "disability;" (ii) immediately for "cause" subject to the Company giving her written notice stating the basis of such termination; (iii) upon her voluntary termination other than with "good reason," with 45 days prior notice, or at such other earlier time as may be mutually agreed by the Company and her; (iv) immediately by the Company without "cause" upon the Company providing notice to her; and (v) her termination for "good reason" at which time her employment and all the Company's obligations under the Employment Agreement will terminate except as specifically provided.

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If Ms. Pugliese is terminated due to death or "disability," she will have the right to receive: (a) any unpaid base salary with respect to the period prior to the effective date of termination, (b) payment of any accrued but unused paid time off, (c) all vested benefits to which she is entitled under applicable benefit plans, (d) reimbursement of expenses in accordance with the Company's reimbursement policies (clauses (a)-(d) collectively, the "Accrued Obligations"), and (e) provided that she, or a representative of her estate, executes and delivers to us an irrevocable release of all employment-related claims against the Company, a pro-rated annual incentive bonus payment (based on the number of days worked in that fiscal year) for the fiscal year in which termination occurs based on actual performance-based bonus attainments for such fiscal year, payable in a lump sum. If Ms. Pugliese is terminated for "cause" or voluntarily terminates her employment other than with "good reason," she will have no further rights against us, except for the right to receive the Accrued Obligations. If her employment is terminated without "cause" or she resigns with "good reason" and such termination does not occur within the period that begins 30 days prior to a "change in control" and ends two years following a "change in control", then Ms. Pugliese will have no further rights against the company except to receive the Accrued Obligations and "severance payments," but only for so long as she complies with certain confidentiality, non-competition and non-solicitation restrictions for a specified period of time after employment. "Severance payments" means twelve months of base salary continuation for Ms. Pugliese and a pro-rated annual incentive bonus payment (based on the number of days worked in that fiscal year) for the fiscal year in which termination occurs based on actual performance-based bonus attainments for such fiscal year. To the extent it does not result in a tax or penalty on the Company, "severance payments" also means reimbursement for the portion of the premiums paid by Ms. Pugliese to obtain COBRA continuation health coverage that equals the Company's subsidy for health coverage for active employees (including family coverage, if applicable) for twelve (12) months, following the termination of her employment. Additionally, Ms. Pugliese's annual incentive bonus and the treatment of her equity awards will be governed by the terms of the applicable plans or grant agreements. If Ms. Pugliese is terminated "without cause" or for "good reason" during a "change in control period", then Ms. Pugliese will have no further rights against the Company except to receive the Accrued Obligations and "change in control severance payments", which includes (A) a lump-sum payment of two and one-half times the sum of (x) twelve (12) months of base salary and (y) annual target bonus for the fiscal year in which termination occurs, and (B) COBRA continuation payments for eighteen (18) months following the date employment terminates.

Under the Employment Agreement, we may compute whether there would be any "excess parachute payments" payable to Ms. Pugliese within the meaning of Section 280G of the Internal Revenue Code of 1986, as amended (the "Code"), payable to her under her Employment Agreement or any other plan, agreement or otherwise. If there would be any excess parachute payments, we, based on the advice of our legal or tax counsel, will compute the net after-tax proceeds related to such parachute payments, taking into account the excise tax imposed by Section 4999 of the Code, as if (i) such parachute payments were reduced, but not below zero, such that the total parachute payments payable to Ms. Pugliese would not exceed three times the "base amount" as defined in Section 280G of the Code, less one dollar; or (ii) the full amount of such parachute payments were not reduced. If reducing the amount of such parachute payments otherwise payable would result in a greater after-tax amount to Ms. Pugliese such reduced amount will be paid to her and the remainder will be forfeited. If not reducing such parachute payments otherwise payable would result in a greater after-tax amount to her, then such parachute payments will not be reduced.

The Employment Agreement includes certain confidentiality, non-competition and non-solicitation restrictions during the term of employment and for a specified period of time thereafter.

Inducement Stock Award Agreement and Inducement Restricted Stock Award Agreement for Ms. Pugliese

In connection with Ms. Pugliese's hiring as our President and Chief Executive Officer, the Company granted an aggregate of 1,759,532 shares of Class B common stock to Ms. Pugliese pursuant to the terms of the Inducement Stock Award Agreement and the Inducement Restricted Stock Award Agreement, entered between the Company and Ms. Pugliese on May 5, 2025.

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The Company granted 586,511 shares pursuant to the Inducement Stock Award Agreement to Ms. Pugliese on May 5, 2025 subject to repayment in connection with certain termination of employment. If Ms. Pugliese terminates her employment without good reason or is terminated by the Company for cause prior to May 5, 2026, she will be required to reimburse the Company for a pro rata portion of the 586,511 shares granted to Ms. Pugliese under such agreement.

In connection with the 1,173,021 shares of restricted stock granted to Ms. Pugliese pursuant to the Inducement Restricted Stock Award Agreement, (i) 33% of such shares will vest on May 5, 2026, (ii) 33% of such shares will vest on May 5, 2027, and (iii) the remaining 34% of the shares will vest May 5, 2028. If Ms. Pugliese's employment with the Company is terminated (i) due to her death, (ii) due to her disability, (iii) without cause, or (iv) by Ms. Pugliese for good reason, then all unvested stock will vest immediately. If her employment with the Company is terminated for any other reason, all unvested stock will be forfeited and revert to the Company.

The stock awards were granted outside the terms of the Company's 2024 Equity Incentive Plan and were approved by the Company's Board of Directors, Compensation Committee, and the Subcommittee of the Compensation Committee of the Board of Directors, consisting of the independent directors of the Compensation Committee, in reliance on the employment inducement exemption under NASDAQ Listing Rule 5635(c)(4).

Employment Agreement with Mr. S. Schlecht

We entered into an employment agreement with Mr. S. Schlecht on August 5, 2015, which was further amended and restated on May 27, 2021 and subsequently amended on February 26, 2025 and on June 9, 2025 (as amended, the "Schlecht Employment Agreement"). From April 25, 2025 to May 5, 2025, Mr. S. Schlecht also served as our Interim Chief Executive Officer. In accordance with the Schlecht Employment Agreement, Mr. S. Schlecht is eligible for participation in the Company's annual incentive bonus plans offered by the Company to its senior executives from time to time. Mr. S. Schlecht will serve on our Board of Directors for the duration of his term as Senior Advisor.

Pursuant to the amendment on June 9, 2025, the Company and Mr. S. Schlecht agreed to reduce Mr. S. Schlecht's salary from $275,000 to $50,000 from June 9, 2025 through February 1, 2026. Such reduction in base salary does not constitute "Good Reason" under the Schlecht Employment Agreement. On February 2, 2026, Mr. S. Schlecht's base salary under the Schlecht Employment Agreement automatically increased from $50,000 to $275,000. Furthermore, the Schlecht Employment Agreement provides that for purposes of determining Mr. S. Schlecht's participation in the bonus plan for fiscal year 2025, the amount of his bonus amount would be calculated using a base salary of $275,000.

On March 9, 2026, the Company and Mr. S. Schlecht entered into the Fourth Amendment to the Schlecht Employment Agreement, effective March 16, 2026 (the "Fourth Amendment"). The Fourth Amendment extends the term of the Schlecht Employment Agreement through the annual meeting of shareholders in 2028. In addition, the Fourth Amendment reduces Mr. S. Schlecht's annual base salary from $275,000 to $100,000, and provides that his existing bonus target of 50% of his base salary and maximum bonus of 75% of his base salary under the Company's annual incentive bonus plans is applicable for fiscal years 2026 through 2028, with a prorated bonus for fiscal year 2028.

Offer Letters

Ms. Agrawal and Mr. Homolka are not party to an employment agreement with us but received compensation in accordance with their offer letters with the Company, which describe the elements of their compensation, including base salary, short- and long-term incentive opportunities and eligibility to participate in the Company's healthcare and other benefit plans. Each element of compensation for these NEOs is subject to review and approval by the Compensation Committee.

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Inducement Restricted Stock Award Agreement for Ms. Agrawal

Ms. Agrawal and the Company entered into an Inducement Restricted Stock Award Agreement on February 12, 2024, whereby the Company granted 94,000 shares of restricted stock with a grant date of February 12, 2024, as a material inducement to Ms. Agrawal's hiring. The restricted stock vest in two tranches-one half on February 12, 2024, her first day of employment (the "First Tranche Shares"), and one half on the third anniversary of the first day of her employment (the "Second Tranche Shares"). The First Tranche Shares are subject to repayment by Ms. Agrawal if Ms. Agrawal voluntarily terminates her employment or is terminated for cause as follows: (i) prior to the 12-month anniversary of the grant date, 100% of the First Tranche Shares will be forfeited; (ii) on or after the 12-month anniversary of the grant date and before the 24-month anniversary of the grant date, 75% of the First Tranche Shares will be forfeited; and (iii) on or after the 24-month anniversary of the grant date and prior to the 36-month anniversary of the grant date, 50% of the First Tranche Shares will be forfeited. The Second Tranche Shares are subject to Ms. Agrawal's continued employment on the third anniversary of her first day of employment.

The restricted stock was granted outside the terms of the Company's 2015 Equity Incentive Plan and was approved by the Company's Board of Directors, Compensation Committee, and the Subcommittee of the Compensation Committee of the Board of Directors, consisting of the independent directors of the Compensation Committee, in reliance on the employment inducement exemption under NASDAQ Listing Rule 5635(c)(4).

Bonus Payouts and Annual Incentive Plan

We remain committed to setting our goals to align with delivering strong financial performance.

Fiscal 2024 Bonus:

For fiscal 2024, and under our Annual Incentive Plan, the target award for Mr. Sato was 100% of his base salary, and the target award for Ms. Agrawal was 65% of her base salary. Adjusted EBITDA was the performance measure for Mr. Sato and Ms. Agrawal, which accounted for 100% of their annual incentive opportunity. The Adjusted EBITDA threshold outcomes for fiscal 2024 were not achieved. Accordingly, we did not pay an annual incentive payout to our NEOs in fiscal 2024.

Fiscal 2025 Bonus:

For fiscal 2025, and under our Annual Incentive Plan, the target awards for Mr. Sato and Ms. Pugliese were 100% of their base salaries, the target award for Mr. S. Schlecht was 75% of his base salary, and the target awards for Ms. Agrawal and Mr. Homolka were 65% of their base salaries. The performance measure for fiscal 2025 was Adjusted EBITDA, which accounted for 100% of NEOs' annual incentive opportunity. The Adjusted EBITDA outcome for fiscal 2025 was achieved. The applicable fiscal 2025 bonus payouts are reflected in the "Nonequity Incentive Plan Compensation" column in the Summary Compensation Table on page 17.

Annual Incentive Plan

We adopted the Annual Incentive Plan of Duluth Holdings Inc., which became effective February 1, 2016 and was approved by our shareholders in advance of our IPO. The Compensation Committee approved amendments to the Annual Incentive Plan on February 21, 2018 to reflect the Tax and Jobs Act of 2017's repeal of the performance-based compensation exception under Section 162(m) of the Internal Revenue Code of 1986, as amended, and on February 20, 2024 to provide the Company with additional flexibility to make awards requiring employment beyond the end of the applicable fiscal year. The following is a description of the material features and provisions of our Annual Incentive Plan.

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Objectives. Our Annual Incentive Plan permits us to establish a correlation between compensation and the financial performance of our Company by providing annual cash compensation to participants based on the achievement of specified performance goals.

Administration and Eligibility. The Annual Incentive Plan is administered by our Compensation Committee. The Compensation Committee has full power and authority to select the participants to whom awards will be granted and to determine the specific terms and conditions of each award, subject to the provisions of the Annual Incentive Plan.

Awards. The Annual Incentive Plan provides for the grant of incentive awards, which entitle the participant to receive a cash award upon the attainment of specified performance goals for a given fiscal year. The Compensation Committee may specify one or more performance goals applicable to a participant for a given fiscal year. The Compensation Committee will establish a threshold, target, and maximum level of achievement for the specified performance goal(s) applicable to a participant's incentive award that will yield a corresponding threshold, target, or maximum award opportunity payable in cash. Unless otherwise determined by the Compensation Committee at the time the award opportunities are established, achievement of a performance goal between the various levels of achievement for the specified performance goal(s) will result in a payout that is linearly interpolated between the threshold and target opportunities and between the target and maximum opportunities.

The performance goals will be any one or more of the following performance criteria (the "Performance Goals"), either individually, alternatively or in any combination, applied to either the Company as a whole or to a business unit or subsidiary, and measured either annually or cumulatively over a period of years, on an absolute basis or relative to a pre-established target, to previous years' results or to a designated comparison group, in each case as specified by the Compensation Committee in the award: net income; revenue; earnings per share; return on investment; return on invested capital; return on equity; return on assets or net assets; shareholder returns (either including or excluding dividends) over a specified period of time; financial return ratios; cash flow (including, but not limited to, operating cash flow, free cash flow, cash flow return on equity, and cash flow return on investment); amount of expense; economic profit; gross profit; gross profit margin percentage; operating profit; operating profit margin percentage; amount of indebtedness; debt ratios; earnings before bonus, interest, taxes, depreciation, amortization or stock based compensation (or any combination thereof); share value; return on capital employed; return on average capital employed; strategic business criteria, consisting of one or more objectives based on achieving specified revenue, market penetration, or geographic business expansion goals, or cost targets, or goals relating to acquisitions or divestitures, or any combination of the foregoing; customer satisfaction; productivity ratios; new product invention or innovation; attainment of research and development milestones; or such other subjective or objective performance measures, including individual goals deemed appropriate by the Compensation Committee.

The Compensation Committee may specify any reasonable definition of the above criteria at the time it sets the goals for an award.

Even if the Performance Goals applicable to a participant have been met, (i) no Incentive Award to such participant with respect to a performance year shall exceed $5,000,000, and (ii) the Compensation Committee expressly reserves, in its discretion, the right to adjust any Incentive Award otherwise determined under the Annual Incentive Plan to reflect any extraordinary items or such other factors as it may deem relevant if it determines it is in the best interests of the Company to do so.

Participants. Except as otherwise set forth in a written agreement between us and a participant or as determined by the Compensation Committee, a participant shall receive no incentive award for a year if the participant's employment with the company terminates prior to the last day of the fiscal year for which an award is applicable for any reason.

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Executive Officer Compensation Recovery Policy

The Company maintains an executive officer compensation recovery policy. Pursuant to this policy, the Company shall recover from its executive officers erroneously awarded compensation that was based on an accounting restatement. The Compensation Committee administers the policy and must determine promptly (in no event later than 90 days after the restatement date) the amount of any erroneously awarded compensation that each executive officer received during the clawback period and provide written notice of the amount to such executive officer demanding repayment.

Stock Ownership Policy

The Company maintains stock ownership guidelines requiring officers and directors to own and hold shares of Class B common stock of the Company to further align their interests with the long-term interests of shareholders. Officers and directors must own shares of Class B common stock of the Company with an aggregate value equal to or greater than the applicable amount in the following schedule:

Shares of Class B common stock held by an officer or director in any of the following forms count toward a participant's satisfaction of the applicable minimum ownership requirements: (i) shares owned directly, (ii) shares owned indirectly (e.g., by immediate family members or in a trust), and (iii) time-vested restricted stock.

Officers and directors have five years to meet the applicable ownership requirement, measured from the later of the adoption of the policy or the date such participant is first appointed as a vice president, senior vice president or director. Participants promoted to higher-level positions with an increased stock ownership requirement have five years from the date of promotion to meet the applicable ownership requirement.

Any participant who has not met the applicable minimum ownership requirement is required to retain fifty percent of the net after-tax shares received by a participant upon exercise or vesting of awards received under the Company's equity incentive plan. Compliance is reviewed annually by the Compensation Committee. All officers and directors subject to the guidelines currently comply with the Company's stock ownership guidelines.

Outstanding Equity Awards at Fiscal Year End 2025 Table

The following table sets forth information regarding outstanding equity awards held by each of our named executive officers as of February 1, 2026:

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2024 Equity Incentive Plan

We adopted the 2024 Equity Incentive Plan of Duluth Holdings Inc., which was effective following approval by our shareholders on May 23, 2024 (the "2024 Plan").

Objectives: Our 2024 Plan permits us to provide compensation alternatives such as stock options, shares, restricted stock awards, restricted stock unit awards, and performance share awards, using or based on our Class B common stock.

Administration: The 2024 Plan is administered by the Compensation Committee, subject to other provisions within the 2024 Plan. Subject to any express limitations set forth in the 2024 Plan, the Compensation Committee has full and exclusive discretionary power and authority to take such actions as it deems necessary and advisable with respect to the administration of the 2024 Plan.

Shares Subject to the 2024 Plan: As of February 1, 2026, there were a total of 4,042,933 shares of Class B common stock authorized for issuance under the 2024 Plan. In determining the number of shares available for grant under the 2024 Plan at any time, the following rules shall apply:

Awards: The 2024 Plan permits us to provide compensation alternatives such as stock options, shares, restricted stock awards, restricted stock unit awards, and performance share awards, using or based on our Class B common stock.

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Eligibility: Individuals eligible to participate in the 2024 Plan shall be limited to employees, non-employee directors and third-party service providers of the Company.

Participation: Subject to provisions of the 2024 Plan, the Compensation Committee may, from time to time, select from all individuals eligible to participate in the 2024 Plan, those individuals to whom awards shall be granted and shall determine, in its sole discretion, the nature of any and all terms permissible by law and the amount of each award. In accordance with the terms of his Employment Agreement, as amended, Mr. S. Schlecht is not eligible for grants of equity compensation under the 2024 Plan.

Effective Date and Duration: The 2024 Plan became effective as of May 23, 2024, and will remain in effect for ten years from the effective date unless terminated sooner. At any time, the Board of Directors may terminate the 2024 Plan. However, any termination will not affect outstanding awards.

Transferability: Non-vested stock granted under an award may not be transferred until the restrictions on such stock as set forth in the applicable award agreement have expired.

Amendments: The Board of Directors at any time, and from time to time, may amend or terminate the 2024 Plan. However, no amendment will be effective unless approved by the shareholders of the Company to the extent shareholder approval is necessary to satisfy any applicable law, regulation or exchange requirement.

Forfeiture and Recoupment Events: The Compensation Committee may specify in an award agreement that the participant's rights, payments and benefits with respect to an award shall be subject to reduction, cancellation, forfeiture or recoupment upon the occurrence of certain specified events, in addition to any otherwise applicable treatment of an award. Awards and any compensation directly attributable to awards shall be subject to forfeiture, recovery by the Company or other action pursuant to any compensation recovery policy adopted by the Board of Directors or the Compensation Committee at any time, including in accordance with the Company's Executive Officer Compensation Recovery Policy, or as otherwise required by law and any award agreement may be unilaterally amended by the Compensation Committee to comply with any such compensation recovery policy.

Executive Change in Control Severance Plan and Executive General Severance Plan

The Compensation Committee adopted and approved the Duluth Holdings Inc. Executive Change in Control Severance Plan (the "Change in Control Severance Plan") and the Duluth Holdings Inc. Executive General

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Severance Plan (the "General Severance Plan", and together with the Change in Control Severance Plan, the "Severance Plans"). Ms. Agrawal and Mr. Homolka, in addition to other executive officers, are participants in the Severance Plans. Ms. Pugliese, Mr. Sato and Mr. S. Schlecht were not designated as a participant in the Severance Plans, and Ms. Pugliese and Mr. Sato are entitled to severance benefits under their respective employment agreements. Participants in our Severance Plans are not entitled to receive a duplication of severance benefits. In the event that a participant is a participant in the Company's General Severance Plan at the time of a qualifying termination under the Change in Control Severance Plan, no benefits shall be payable to such participant under the Company's General Severance Plan and such participant will only be eligible for the severance benefits payable under the Change in Control Severance Plan.

Executive General Severance Plan:

The General Severance Plan provides severance benefits to those individuals selected as participants by the Compensation Committee of the Board of Directors.

If a participant incurs a qualifying termination, then the participant would be entitled to receive severance benefits. A participant would not be entitled to receive severance benefits if the participant's employment with the Company ends for reasons other than a qualifying termination. A qualifying termination means a termination of employment from the Company and its affiliates that occurs under the following circumstances: (1) an involuntary termination of a participant's employment by the Company for reasons other than cause or death pursuant to a notice of termination delivered to the participant by the Company no later than thirty days prior to the participant's termination of employment, or (2) a voluntary termination by participant for good reason pursuant to a notice of termination delivered to the Company by participant in accordance with the General Severance Plan.

In the event a participant becomes entitled to receive severance benefits, the Company shall provide the participant with the following:

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The treatment of any awards under the Company's equity incentive plans that may be outstanding on the participant's effective date of termination shall be determined under the applicable equity incentive plan under which the award was granted and the related award agreement.

As a condition to participating, a participant must sign a restrictive covenant agreement prior to receiving any severance benefits. If a participant breaches any of the covenants, the Committee may, in its sole discretion, determine that the participant (i) shall forfeit any unpaid portion of the payments or benefits provided and/or (ii) shall repay to the Company any amounts previously paid to the participant pursuant to the General Severance Agreement.

Executive Change in Control Severance Plan:

The Change in Control Severance Plan provides severance benefits to those individuals selected as participants by the Compensation Committee of the Board of Directors.

If a participant incurs a qualifying termination, then the participant would be entitled to receive severance benefits. A participant would not be entitled to receive severance benefits if the participant's employment with the Company ends for reasons other than a qualifying termination. A qualifying termination means a termination of employment from the Company and its affiliates under the following circumstances: (1) an involuntary termination of a participant's employment by the Company for reasons other than cause or death pursuant to a notice of termination delivered to the participant by the Company within six months prior to or upon or within 24 months after a change in control, or (2) a voluntary termination by a participant for good reason pursuant to a notice of termination delivered to the Company by the participant within six months prior to or upon or within 24 months after a change in control.

In the event a participant becomes entitled to receive severance benefits, the Company shall provide the participant with the following:

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Similar to the General Severance Plan, a participant must sign a restrictive covenant agreement prior to receiving any severance benefits, and the treatment of any awards under the Company's equity incentive plans that may be outstanding on the participant's effective date of termination shall be determined under the applicable equity incentive plan under which the award was granted and the related award agreement.

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DIRECTOR COMPENSATION

Under our current outside director compensation policy, our non-employee directors receive a $50,000 annual cash retainer. For service on the Audit Committee, a non-employee director receives an additional $10,000 annual cash retainer. For service on the Compensation Committee and Nominating and Governance Committee, a non-employee director receives an additional $7,000 annual cash retainer. In lieu of the annual cash retainer for committee participation, each non-employee director serving as a chair of a board committee receives the following annual cash retainer: $20,000 for Audit Committee chair; $15,000 for Compensation Committee chair; and $12,000 for Nominating and Governance Committee chair. Each non-employee director also receives an annual restricted stock grant of $80,000 of Class B common stock under the 2024 Equity Incentive Plan based on the fair market value of the Class B common stock on the date of grant, which vests on the first anniversary of the date of grant.

At least ten days before the start of the fiscal year, each non-employee director may elect to receive unrestricted Class B common stock in lieu of their annual cash retainers for the fiscal year. A non-employee director's election to receive stock in lieu of cash may cover 25%, 50%, 75% or 100% of their annual cash retainers for the fiscal year. Grants are expected to be made in May of each year. Prorated grants will be made for partial years of service. All of our directors are reimbursed for reasonable travel and other expenses incurred in connection with attending board and committee meetings.

The following table sets forth information concerning compensation paid to our non-employee directors during the fiscal year ended February 1, 2026, for their service on our Board of Directors. Directors who are also our employees received no additional compensation for their service as directors and are not included in the table below.

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As of February 1, 2026, the aggregate number of unvested shares of restricted stock held by each incumbent non-employee director was as follows:

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SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS

The following table sets forth certain information with respect to the beneficial ownership of our Class A and Class B common stock as of the record date (except as otherwise noted) for:

We have determined beneficial ownership in accordance with the rules of the SEC. Under these rules, beneficial ownership includes any shares as to which the individual or entity has sole or shared voting power or investment power, as well as shares that may be acquired within 60 days of the record date. There are no shares of common stock subject to options or other rights outstanding as of the date of this proxy statement. Except as indicated by the footnotes below, we believe, based on the information furnished to us, that persons and entities named in the table below have sole voting and investment power with respect to all the capital stock that they beneficially own, subject to applicable community property laws.

Applicable percentage ownership is based on 3,364,200 shares of Class A common stock outstanding and 34,764,498 shares of Class B common stock outstanding as of the record date, as well as shares which may be acquired within 60 days of the record date. Unless otherwise indicated, the address of each beneficial owner in the table is: Duluth Holdings Inc., 201 East Front Street, Mount Horeb, Wisconsin 53572.

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PROPOSAL THREE: RATIFICATION OF INDEPENDENT REGISTERED PUBLIC ACCOUNTANTS

The Audit Committee has appointed KPMG LLP ("KPMG"), independent registered public accountants, to audit our consolidated financial statements for the fiscal year ending January 31, 2027 and has recommended to the Board of Directors that such appointment be submitted to the shareholders for ratification. KPMG has audited our financial statements since fiscal 2022. Representatives of KPMG will be present at the annual meeting, will have an opportunity to make a statement if they so desire, and also will be available to respond to appropriate questions from shareholders.

If shareholders do not ratify the appointment of KPMG, the Audit Committee will take such action into account in reconsidering the appointment of our independent auditors for the fiscal year ending January 31, 2027.

The affirmative vote of a majority of the votes cast on this proposal shall constitute ratification of KPMG as our independent auditors for the fiscal year ending January 1, 2027. Abstentions and broker non-votes will not be counted as votes cast and, therefore, will have no impact on the approval of the proposal.

The Board of Directors unanimously recommends that you vote FOR the ratification of the appointment of KPMG LLP as our independent registered public accountants for the fiscal year ending January 31, 2027, and your proxy will be so voted unless you specify otherwise.

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AUDIT COMMITTEE REPORT

In accordance with its written charter, the Audit Committee oversees all accounting and financial reporting processes and the audit of our financial statements. The Audit Committee assists the Board of Directors in fulfilling its responsibility to our shareholders, the investment community and governmental agencies relating to the quality and integrity of our financial statements and the qualifications, independence and performance of our independent registered public accountants. During fiscal 2025, the Audit Committee held five meetings and discussed the interim financial information contained in each of our quarterly reports on Form 10-Q with the chief financial officer and interim chief accounting officer, director of financial reporting, director of internal audit and independent registered public accountants prior to their filing with the SEC. The Audit Committee has appointed KPMG to serve as our independent registered public accountants for fiscal 2026.

Independent Registered Public Accountants Independence and Fiscal 2025 Audit. In discharging its duties, the Audit Committee obtained from KPMG, our independent registered public accountants for the fiscal 2025 audit, a formal written statement describing all relationships between KPMG and us that might bear on KPMG's independence in accordance with the applicable requirements of the Public Company Accounting Oversight Board ("PCAOB"). In addition, the Audit Committee discussed with KPMG any relationships that may impact KPMG's objectivity and independence and satisfied itself as to KPMG's independence. The Audit Committee also independently discussed with management and KPMG the quality and adequacy of our internal controls, and reviewed with KPMG its audit plans, audit scope and identification of audit risks.

The Audit Committee discussed and reviewed with KPMG the matters required to be discussed by the applicable requirements of PCAOB and the Securities and Exchange Commission and, with and without management present, discussed and reviewed the results of KPMG's fiscal 2025 audit of the financial statements.

Fiscal 2025 Financial Statements and Recommendations of the Committee. The Audit Committee separately reviewed and discussed our audited financial statements and management's discussion and analysis of financial condition and results operations ("MD&A") as of and for the fiscal year ended February 1, 2026 with management and KPMG. Management has the responsibility for the preparation of our financial statements and the independent registered public accountants have the responsibility for the examination of those statements.

Based on the above-mentioned review, and discussions with management and KPMG, the Audit Committee recommended to the Board of Directors that our audited financial statements be included in our annual report on Form 10-K for the fiscal year ended February 1, 2026 for filing with the SEC.

Fees Paid to KPMG. The aggregate fees billed for professional services by KPMG during fiscal years 2024 and 2025 were approximately as follows:

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All audit services provided by KPMG were approved by the Audit Committee.

In performing all of the functions described above, the Audit Committee acts only in an oversight capacity. The Audit Committee may not complete its reviews of the matters described above prior to our public announcement of financial results and, necessarily, in its oversight role, the Audit Committee relies on the work and assurances of the Company's management, which has the primary responsibility for the Company's financial statements and reports and internal control over financial reporting, and of the independent auditors, who, in their report, express an opinion on the conformity of the Company's annual financial statements to accounting principles generally accepted in the United States.

The Audit Committee:

Susan J. Riley (Chair)

David C. Finch

Janet H. Kennedy

Brett L. Paschke

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SUBMISSION OF SHAREHOLDER PROPOSALS

Proposals of a shareholder submitted pursuant to Rule 14a-8 of the SEC ("Rule 14a-8") for inclusion in the proxy statement for the 2027 Annual Meeting of Shareholders must be received by Duluth Trading at its executive offices no later than December 22, 2026. A shareholder who intends to present business other than pursuant to Rule 14a-8 at the 2027 Annual Meeting must comply with the requirements set forth in our amended and restated bylaws. To bring shareholder proposed nominations or other business before an annual meeting, our amended and restated bylaws require, among other things, that the shareholder submit written notice thereof to Duluth Trading's executive offices not less than 90 days nor more than 120 days prior to the anniversary of the annual meeting of shareholders held the prior year. Therefore, we must receive notice of a shareholder proposal submitted other than pursuant to Rule 14a-8 no earlier than February 3, 2027 and no later than March 5, 2027. If notice is received before February 3, 2027, or after March 5, 2027, it will be considered untimely, and Duluth Trading will not be required to allow the proposal to be presented at the 2027 Annual Meeting of Shareholders.

Such nominations or proposals must be submitted to Corporate Secretary, Duluth Holdings Inc., 201 East Front Street, Mount Horeb, Wisconsin 53572. To avoid disputes as to the date of receipt, it is suggested that any shareholder proposal be submitted by certified mail, return receipt requested.

In addition to satisfying the foregoing requirements under our bylaws, to comply with the universal proxy rules for the 2027 Annual Meeting of Shareholders, shareholders who intend to solicit proxies in support of director nominees other than the Company's nominees must provide notice that sets forth the additional information required by Rule 14a-19 under the Exchange Act no earlier than February 3, 2027 and no later than March 5, 2027.

DELINQUENT SECTION 16(a) REPORTS

Section 16(a) of the Exchange Act requires the Company's directors and officers, among others, to file reports with the SEC disclosing their ownership, and changes in their ownership, of stock in the Company. Copies of these reports must also be furnished to the Company. Based solely on a review of these copies, the Company believes that all filing requirements were complied with on a timely basis during fiscal 2025, except for a Form 4 filing related to an award of Class B common stock for each of Ms. Kennedy and Mr. Williams due to administrative delay.

OTHER MATTERS

Although management is not aware of any other matters that may come before the annual meeting, if any such matters should be presented, the persons named in the enclosed proxy card intend to vote as recommended by the Board of Directors or, if no such recommendation is given, in accordance with their best judgment.

Shareholders may obtain a free copy of our annual report on Form 10-K for fiscal 2025 at no cost by writing to Corporate Secretary, Duluth Holdings Inc., 201 East Front Street, Mount Horeb, Wisconsin 53572.

By Order of the Board of Directors,

Duluth Holdings Inc.

Wenyu Blanchard

Corporate Secretary

Mount Horeb, Wisconsin

April 21, 2026

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DYLUTH TRADING CO VOTE Using a black iin pen, mark your votes wilth an X as shown in this example Piease do not wile outside the desigaled ares. 2026 Annual Meeting Proxy Card V IF VOTING BY MAIL, SIGN, DETACH AND RETURN THE BOTTOM PORTION IN THE ENCLOSED ENVELOPE.V Proposals-The Board of Directors recommends a vote FOR all nominees and FOR Proposals 2 and 3. Proposals 1, 2 and 3 are being proposed by Duluth Holdings Inc. 1. Election of Diirectors: Your vote matters-here's how to vote! You may vote online or by phone instead of mailing this card. Votes submitted electronically must be received by June 3, 2026 at 1:00 a.m., Central Time. Online Go to www.envisionreports.com/DLTH or scan the QR code-login details are located in the shaded bar below. Phone Call toll free 1-800-652-VOTE (8683) within the USA, US territories and Canada Save paper, time and money! Sign up for electronic delivery at www.envisionreports.com/DLTH A Withh old For Authority + Withho lld For Authority Wit hhold For Authority 01-Stephen L. Schlecht 04-Janet H. Kennedy O7-Ronalld Robinson 2. To approve, by an advisory vote, the compensation of our named executive officers. 02-Stephanie L Pugliese 05- Brett L. Paschke 08-Scott K. Williams For 03-David C. Finch 06-Susan J. Rilley Against Abstain 3. To ratify the appointment of KPMG LLP as our independent registered public accoun tants for fiscall 2026. For Against Abstain NOTE: In their discretion, the proxies are authorized to consider and vote upon any other matters which may properly come before the meeting or any adjournment thereof. B Date (mm/dd/yyyy)-Please print date bellow. / Signature 1- Please keep signature within the box. Authorized Signatures-This section must be completed for your vote to count. Please date and sign below. Please sign exactly as name(s) appears hereon. Joint owners should each sign. When signing as attorney, executor, administrator, corporate officer, trustee, guardian, or custodian, pllease give fulll title. Signature 2-Please keep signature within the box. 1UPX +

2026 Annual Meeting Admission Ticket 2026 Annual Meeting of Duluth Holdings Inc. Shareholders Wednesday, June 3, 2026, 8:30 a.m. Central Time Duluth Holdings Inc. 201 East Front Street, Mount Horeb, Wisconsin 53572 Upon arrival, please present this admission ticket and photo identification at the registration desk. The 2026 Annual Meeting of Shareholders of Duluth Holdings Inc. will be held on We dnesday, June 3, 2026, 8:30 a.m. Central Time Important notice regarding the Internet availability of proxy materials for the Annual Meeting of Shareholders. The material is available at: www.envisionreports.com/DLTH Small steps make an impact. Help the environment by consenting to receive electronic delivery, sign up at www.envisionreports.com/DLTH IF VOTING BY MAIL, SIGN, DETACH AND RETURN THE BOTTOM PORTION IN THE ENCLOSED ENVELOPE.V Duluth Holdings Inc. Notice of 2026 Annual Meeting of Shareholders Proxy Solicited by Board of Directors for Annual Meeting-June 3, 2026 The undersigned hereby appoints Stephanie L. Pugliese and Wenyu Blanchard, and each or either of them, as true and lawful attorneys of the undersigned with full power of substitution and revocation, and authorizes them, and each of them, to vote all the shares of capital stock of Duluth Holdings Inc., which the undersigned is entitled to vote at said meeting or any adjoumment thereof upon the matters specified and upon such other matters as may be properly brought before the meeting or any adjournment there of, conferring authority upon such true and lawful attorneys to vote in their discretion on such matters as may properly come before the meeting and revoking any proxy heretofore given. Shares represented by this proxy will be voted as directed by the shareholder. If no such directions are indicated, the Proxies will have authority to vote FOR all nominees in Proposal 1 and FOR Proposals 2 and 3. (Items to be voted appear on reverse side) + Non-Voting Items Change of Address-Please print new addre ss bellow. Comments-Please print your comments bellow. +