June 29, 2026

Mr. Andrew McLean
c/o Lands’ End, Inc.
5 Lands’ End Lane
Dodgeville, WI 53595

Re: Transition and Advisory Services

Dear Andrew:

On behalf of Lands’ End, Inc. (the “Company”) and its Board of Directors (the “Board”), I want to thank you for your years of service to the Company, during which you have made many meaningful contributions. This letter agreement (this “Letter Agreement”) sets forth the terms of your separation from service with the Company.

Effective as of July 13, 2026 (the “Transition Date”), your service as Chief Executive Officer of the Company, as a member of the Board, as a member of the board of managers of LE Topco, LLC, and in any other positions you may hold with the Company or any of its affiliates (including LE Topco, LLC) shall cease, and you hereby resign from such positions; provided, however, that, during the period from July 13, 2026 until September 11, 2026 (or such earlier date as is determined by the Company, the “Termination Date” and such period, the “Transition Period”), you shall serve as a non-corporate officer employee of the Company. While such resignations are intended to be self-effectuating, you further agree to execute any documentation that the Company determines necessary or appropriate to facilitate such resignation. Any statements relating to your separation from service in any Company-issued press release announcing your separation from service will be substantially consistent with a draft reviewed (and, if you desire, commented on) by you prior to issuance.

During the Transition Period, you shall assist with the transition of your duties as Chief Executive Officer to your successor and with such other matters as may be reasonably requested by the Chief Executive Officer from time to time, provided that (i) such transition services are commensurate with your position as former Chief Executive Officer, (ii) you shall not be required to report to anyone other than your successor Chief Executive Officer or the Board and (iii) any travel required will be mutually agreed upon by you and the Company (and you shall be reimbursed for all reasonable travel expenses). In consideration for such transition services, during the Transition Period you shall continue to (a) receive your annual base salary at the rate in effect as of the date hereof, (b) participate in the health, welfare and retirement plans of the Company and its affiliates in which you currently participate and (c) receive the equity award treatment described in Exhibit B hereto. Effective as of the Termination Date, your employment with the Company and its affiliates shall terminate.

In connection with your termination of employment, and in consideration for your service to the Company and its affiliates through the Termination Date and your compliance with the terms of this Letter Agreement, specifically including your execution of a release agreement substantially in the form attached as Exhibit A and your non-revocation of such release agreement prior to its becoming effective and irrevocable within 30 days following the Termination Date (the “Release Requirement”), and your

compliance with the restrictive covenants set forth in that certain Executive Severance Agreement, dated as of September 6, 2022, by and between you and the Company (the “Executive Severance Agreement”) or in any other agreement between you and the Company or its affiliates, you shall be eligible for the payments and benefits set forth on Exhibit B (the “Severance Benefits”).

The Severance Benefits shall be in full satisfaction of the obligations of the Company and its affiliates to you under this Letter Agreement, the Executive Severance Agreement, and any other plan, agreement, policy or arrangement of the Company and its affiliates upon your termination of employment (other than any director and officer indemnification rights and any vested or other rights to which you may be entitled under any other Company employee benefit or compensation plan by reason of your employment with the Company that cannot legally be waived), and in no event shall you be entitled to severance pay or benefits beyond the Severance Benefits.

Nothing in this Letter Agreement shall prohibit the Company from terminating your employment prior to the Termination Date for “Cause” (as defined in the Executive Severance Agreement) or you from voluntarily terminating your employment prior to the Termination Date; provided that, in each such case, you shall be eligible only for the Accrued Accounts (as defined in Exhibit B) (other than, upon a termination for Cause or resignation without Good Reason, the pro rata cash bonus otherwise be payable under the Company’s Annual Incentive Plan for the 2026 fiscal year), and any other vested or other rights to which you may be entitled under any other Company employee benefit or compensation plan by reason of your employment with the Company that cannot legally be waived and are not otherwise subject to forfeiture upon a voluntary termination without Good Reason. Prior to the termination of your employment for Cause, the Company shall provide you with written notice of the circumstances constituting Cause and shall provide you with ten business days to cure such circumstances (to the extent curable). For the avoidance of doubt, the changes to your role and duties, responsibilities, and authority contemplated by this Letter Agreement and your performance thereof shall not constitute Cause or Good Reason under the Executive Severance Agreement. As of the date hereof, the non-employee members of the Board (for clarity, excluding you) are not aware of any fact or circumstance that would constitute grounds to terminate your employment for Cause.

You hereby reaffirm and agree to comply with the restrictions and obligations set forth in the Executive Severance Agreement or in any other agreement between you and the Company or its affiliates, which remain in full force and effect while employed and for the periods specified therein, as modified by Section 2 hereof. You further agree that payment of the Severance Benefits shall serve as additional consideration for your compliance with such restrictions and obligations.

[Signature Page Follows]

To confirm the foregoing terms are acceptable to you, please execute and return the copy of this Letter Agreement, which is enclosed for your convenience.

Very truly yours,

Lands’ End, Inc.

By: /s/ Josephine Linden
Name: Josephine Linden
Title: Chair, Board of Directors

Acknowledged and agreed:

/s/ Andrew McLean
Andrew McLean

Exhibit A

NOTICE: YOU MAY CONSIDER THIS GENERAL RELEASE AND WAIVER FOR UP TO TWENTY-ONE (21) DAYS. YOU MAY NOT SIGN IT UNTIL ON OR AFTER YOUR LAST DAY OF WORK. IF YOU DECIDE TO SIGN IT, YOU MUST DELIVER A SIGNED COPY TO LANDS’ END, INC. BY NO LATER THAN THE TWENTY-SECOND (22ND ) DAY AFTER YOUR LAST DAY OF WORK TO THE GENERAL COUNSEL, LANDS’ END, INC., 5 LANDS’ END LANE, DODGEVILLE, WISCONSIN 53595. YOU MAY REVOKE THE GENERAL RELEASE AND WAIVER WITHIN SEVEN (7) DAYS AFTER SIGNING. ANY REVOCATION WITHIN THIS PERIOD MUST BE IMMEDIATELY SUBMITTED IN WRITING TO THE GENERAL COUNSEL AT THE ADDRESS SET FORTH ABOVE. YOU MAY WISH TO CONSULT WITH AN ATTORNEY BEFORE SIGNING THIS DOCUMENT.

GENERAL RELEASE AND WAIVER

In consideration of the severance benefits that are described in the attached Executive Severance Agreement that I previously entered into with Lands’ End, Inc., dated September 6, 2022 (the “Severance Agreement”), I, for myself, my heirs, administrators, representatives, executors, successors and assigns, do hereby release Lands’ End, Inc., its current and former agents, subsidiaries, affiliates, related organizations, employees, officers, directors, shareholders, attorneys, successors, and assigns (collectively, “Lands’ End”) from any and all claims of any kind whatsoever, whether known or unknown, arising out of, or connected with, my employment with Lands’ End and the termination of my employment. Without limiting the general application of the foregoing, this General Release and Waiver releases, to the fullest extent permitted under law, all contract, tort, defamation, and personal injury claims; all claims based on any legal restriction upon Lands’ End’s right to terminate my employment at will; Title VII of the Civil Rights Act of 1964, 42 U.S.C. §§ 2000e et seq.; the Age Discrimination in Employment Act, 29 U.S.C. §§ 621 et seq.; the Americans with Disabilities Act, 42 U.S.C. §§ 12101 et seq.; the Rehabilitation Act of 1973, 29 U.S.C. §§ 701 et seq.; the Employee Retirement Income Security Act of 1974, 29 U.S.C. §§ 1001 et seq. (“ERISA”); 29 U.S.C. § 1985; the Civil Rights Reconstruction Era Acts, 42 U.S.C. §§ 1981-1988; the National Labor Relations Act, 29 U.S.C. §§ 151 et seq.; the Family & Medical Leave Act, 29 U.S.C. §§ 2601 et seq.; the Immigration & Nationality Act, 8 U.S.C. §§ 1101 et seq.; Executive Order 11246 and all regulations thereunder; the Wisconsin Fair Employment Act, Wis. Stat. §§ 111.31-111.395; the Wisconsin Family & Medical Leave Act, Wis. Stat. § 103.10; the Wisconsin Worker’s Compensation Act, Wis. Stat. Ch. 102; and any and all other state, federal or local laws of any kind, whether administrative, regulatory, statutory or decisional.

This General Release and Waiver does not apply to any claims that may arise after the date I sign this General Release and Waiver. Also excluded from this General Release and Waiver are any claims that cannot be waived by law, including but not limited to (1) my right to file a charge with or participate in an investigation conducted by the Equal Employment Opportunity Commission and (2) my rights or claims to director and officer indemnification rights and any benefits accrued under benefit plans maintained by Lands’ End and governed by ERISA. I do, however, waive any right to any monetary or other relief flowing from any agency or third-party claims or charges, including any charge I might file with any federal, state or local agency. I warrant and represent that I have not filed any complaint, charge, or lawsuit against Lands’ End with any governmental agency or with any court. The release does not cover any rights to indemnification or rights to directors and officers liability insurance coverage, including under Section 12 of the Severance Agreement.

I also waive any right to become, and promise not to consent to become a participant, member, or named representative of any class in any case in which claims are asserted against Lands’ End that are related in any way to my employment or termination of employment at Lands’ End, and that involve

events that have occurred as of the date I sign this General Release and Waiver. If I, without my consent, am made a member of a class in any proceeding, I will opt out of the class at the first opportunity afforded to me after learning of my inclusion. In this regard, I agree that I will execute, without objection or delay, an “opt-out” form presented to me either by the court in which such proceeding is pending, by class counsel or by counsel for Lands’ End.

I have read this General Release and Waiver and understand all of its terms.

I have signed it voluntarily with full knowledge of its legal significance.

I have had the opportunity to seek, and I have been advised in writing of my right to seek, legal counsel prior to signing this General Release and Waiver.

I was given at least twenty-one (21) days to consider signing this General Release and Waiver. I agree that any modification of this General Release and Waiver Agreement will not restart the twenty-one (21)-day consideration period.

I understand that if I sign the General Release and Waiver, I can change my mind and revoke it within seven (7) days after signing it by notifying the General Counsel of Lands’ End in writing at Lands’ End, Inc., 5 Lands’ End Lane, Dodgeville, Wisconsin 53595. I understand the General Release and Waiver will not be effective until after the seven (7)-day revocation period has expired.

I understand that the delivery of the consideration herein stated does not constitute an admission of liability by Lands’ End and that Lands’ End expressly denies any wrongdoing or liability.

Exhibit B

SEVERANCE BENEFITS

You acknowledge and agree that the consideration referenced in this Section 2 represents the entirety of the amounts you are eligible to receive as severance pay and benefits from the Company.