Document:

EX-10.20

 Exhibit 10.20 

LANDS’ END, INC. 

ANNUAL INCENTIVE PLAN 

SECTION 1 
 GENERAL

 1.1. Purpose. The Lands’ End, Inc. Annual Incentive Plan (“AIP”) is a performance-based incentive
program. The purpose of the AIP is to reward eligible employees of Lands’ End, Inc. (“Company”) and its participating subsidiaries and affiliates (collectively referred to as “Employers”), for sustained Company fiscal
performance. Awards (as defined in Section 9) under the AIP are designed to vary commensurately with achieved performance. Both (a) Awards not structured to satisfy the requirements for “performance-based compensation” under
Section 162(m) of the Internal Revenue Code (“Code”), and (b) Section 162(m) Awards, which are structured to satisfy such requirements, may be issued under the AIP. The AIP is hereby effective as of the Effective Time as
defined in the Separation and Distribution Agreement by and between Sears Holdings Corporation (“Sears Holdings”) and the Company (“Effective Date”). For purposes of this document, the Effective Date shall also refer to the
effective date of an annual incentive plan established in the future by the Compensation Committee under the AIP. 
 1.2. Operation,
Administration and Definitions. The operation and administration of the AIP, including the Awards made under the AIP with respect to any Performance Period (as defined under subsection 3.3), shall be subject to the provisions of
Section 7. Capitalized terms in the AIP shall be defined in the provision in which a term first appears or as set forth in Section 9. The AIP is established under, and constitutes a part of, the Lands’ End, Inc. Umbrella Incentive
Program (“UIP”). 
 1.3. Participating Employers. Each Employer whose eligible employees are covered by the AIP may
be referred to herein as a “Participating Employer”. Participating Employers are listed on Appendix A. 
 SECTION 2

 PARTICIPATION 

2.1. Eligible Employee. Except as provided herein, “Eligible Employee” means as to any Performance Period an employee
of the Company or a participating Subsidiary who is designated by the Compensation Committee or Senior Corporate Compensation Executive as eligible to participate in an AIP as of such Performance Period. The Senior Corporate Compensation Executive
shall make eligibility determinations under this Section 2 with respect to all Eligible Employees other than those who are “Executives” for whom compensation matters are under the purview of the Compensation Committee (as defined in
Section 9), and the Compensation Committee shall make eligibility determinations with respect to all Executives. Once designated as eligible to participate, an Eligible Employee shall become a “Participant” in the applicable AIP;
provided, however, that an otherwise Eligible Employee shall not be a Participant in the AIP with respect to any portion of a Performance Period during which he or she is participating under any other annual incentive program that is sponsored by
the Company or any subsidiary or affiliate of the Company regardless of when awards under such program are paid. 

 Sears Holdings Corporation 

Annual Incentive Plan 
  

 2.2. New Hires; Changes in Status; Promotions and Demotions. 

(a) New Hires. The Compensation Committee, the Senior Corporate Compensation Executive, or an authorized
representative of either, as applicable, shall determine whether and when an employee who is a new hire is an Eligible Employee. The terms and conditions of any Award for such an individual shall be (i) based on the Target Annual Incentive for
the new hire’s incentive-eligible position and (ii) subject to a fraction, the numerator of which is the number of full days on active payroll (except as otherwise provided in Section 6.2) during the applicable Performance Period (as
defined in subsection 3.3) that the Eligible Employee was a Participant in the AIP and the denominator of which is the number of full days in such Performance Period. 

(b) Changes in Status. The Compensation Committee or Senior Corporate Compensation Executive, as applicable,
shall determine whether and when an employee who has a change in status becomes or ceases to be an Eligible Employee during the Performance Period. The terms and conditions of any Award for such an individual shall be (i) based on the Target
Annual Incentive for the incentive-eligible position and (ii) subject to a fraction, the numerator of which is the number of full days on active payroll (except as otherwise provided in Section 6.2) during the applicable Performance Period
that the Eligible Employee was a Participant in the AIP and the denominator of which is the number of full days in such Performance Period. 

(c) Promotion. If a Participant is promoted, the Award for such an individual shall be based on a pro-ration, whereby
the Target Annual Incentive for the new position will apply to the remainder of the applicable Performance Period and the Target Annual Incentive for the immediately preceding incentive-eligible position will apply to the portion of such Performance
Period immediately preceding the effective date of the promotion, subject to subsection 3.2. 
 (d) Demotions. If a
Participant is demoted, the Award for such an individual shall be based on a pro-ration, whereby the Target Annual Incentive for the new incentive-eligible position (if any) will apply only to the remainder of the Performance Period and the Target
Annual Incentive for the immediately preceding incentive-eligible position will apply only to the portion of the Performance Period immediately preceding the effective date of the demotion, subject to subsection 3.2. 

SECTION 3 
 ANNUAL
INCENTIVE AWARDS 
 3.1. Annual Incentive Awards. Except as provided herein, the Senior Corporate Compensation
Executive shall determine, in its sole discretion, the “Target Annual Incentive” (as defined herein) for each Participant. Notwithstanding the foregoing, the Compensation Committee shall approve the Target Annual Incentives and the Awards
for Executives (as defined in Section 9) under its purview. 
 (a) A “Target Annual Incentive” shall refer to
the percentage of a Participant’s rate of base pay during a Performance Period, which may be reflected as a percentage of base pay or flat dollar amount (or combination thereof). The Target Award Incentive shall consist of any annual, quarterly
and/or monthly award components applicable to a Participant. 

  
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 (b) The “Target Incentive Award” shall consist of a commitment by
the Company to distribute, at the time(s) specified in, and in accordance with the applicable provisions of, Section 5 below, a dollar amount based on a Participant’s Target Annual Incentive and based on actual performance of the Company
and the Participant, as compared to established performance goals described in Section 4 below, subject to subsection 4.1(b)(vii). The Target Incentive Award shall be subject to pro-ration (if applicable) and certification of the calculation of
the final Award amount by the Compensation Committee or Senior Corporate Compensation Executive, as applicable. A Participant’s Target Incentive Award may consist of annual, quarterly and/or monthly award components as described below in this
Section 3.1. 
 (c) The “Quarterly Incentive Award” shall refer to the final quarterly portion of a
Participant’s Target Incentive Award that is based on applicable quarterly performance goal(s) and measures, and, if any, may be payable on a Quarterly Payment Date (as defined in subsection 5.1(b) below) or the Annual Payment Date (as defined
in subsection 5.1(a) below), as determined by the Compensation Committee or Senior Corporate Compensation Executive, as applicable. Notwithstanding the foregoing, this does not preclude the Compensation Committee or Senior Corporate Compensation
Executive, as applicable, from creating a Performance Period by combining Fiscal Quarters (as defined in Section 9) months into a period less than a Fiscal Year. 

(d) The “Monthly Incentive Award” shall refer to the final monthly portion of a Participant’s Target Incentive
Award that is based on applicable monthly performance goal(s) and measures, and, if any, may be payable on a Monthly Payment Date (as defined in subsection 5.1(b) below) or the Annual Payment Date (as defined in subsection 5.1(a) below), as
determined by the Compensation Committee or Senior Corporate Compensation Executive, as applicable. Notwithstanding the foregoing, this does not preclude the Compensation Committee or Senior Corporate Compensation Executive, as applicable, from
creating a Performance Period by combining Fiscal Months (as defined in Section 9) into a period less than a Fiscal Year. 

(e) The “Annual Incentive Award” shall refer to the final annual portion of a Participant’s Target Incentive
Award payable on the Annual Payment Date, if any. 
 (f) Any Quarterly Incentive Award, Monthly Incentive Award and/or Annual
Incentive Award shall be satisfied by a distribution in accordance with Section 5 and subject to Sections 6 and 7. 
 3.2.
Adjustments based on Status Changes during Performance Period. Notwithstanding anything in the AIP to the contrary, with respect to Awards that are not Section 162(m) Awards, and prior to the settlement of any such Award, if the
Target Annual Incentive for a new incentive-eligible position (including if due to promotion or demotion) is lower or higher than the Target Annual Incentive for a Participant’s immediately prior position, the Participant’s Target
Incentive Award may be adjusted by the Compensation Committee or Senior Corporate Compensation Executive, as applicable, to ensure that the overall target cash compensation (i.e., the sum of base pay and Target Annual Incentive) for the new position
is comparable to the overall target cash compensation for the immediately prior position. 

  
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 3.3. Performance Period. The “Performance Period” refers to
(a) with respect to the portion of an Award that is payable based on the Fiscal Year (as defined in Section 9), the applicable Fiscal Year, (b) with respect to the portion of an Award that is payable based on a Fiscal Quarter (as
defined in Section 9), the applicable Fiscal Quarter, and (c) with respect to the portion of an Award that is payable based on a Fiscal Month (or months), the applicable calendar or Fiscal Month(s); in either case, as determined by the
Compensation Committee or Senior Corporate Compensation Executive, as applicable. The amount of an Award, if any, shall be determined following completion of the applicable Performance Period in accordance with this Section 3 and
Section 4. 
 3.4. Pro-ration. 

(a) The Annual Incentive Award and applicable Quarterly Incentive Awards and/or Monthly Incentive Awards, if any, of a
Participant who experiences a status change or position change are subject to pro-ration based on the number of days worked on active payroll in each incentive-eligible position during the applicable Performance Period. 

(b) The Annual Incentive Award and applicable Quarterly Incentive Awards and/or Monthly Incentive Awards, if any, of a
Participant who experiences a demotion, promotion, status or location change are subject to pro-ration based on the Target Annual Incentives in effect during the applicable Performance Period, subject to Sections 2.2 and 3.2 above. 

(c) The Annual Incentive Award and applicable Quarterly Incentive Awards and/or Monthly Incentive Awards, if any, of a
Participant who experiences a disability or death, as described in subsections 6.1(b) and (c) respectively, shall be pro-rated based upon a fraction, the numerator of which is the number of days worked on active payroll in an incentive-eligible
position during the applicable Performance Period and the denominator of which is the number of days in such Performance Period. 

(d) The Annual Incentive Award and applicable Quarterly Incentive Awards and/or Monthly Incentive Awards, if any, of a
Participant who experiences an unpaid leave of absence during the applicable Performance Period shall be pro-rated in accordance with subsection 6.2(a). 

3.5. Reimbursement of Excess Awards. If the Company’s financial statements or approved performance measures under the AIP
are the subject of a restatement due to error or misconduct, to the extent permitted by governing law, in all appropriate cases, the Company will seek reimbursement of Excess Awards paid under the AIP to Executives (and any other Participant who is
determined to have known of or been involved in any such misconduct) for the relevant performance period(s). For purposes of the AIP, an “Excess Award” means the positive difference, if any, between (a) the Annual Incentive
Award, Quarterly Incentive Awards and/or Monthly Incentive Award paid to an Executive and (b) the Annual Incentive Award, Quarterly Incentive Awards and/or Monthly Incentive Award that would have been paid to the Executive, had the Award been
calculated based on the Company’s financial statements or 

  
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performance measures as restated. The Company will not be required to award Participants, including Executives, an additional AIP payment should the restated financial statements or
performance measures result in a higher Annual Incentive Award, Quarterly Incentive Awards or Monthly Incentive Award. 
 SECTION 4

 GOALS AND PERFORMANCE 

4.1. Company Goals and Performance. For each Performance Period, the Compensation Committee or Senior Corporate Compensation
Executive, as applicable, shall establish in writing the performance goals and any particulars or components (including without limitation Targets or Thresholds) applicable to each business unit (including sub-business units) and, with respect to
each Participant, his or her Assignment (as defined in Section 9). The performance goals and any particulars or components will be objectively measurable and any payment based upon the achievement of a specified percentage or level of
performance. 
 (a) Goals. Except as otherwise approved by the Compensation Committee or Senior Corporate Compensation
Executive, as applicable, with respect to a Performance Period, the performance goals shall be based upon one or more of the performance measures identified in the UIP. 

(b) Performance. Except as otherwise approved by the Compensation Committee or Senior Corporate Compensation Executive,
as applicable, with respect to a Performance Period, the following concepts shall apply: 
 (i) Achievement of Target.
With respect to each Performance Period, the Compensation Committee or Senior Corporate Compensation Executive, as applicable, shall establish a target level of achievement for each performance goal (“Target”), which may be reflected as
annual, quarterly and/or monthly Targets, as applicable to the performance measure. If achieved, payout of applicable Award(s) to which that performance goal applies shall be at 100%, subject to any applicable modifiers or adjustments. 

(ii) Achievement of Threshold. With respect to each Performance Period, the Compensation Committee or Senior Corporate
Compensation Executive, as applicable, shall establish a threshold level of achievement that must be met with respect to a performance goal before any portion of an applicable Award to which the performance goal applies is payable
(“Threshold”), which may be reflected as annual, quarterly and/or monthly Thresholds. If achieved, payout of Awards to which that performance goal applies shall be at the Threshold percentage, subject to any applicable modifiers or
adjustments. 
 (iii) Achievement Between Threshold and Target. In the event achievement of a performance goal falls
between Threshold and Target with respect to a Performance Period, the Compensation Committee or Senior Corporate Compensation Executive, as applicable, may establish a formula for determining payout levels between these two points, which payout
shall be subject to any applicable modifiers or adjustments. 

  
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 (iv) Payout Above Target. In the event achievement of a performance
goal exceeds the Target with respect to a Performance Period, the Compensation Committee or Senior Corporate Compensation Executive, as applicable, may establish a formula for determining payout levels above Target, which payout shall be subject to
any applicable modifiers or adjustments. The Compensation Committee or Senior Corporate Compensation Executive, as applicable, also may provide for a maximum payout level or no maximum. 

(v) Modifiers. Notwithstanding this subsection 4.1, for each Performance Period, the Compensation Committee or Senior
Corporate Compensation Executive, as applicable, shall have the discretion to establish individual, team, department, store or other unit performance modifiers to an Annual Incentive Award, Quarterly Incentive Award or Monthly Incentive Award, which
enables the Award to be modified, positively (subject to subsection 4.2 below) or negatively, based on the performance of an individual, team, department, store or other unit with respect to a Performance Period. 

(vi) Qualifiers. Notwithstanding this subsection 4.1, for each Performance Period, the Compensation Committee or Senior
Corporate Compensation Executive, as applicable, shall have the discretion to establish qualifiers based on Company, business unit, store, department or other unit performance measures, which qualifiers would need to be achieved, in addition to
achievement of the performance goals described above, in order for any Annual Incentive Award, Quarterly Incentive Award or Monthly Incentive Award to be paid. Such qualifiers may or may not be (1) equivalent to specific AIP goals and
thresholds, and (2) the same for all Participants. 
 (vii) Discretionary Allocation. Notwithstanding this
subsection 4.1 or anything else in the AIP to the contrary, with respect to non-Executive Participants, for each Performance Period the Senior Corporate Compensation Executive shall have the discretion to establish that a portion of a
Participant’s Target Incentive Award shall be subject to a discretionary performance measure, based on relative contribution and overall productivity as determined in the sole discretion of the Company. 

4.2. Awards Subject to Code Section 162(m) 

(a) General Rules. 

(i) Notwithstanding anything in the AIP to the contrary, this Section 4.2 will apply to all Section 162(m) Awards. To
the extent there is a conflict between the rules of this Section 4.2 and any other section in the AIP, the terms of this Section 4.2 will control. 

(ii) In no event will positive discretion be applied, by the Compensation Committee or Senior Corporate Compensation Executive,
to any Section 162(m) Award with respect to the Performance Period or as of the Payment Date (as defined under subsection 5.1(c) below). Modifiers described in Section 4.1(b)(v) shall not apply to any Section 162(m) Award. 

(iii) To the extent that an Executive experiences a promotion or other change in status, no adjustment to a Section 162(m)
Award shall be made if such adjustment would not otherwise meet the requirements of Code Section 162(m). 

  
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 (b) Performance Measures. Section 162(m) Awards shall use the
performance measures established under the UIP. As provided in the UIP, at the time of establishing the performance goals, the Compensation Committee may exclude the effects of extraordinary items in a manner that satisfies the requirements of Code
Section 162(m). 
 (c) Establishment of Performance Goals. Section 162(m) Awards shall have the applicable
objective performance goals and any particulars or components established in writing and approved by the Compensation Committee by the deadline established in the UIP, in accordance with Code Section 162(m) and the regulations issued
thereunder. 
 (d) Attainment of Performance Goals. Distributions under Section 162(m) Awards shall not be made
until the Compensation Committee has determined, and certifies in writing, that the performance goals have been satisfied. 

(e) Maximum Award. Section 162(m) Awards are subject to the maximum award limits established under the UIP. 

4.3. Additional Requirements. All Annual Incentive Awards, Quarterly Incentive Awards and Monthly Incentive Awards awarded under
the AIP are subject to the provisions of Sections 5, 6 and 7. 
 SECTION 5 

DISTRIBUTION 
 5.1.
Time of Payment. Subject to Sections 6 and 7, the Annual Incentive Awards, Quarterly Incentive Awards and Monthly Incentive Awards that are payable under the AIP, based on the Awards and payout formulas described at Sections 3 and 4,
shall be distributed after the Compensation Committee or Senior Corporate Compensation Executive, as appropriate, has determined the amount to be paid to each Participant, subject to the following: 

(a) The Annual Incentive Award, if any, shall be distributed no later than the date that is the 15th day of the third month following the last day of the relevant Performance Period; provided, however, that no distribution shall be made hereunder until after the Compensation Committee has certified
the attainment of the performance goals and the Compensation Committee or Corporate Compensation, as appropriate, has determined the amount to be paid to each Participant. Notwithstanding anything herein to the contrary, such distributions shall be
made no later than required by Code Section 409A to avoid treatment of the AIP as a deferred compensation plan under Code Section 409A. The date as of which payment of an Annual Incentive Award is made in accordance with this subsection
5.1(a) shall be the “Annual Payment Date.” 

  
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 (b) The Quarterly Incentive Awards, if any, shall be distributed, as follows:

 (i) If payable quarterly, then with respect to the first three Fiscal Quarters of the Performance Period, within sixty
(60) days of the close of the applicable Fiscal Quarter (or quarters if combined as a Performance Period within the applicable Fiscal Year) (or as soon as administratively feasible thereafter if later), and with respect to the fourth Fiscal
Quarter of the Performance Period, no later than the date that is the 15th day of the third month following the last day of the applicable fourth Fiscal Quarter; which may be referred to as a
“Quarterly Payment Date”; 
 (ii) If payable annually, no later than the date that is the 15th day of the third month following the last day of the applicable Fiscal Year that constitutes the Performance Period; and 

(iii) Provided, however, that no distribution shall be made hereunder until after the Compensation Committee or Corporate
Compensation, as appropriate, has certified the attainment of the performance goals and the Compensation Committee or Corporate Compensation, as appropriate, has determined the amount to be paid to each Participant. 

(c) The Monthly Incentive Awards, if any, shall be distributed, as follows: 

(i) If payable monthly, then with respect to the first eleven Fiscal Months of the Performance Period, within thirty
(30) days of the close of the applicable Fiscal Month (or months if combined as a Performance Period within the applicable Fiscal Year) (or as soon as administratively feasible thereafter if later), and with respect to the twelve Fiscal Month
of the Performance Period, no later than the date that is the 15th day of the third month following the last day of the applicable twelfth Fiscal Month, which may be referred to as a “Monthly
Payment Date”; 
 (ii) If payable annually, no later than the date that is the 15th day of the third month following the last day of the applicable Fiscal Year that constitutes the Performance Period; and 

(iii) Provided, however, that no distribution shall be made hereunder until after the Compensation Committee or Corporate
Compensation, as appropriate, has certified the attainment of the performance goals and the Compensation Committee or Corporate Compensation, as appropriate, has determined the amount to be paid to each Participant. 

(d) The Annual Payment Date, Quarterly Payment Date and Monthly Payment Date may be referred to herein generically the
“Payment Date”. 
 5.2. Form of Payment. An Annual Incentive Award, Quarterly Incentive Awards and Monthly Incentive
Awards shall generally be satisfied by a single, lump sum cash payment to the Participant with respect to the applicable Performance Period; provided, however, that, at the discretion of the Compensation Committee, the Company may elect, by such
deadline as specified under uniform and nondiscriminatory rules established by the Compensation Committee, to satisfy such Award by payment of shares of Company common stock (“Stock”) in 

  
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lieu of cash, or a combination of cash and shares of Stock. The number of shares of Stock shall be equal to (a) the amount of the Award to be paid in stock in accordance with this subsection
5.2, divided by (b) the fair market value of a share of Stock as evidenced by its closing price, on the principal securities exchange or market on which the Stock is then listed or admitted, on the business day immediately preceding the date of
distribution or, if the Stock is not traded on that date, on the next preceding date on which Stock was traded; provided that issuance of any shares of Stock in accordance with this subsection 5.2 shall be contingent on the availability of shares of
Stock under any shareholder-approved plan of the Company providing for the issuance of Stock in satisfaction of the Awards hereunder (which in no event shall be an employee stock purchase plan). 

SECTION 6 

TERMINATION OF EMPLOYMENT; LEAVE OF ABSENCE; REINSTATEMENT 

Any Award payable under this Section 6 shall be payable in accordance with Section 5. 

6.1. Termination of Employment. If a Participant incurs a termination of employment before the applicable Payment Date (as
defined in Section 5.1(c) above) for a Performance Period, the effect of termination of employment on a Participant’s right to receive an Award under the AIP shall depend on the reason for the termination, as described in this subsection
6.1. 
 (a) Voluntary Termination or Involuntary Termination. In the event that prior to the Payment Date of an Award,
a Participant (i) voluntarily terminates employment (for any reason other than due to permanent and total disability (as defined in subsection (b) immediately below)) or (ii) is involuntarily terminated for any reason (other than
death), such Participant shall forfeit his or her Award, except as prohibited by law. A Participant’s decision to retire prior to the Payment Date of an Award is a voluntary termination and such Participant shall forfeit his or her Award. 

(b) Disability. Except as otherwise approved by the Compensation Committee or Senior Corporate Compensation
Executive, as applicable, in the event that prior to the Payment Date of an Award, a Participant suffers a permanent and total disability (as defined in the Company’s long-term disability program, regardless of whether the Participant is
covered by such program) while employed by the Company or an Employer resulting in termination or retirement, subject to Section 7 below, such Participant shall be entitled to a distribution of the Award that would otherwise be payable to the
Participant under Sections 3 and 4 above, pro-rated based upon a fraction, the numerator of which is the number of full days worked on active payroll in an incentive-eligible position during the applicable Performance Period and the denominator of
which is the number of days in such Performance Period (or the number of days remaining in such Performance Period after the individual is assigned to an incentive-eligible position). 

(c) Death. Except as otherwise approved by the Compensation Committee or Senior Corporate Compensation Executive, as
applicable, in the event that a Participant dies while employed by a Participating Employer but prior to the Payment Date of his or her Award, the estate of such Participant shall be entitled to a distribution of the Award, if any, payable in cash
that would otherwise be payable to the Participant under Sections 3 and 4 above, pro-rated based upon a fraction, the numerator of which 

  
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is the number of full days worked on active payroll in an incentive-eligible position during the applicable Performance Period and the denominator of which is the number of full days in such
Performance Period (or the number of days remaining in such Performance Period after the individual is assigned to an incentive-eligible position). 

6.2. Leave of Absence.  

(a) General. Except as otherwise approved by the Compensation Committee or Senior Corporate Compensation Executive, as
applicable, in the event that a Participant is on an unpaid leave of absence any time during the Performance Period or at the time of the Payment Date, subject to subsections (b) and (c) immediately below and Section 7, such
Participant shall be entitled to a distribution of the Award that would otherwise be payable to the Participant under Sections 3 and 4 above, pro-rated based upon a fraction, the numerator of which is the number of full days worked on active payroll
in an incentive-eligible position during the applicable Performance Period and the denominator of which is the number of days in such Performance Period. 

(b) Short-Term Disability. Subject to subsection 6.2(a) above, in the event that a Participant is on a leave of absence
due to short-term disability (including, for purposes of the AIP, paid maternity leave) any time during the Performance Period, subject to subsection (c) below and Section 7, the period of the leave of absence shall be treated as time on
active payroll and will be credited toward the determination of the Participant’s Award and the Participant shall be entitled to payment of the Award in accordance with Section 5, even if the Participant is on the short-term disability
leave of absence as of the Payment Date. 
 (c) Salary Continuation. In the event that a Participant is receiving
salary continuation under a severance-related agreement or a Company-sponsored transition pay or severance pay plan as of the Payment Date, such Participant shall forfeit his or her Award. 

6.3. Reinstatement. If a Participant who forfeited his or her Award with respect to a Performance Period as a result of a
termination of employment is reinstated or rehired during the Performance Period, any Award attributable to the portion of such Performance Period prior to the termination of employment shall remain forfeited. Notwithstanding the foregoing, such a
Participant shall be eligible for an Award based on a fraction, the numerator of which is the number of days worked on active payroll in an incentive-eligible position on or after the date of reinstatement or rehire during the Performance Period and
the denominator of which is the number of days in such Performance Period. 
 SECTION 7 

OPERATION AND ADMINISTRATION 

7.1. Compensation Committee and Senior Corporate Compensation Executive. 

(a) Compensation Committee. Notwithstanding subsection (b) immediately below, the Compensation Committee:

 (i) Shall approve the Target Annual Incentives and the Awards, including eligibility for Quarterly Incentive Awards, for
Executives under its purview; 

  
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 (ii) With respect to Executives under its purview, shall have the authority
and discretion to establish the terms, conditions, restrictions, and other provisions of such Awards, including without limitation the performance goals and the performance measures for each such Executive’s Assignment in accordance with
Section 4, and to amend, cancel, or suspend Awards (in accordance with Section 8), subject to the requirements of Code Section 162(m), if applicable; 

(iii) May make additional changes to the AIP that it deems appropriate for the effective administration of the AIP; provided
however, that these changes may not increase the benefits to which Participants may become entitled under the AIP nor change the pre-established measures or goals that have been approved, except as explicitly provided in the AIP; and 

(iv) Shall be responsible for all other duties and responsibilities allocated to the Compensation Committee under the terms and
conditions of the AIP. 
 (b) Senior Corporate Compensation Executive. Except as provided in subsection
(a) immediately above, the Senior Corporate Compensation Executive: 
 (i) Shall Determine the Target Annual Incentive
and Awards, including eligibility for Quarterly Incentive Awards and Monthly Incentive Awards, for Participants other than Executives under the purview of the Compensation Committee; 

(ii) Shall have the authority to control and manage the operation and administration of the AIP; 

(iii) Shall be responsible for the day-to-day administration of the AIP, including without limitation the exception process
described in Section 7.2 below; 
 (iv) With respect to Participants other than Executives under the purview of the
Compensation Committee and subject to the other provisions of the AIP, shall have the authority and discretion to determine the time or times of receipt of Awards, to establish the terms, conditions, restrictions, and other provisions of such
Awards, and to amend, cancel, or suspend Awards (in accordance with Section 8), subject to the requirements of Code Section 162(m), if applicable; and 

(v) Shall be responsible for all other duties and responsibilities allocated to the Senior Corporate Compensation Executive
under the terms and conditions of the AIP. 

  
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 (c) Any determinations by the Compensation Committee or Senior Corporate
Compensation Executive, as applicable, regarding this AIP are binding on all applicable Participants. 
 (d) The Compensation
Committee and the Senior Corporate Compensation Executive, as appropriate, shall have the authority and discretion to interpret the AIP, to establish, amend, and rescind any rules and regulations relating to the AIP and to make all other
determinations that may be necessary or advisable for the administration of the AIP. 
 7.2. Incentive Exceptions. The Senior
Corporate Compensation Executive shall have the authority to receive and consider requests by business units of the Participating Employers for an exception to an established performance measure due to circumstances outside of the business
unit’s control. The Senior Corporate Compensation Executive may establish a procedure for reviewing and approving or rejecting an exception. Any exception determination shall be binding. 

7.3. Discretion. Notwithstanding Section 7.2 or anything in the AIP to the contrary, with respect to Awards that are not
Section 162(m) Awards, and prior to the settlement of any such Award, the Compensation Committee or Senior Corporate Compensation Executive, as applicable, may change the pre-established measures and goals that have been approved for such Award
and increase or reduce the amount of such Award. 
 7.4. Tax Withholding. All distributions under the AIP are subject to
withholding of all applicable taxes. In the case of Awards under the AIP that are settled in shares of Stock, if any, the Compensation Committee or Senior Corporate Compensation Executive, as applicable, may condition the delivery of any shares or
other benefits under the AIP on satisfaction of the applicable withholding obligations. To the extent permitted by the Compensation Committee or Senior Corporate Compensation Executive, as applicable, such withholding obligations may be satisfied:
(a) through cash payment by the Participant; (b) through the surrender of shares of Stock which the Participant already owns (provided, however, that to the extent shares described in this subsection (b) are used to satisfy more than
the minimum statutory withholding obligation, as described below, then, except as otherwise provided by the Compensation Committee or Senior Corporate Compensation Executive, as applicable, payments made with shares of Stock in accordance with this
subsection (b) shall be limited to shares held by the Participant for not less than six months prior to the Payment Date (or such other period of time as the Company’s accountants may require)); or (c) through the surrender of shares
of Stock to which the Participant is otherwise entitled under the AIP; provided, however, that such shares under this subsection (c) may be used to satisfy not more than the Company’s minimum statutory withholding obligation (based on
minimum statutory withholding rates for Federal and state tax purposes, including payroll taxes, that are applicable to such supplemental taxable income). 

7.5. Source of Awards. In the case of Awards under the AIP that are settled in shares of Stock, such shares shall be distributed
under a stock plan adopted by the Company and approved by the shareholders thereof that provides for the issuance of Stock in satisfaction of Awards hereunder (which in no event shall be an employee stock purchase plan). In the event of any conflict
between this document and such stock plan, the provisions of the stock plan shall govern. 

  
 12 

 Sears Holdings Corporation 

Annual Incentive Plan 
  

 7.6. Settlement of Awards. The obligation to make payments and distributions
with respect to Awards may be satisfied through cash payments, the delivery of shares of Stock, or a combination thereof, as provided under subsection 5.2, subject, in the case of settlement in shares, to the terms of the stock plan under which the
Stock is issued. Satisfaction of any such obligations under an Award, which is sometimes referred to as the “settlement” of the Award, may be subject to such conditions, restrictions and contingencies as the Compensation Committee or
Senior Corporate Compensation Executive, as appropriate, shall determine. Each Employer shall be liable for payment of an Award due under the AIP with respect to any Participant to the extent that such benefits are attributable to the services
rendered for that Employer by the Participant. Any disputes relating to liability of an Employer for payment of an Award shall be resolved by the Compensation Committee or Senior Corporate Compensation Executive, as appropriate. 

7.7. Transferability. Except as otherwise provided by the Senior Corporate Compensation Executive, Awards under the AIP are not
transferable except as designated by the Participant by will or by the laws of descent and distribution. 
 7.8. Form and Time of
Elections. Unless otherwise specified herein, any election required or permitted to be made by any Participant or other person entitled to benefits under the AIP, and any permitted modification, or revocation thereof, shall be in
writing filed with the Senior Corporate Compensation Executive at such times, in such form, and subject to such restrictions and limitations, not inconsistent with the terms of the AIP, as the Senior Corporate Compensation Executive shall require.

 7.9. Action by Company or Employer. Any action required or permitted to be taken under the AIP by the Company or any other
Employer shall be by resolution of its board of directors, or by action of one or more members of the board of directors of such company (including a committee of the board) who are duly authorized to act for such board with respect to the
applicable action, or (except to the extent prohibited by applicable law or applicable rules of any securities exchange or similar entity) by a duly authorized officer of such company. 

7.10. Gender and Number. Where the context admits, words in any gender shall include any other gender, words in the singular
shall include the plural and the plural shall include the singular. 
 7.11. Limitation of Implied Rights. 

(a) Neither a Participant nor any other person shall, by reason of participation in the AIP, acquire any right in or title to
any assets, funds or property of the Company or any Employer whatsoever, including, without limitation, any specific funds, assets, or other property which the Company or any Employer, in its sole discretion, may set aside in anticipation of a
liability under the AIP. A Participant shall have only a contractual right to the cash, if any, payable under the AIP, unsecured by any assets of the Company or any Employer, and nothing contained in the AIP shall constitute a guarantee that the
assets of the Company or any Employer shall be sufficient to pay any benefits to any person. 
 (b) The AIP does not
constitute a contract of employment, and status as a Participant shall not give any Eligible Employee the right to be retained in the employ 

  
 13 

 Sears Holdings Corporation 

Annual Incentive Plan 
  

 
of the Company or any Employer, nor any right or claim to any benefit under the AIP, unless such right or claim has specifically accrued and vested under the terms of the AIP. 

7.12. Evidence. Evidence required of anyone under the AIP may be by certificate, affidavit, document or other information, which
the person charged with acting on such evidence considers pertinent and reliable, and which has been signed, made or presented by the proper party or parties. 

7.13. Information to be Furnished. The Company and the Participating Employers shall furnish the Compensation Committee and the
Senior Corporate Compensation Executive with such data and information as it determines may be required for it to discharge its duties. The records of the Company and the Participating Employers as to an employee’s or Participant’s
employment, termination of employment, leave of absence, reemployment, and compensation shall be conclusive on all persons unless determined to be incorrect. Participants and other persons entitled to benefits under the AIP must furnish the
Compensation Committee or Senior Corporate Compensation Executive, as appropriate, such evidence, data or information as the Compensation Committee or Senior Corporate Compensation Executive considers desirable to carry out the terms of the AIP,
subject to any applicable privacy laws. 
 7.14. Governing Law. The AIP will be governed under the internal laws of the state
of Illinois without regard to principles of conflicts of laws. The state and federal courts located in the state of Illinois shall have exclusive jurisdiction in any action, lawsuit or proceeding based on or arising out of the AIP. 

7.15. Severability. If any provision(s) of the AIP shall be found invalid, illegal, or unenforceable, in whole or in part, then
such provision(s) shall be modified or restricted so as to effectuate as nearly as possible in a valid and enforceable way the provisions hereof, or shall be deemed excised from the AIP, as the case may require, and the AIP shall be construed and
enforced to the maximum extent permitted by law, as if such provision(s) had been originally incorporated herein as so modified or restricted or as if such provision(s) had not been originally incorporated herein, as the case may be. 

SECTION 8 
 AMENDMENT
AND TERMINATION 
 The Company may amend or terminate the AIP at any time and for any reason in its sole discretion. No amendment
shall be made that would cause the AIP not to comply with any applicable law or rule of any applicable securities exchange or similar entity, or cause Participants to experience adverse tax consequences under Code Section 409A. The AIP and any
Award thereunder may be amended without Participant consent to the extent that the Compensation Committee (or its authorized representative) determines such amendment necessary to cause the AIP or any Award to comply with any applicable law or rule
of any applicable securities exchange or similar entity or to prevent adverse tax consequences under Code Section 409A for Participants. 

  
 14 

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Annual Incentive Plan 
  

 SECTION 9 

DEFINED TERMS 
 9.1.
Each capitalized term in the AIP is defined where it first appears herein or in this Section 9. In addition to the terms defined previously in the AIP, the following definitions shall apply: 

(a) Assignment. The term “Assignment” refers to the performance goals and measure(s) that have been assigned
by the Compensation Committee or Senior Corporate Compensation Executive, as appropriate, to a Participant, based upon position, location and/or business unit. Assignment also includes the weight of each performance measure assigned to the
Participant. 
 (b) Award. The term “Award” or “Awards” refers to any Annual Incentive Award(s),
Quarterly Incentive Award(s) and Monthly Incentive Award(s), as applicable, awarded under the AIP. 
 (c) Compensation
Committee. The term “Compensation Committee” refers to the Compensation Committee of the Board of Directors of Sears Holdings Corporation. 

(d) Code. The term “Code” means the Internal Revenue Code of 1986, as amended from time to time (and the
regulations issued thereunder). A reference to any provision of the Code shall include reference to any successor provision of the Code (and the regulations issued thereunder). 

(e) Executive. The term “Executive” refers to any employee of an Employer who holds a position of senior vice
president or higher of Sears Holdings Corporation (not of any subsidiary or affiliate) or any employee who is an officer under Section 16(b) of the Securities and Exchange Act of 1934 with respect to Sears Holdings Corporation. 

(f) Fiscal Month. The capitalized term “Fiscal Month” refers to a fiscal month within the applicable Fiscal
Year of the Company. 
 (g) Fiscal Quarter. The capitalized term “Fiscal Quarter” refers to a fiscal quarter
within the applicable Fiscal Year of the Company. 
 (h) Fiscal Year. The capitalized term “Fiscal Year”
refers to the applicable fiscal year of the Company. 
 (i) Section 162(m) Award. The term “Section 162(m)
Award” refers to any Award that is designated by the Compensation Committee as intended to meet the requirements for “performance-based compensation” under Code Section 162(m). 

(j) Senior Corporate Compensation Executive. The term “Senior Corporate Compensation Executive” refers to the
Senior Vice President and President, Talent and Human Capital Services (or equivalent), or if he or she has explicitly delegated his or her duties with respect to the AIP, as provided herein, then the Senior Corporate Compensation Executive shall
refer to such authorized representative to whom the duties of administering the AIP have been delegated. 

  
 15 

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Annual Incentive Plan 
  

 SECTION 10 

EXPIRATION OF AIP 

The payment obligation under the AIP with respect to a specific Performance Period shall expire, subject to earlier termination pursuant to
Section 8, on the date on which all Annual Incentive Awards, Quarterly Incentive Awards and/or Monthly Incentive Awards (if any) are paid in full or would have been payable in accordance with the provisions of the AIP with respect to such
Performance Period. Notwithstanding this Section 10, the Company’s right to reimbursement under Section 3.5 will continue to survive after the expiration of the AIP. 

  
 16EX-10.21

 Exhibit 10.21 

LANDS’ END, INC. 

LONG-TERM INCENTIVE PROGRAM 

SECTION 1 
 GENERAL

 1.1. Purpose. The Lands’ End, Inc. Long-Term Incentive Program (“LTIP”) is a performance-based
program. The LTIP is designed to motivate the executive leadership of Lands’ End, Inc. (“Company”) and the participating Subsidiaries (as defined in Section 8) to achieve significant, lasting change that successfully positions
the Company for future growth. Performance goals under the LTIP align Participants’ financial incentives with the financial goals of the Company. Awards (as defined in Section 8) under the LTIP are designed to vary commensurately with
achieved performance. Both (a) Awards not structured to satisfy the requirements for “performance-based compensation” under Section 162(m) of the Code, and (b) Section 162(m) Awards, which are structured to satisfy such
requirements, may be issued under the LTIP. The AIP is hereby effective as of the Effective Time as defined in the Separation and Distribution Agreement by and between Sears Holdings Corporation (“Sears Holdings”) and the Company
(“Effective Date”). For purposes of this document, the Effective Date shall also refer to the effective date of a long-term incentive program established in the future by the Compensation Committee under the LTIP. 

1.2. Operation, Administration, and Definitions. The operation and administration of the LTIP, including the Awards made under
the LTIP, shall be subject to the provisions of Section 6 (relating to operation and administration). Capitalized terms in the LTIP shall be defined as set forth in the LTIP (including as defined in Section 8). The LTIP is established
under, and constitutes a part of, the Lands’ End, Inc. Umbrella Incentive Program (“UIP”). 
 SECTION 2 

PARTICIPATION 
 2.1.
Eligible Employee. Except as provided herein, “Eligible Employee” means as to any Performance Period an employee of the Company or a participating Subsidiary, who is designated by the Compensation Committee or Senior
Corporate Compensation Executive as eligible to participate in an LTIP as of such Performance Period. The Senior Corporate Compensation Executive shall make eligibility determinations under this Section 2 with respect to all Eligible Employees
other than those who are Executives for whom compensation matters are under the purview of the Compensation Committee (as defined in Section 8), and the Compensation Committee shall make eligibility determinations with respect to all
Executives. Once designated as eligible to participant, an Eligible Employee shall become a “Participant” in the applicable LTIP. 

2.2. New Hires and Promotions to Eligible Employee Status. The Compensation Committee or Senior Corporate Compensation
Executive, as applicable, may designate as Participants those employees whom the Compensation Committee or Senior Corporate Compensation Executive, as applicable, determines have been newly hired or promoted into the group of Eligible Employees
identified in subsection 2.1 above. The Award of any Participant who was hired or promoted after the first day of the Performance Period (as described in subsection 3.2) shall be subject to a fraction, the numerator of which is the number of full
days remaining in the Performance Period beginning with the Participant’s date of hire or promotion, as applicable, and the denominator is the number of full days in the Performance Period. 

 Lands’ End, Inc. 

Long-Term Incentive Program 
  

 2.3. Demotions from Eligible Employee Status. If a Participant is demoted below
a position of divisional vice president (or equivalent), as of the date of such demotion, the individual will no longer be a Participant, will be deemed to have forfeited any unvested portion of his or her Award, and will receive no LTIP
distribution under Section 4. 
 2.4. Other Changes in Status 

(a) If a Participant is promoted or transferred after the Effective Date of the LTIP for a particular Performance Period, the
Compensation Committee or Senior Corporate Compensation Executive, as applicable, may make a second Target Incentive Award (as defined in subsection 3.1) to such individual and the total amount payable to such individual shall be based on a
pro-ration, whereby the Target Incentive Award for the new position will apply to the remainder of the Performance Period and the Target Incentive Award for the immediately preceding long-term incentive-eligible position, if applicable, will apply
to the portion of the Performance Period immediately preceding the effective date of the promotion. 
 (b) If a Participant
is demoted after the Effective Date of the LTIP for a particular Performance Period, but is still an Eligible Employee, the Compensation Committee or Senior Corporate Compensation Executive, as applicable, may make a second Target Incentive Award to
such individual and the total Award for such an individual shall be based on a pro-ration, whereby the Target Incentive Award for the new position will apply only to the remainder of the Performance Period and the Target Incentive Award for the
immediately preceding position will apply only to the portion of the Performance Period immediately preceding the effective date of the demotion, and in either case an Award will only be paid if the Target for the full Performance Period is met.

 SECTION 3 
 LTIP
INCENTIVE AWARDS 
 3.1. Target Incentive Awards. As of and after the applicable Effective Date, the Compensation
Committee or Senior Corporate Compensation Executive, as applicable, may award “Target Incentive Awards” (as defined in subsection 3.1(a) below) to each Participant designated by the Compensation Committee or Senior Corporate Compensation
Executive, as applicable, in an amount determined by the applicable entity in its sole discretion. In connection with such Awards, the Compensation Committee or Senior Corporate Compensation Executive, as applicable, shall establish a
“Target” and “Threshold”, as well as applicable award levels at the Target and Threshold achievement levels, under each objective performance goal or plan established under subsection 3.3 below; provided, however, that Threshold
shall be expressed as a percentage of Target. The Senior Corporate Compensation Executive shall make the determinations referred to in this Section 3 with respect to all Participants other than those who are Executives for whom compensation
matters are under the purview of the Compensation Committee. 

  
 2 

 Lands’ End, Inc. 

Long-Term Incentive Program 
  

 (a) A Target Incentive Award shall, at the date of grant, consist of a
commitment by the Company to distribute, at the time specified in, and in accordance with the provisions of, Section 4 below, a designated amount based on a target level of performance. 

(b) An “LTIP Incentive Award” refers to a percentage of a Participant’s Target Incentive Award payable on the
payment date (as defined in subsection 4.1 below), if any, based on the actual performance relative to the objective performance goals during the Performance Period, subject to approval of the final award amount by the Compensation Committee or
Senior Corporate Compensation Executive, as applicable, and to the provisions of subsection 6.4 
 3.2. Performance Period.
The “Performance Period” refers to the applicable Fiscal Years (as defined in Section 8) as determined by the Compensation Committee with respect to which an Award may be granted under the LTIP. The Compensation Committee shall
determine the Fiscal Years that shall constitute the Performance Period for each long-term incentive program established under the LTIP; provided that, in the case of an employee who is newly hired or promoted into the group of Eligible Employees
after the Effective Date, the Performance Period shall be such shorter period as established by the Compensation Committee or Senior Corporate Compensation Executive, if applicable. The amount of the LTIP Incentive Award shall be determined at the
completion of the Performance Period in accordance with subsection 3.1 above and subsection 4.1 below. 
 3.3. Financial Goals and
Performance. For each Performance Period, the Compensation Committee or Senior Corporate Compensation Executive shall establish in writing one or more performance plans that includes one or more objective performance goals and the required
levels of performance as described in this Section 3.3. The Compensation Committee or Senior Corporate Compensation Executive, as applicable, shall determine the level of performance for each performance plan, the performance plan to apply to
each business unit, and which performance plan applies to each Participant. 
 (a) Goals. Except as otherwise approved
by the Compensation Committee or Senior Corporate Compensation Executive, as applicable, with respect to a Performance Period, the performance goals shall be based upon one or more of the performance measures identified in the UIP. 

(b) Performance. Except as otherwise approved by the Compensation Committee or Senior Corporate Compensation Executive,
as applicable, with respect to a Performance Period, the following concepts shall apply: 
 (i) Achievement of Target.
With respect to each Performance Period, the Compensation Committee or Senior Corporate Compensation Executive, as applicable, shall establish a target level of achievement for each performance goal (“Target”). If achieved, payout of
Awards to which that performance goal applies shall be at 100%. 
 (ii) Achievement of Threshold. With respect to each
Performance Period, the Compensation Committee or Senior Corporate Compensation Executive, as applicable, shall establish a threshold level of achievement that 

  
 3 

 Lands’ End, Inc. 

Long-Term Incentive Program 
  

 
must be met with respect to a performance goal before any portion of an Award to which the performance goal applies is payable (“Threshold”). If achieved, payout of Awards to which that
performance goal applies shall be at a specified percentage established in writing at the same time and manner as the Threshold achievement level is established. 

(iii) Achievement Between Threshold and Target. In the event achievement of a performance goal falls between Threshold
and Target with respect to a Performance Period, the Compensation Committee or Senior Corporate Compensation Executive, as applicable, may establish a formula for determining payout levels between these two points in writing at the same time and
manner as the achievement levels are established. 
 (iv) Payout Above Target. In the event achievement of a
performance goal exceeds the Target with respect to a Performance Period, the Compensation Committee or Senior Corporate Compensation Executive, as applicable, may establish a formula for determining payout levels above Target in writing at the same
time and manner as the Target achievement level is established. The Compensation Committee or Senior Corporate Compensation Executive, as applicable, also may provide for a maximum payout level or no maximum. 

3.4. Awards Subject to Code Section 162(m). 

(a) General Rules. 

(i) Notwithstanding anything in the LTIP to the contrary, this subsection 3.4 will apply to all Section 162(m) Awards. To
the extent there is a conflict between the rules of this subsection 3.4 and any other section in the LTIP, the terms of this subsection 3.4 will control. 

(ii) In no event will positive discretion be applied, by the Compensation Committee or Senior Corporate Compensation Executive,
to any Section 162(m) Award with respect to a Performance Period or as of the payment date (as defined under subsection 4.1). 

(iii) To the extent that an Executive experiences a promotion or other change in status, no adjustment to a Section 162(m)
Award shall be made if such adjustment would not otherwise meet the requirements of Code Section 162(m). 
 (b)
Performance Measures. Section 162(m) Awards shall use the performance measures established under the UIP. As provided in the UIP, at the time of establishing the performance goals, the Compensation Committee may exclude the effects of
extraordinary items in a manner that satisfies the requirements of Code Section 162(m). 
 (c) Establishment of
Performance Goals. Section 162(m) Awards shall have the applicable objective performance goals and any particulars or components established in writing and approved by the Compensation Committee by the deadline established in the UIP in
accordance with Code Section 162(m). 
 (d) Attainment of Performance Goals. Distributions under
Section 162(m) Awards shall not be made until the Compensation Committee has determined, and certifies in writing, that the performance goals have been satisfied. 

  
 4 

 Lands’ End, Inc. 

Long-Term Incentive Program 
  

 3.5. Limitation on Individual Awards. Notwithstanding anything herein to the
contrary, the total LTIP Incentive Award paid to any Participant for a Performance Period pursuant to the LTIP shall in no event exceed $20 million. 

3.6. Additional Requirements. All LTIP Incentive Awards awarded under the LTIP (and any Stock, as defined in Section 4.2,
or cash otherwise distributable pursuant thereto) are subject to the provisions of Sections 4, 5 and 6. 
 3.7. Reimbursement of
Excess Awards. If Company’s financial statements or approved performance measures under the LTIP are the subject of a restatement due to error or misconduct, to the extent permitted by governing law, in all appropriate cases, the
Company will seek reimbursement of Excess Awards paid under the LTIP to Executives (and any other Participant who is determined to have known of or been involved in any such misconduct) for the relevant performance period(s). For purposes of
the LTIP, an “Excess Award” means the positive difference, if any, between (a) the LTIP Incentive Award paid to an Executive and (b) the LTIP Incentive Award that would have been paid to the Executive, had the Award been
calculated based on the Company’s financial statements or performance measures as restated. The Company will not be required to award Participants, including Executives, an additional LTIP payment should the restated financial statements
or performance measures result in a higher LTIP Incentive Award. 
 SECTION 4 

DISTRIBUTION 
 4.1.
Time of Payment. Subject to Sections 5 and 6, the cash or shares of Stock, if any, that result from the payout formula described at Section 3 shall be distributed, in a single lump sum, as soon as practicable after the
Compensation Committee or Senior Corporate Compensation Executive, as appropriate has determined and approved the amount to be paid to each Participant, which shall in no event be later than the date that is the 15th day of the third month following the last day of the relevant Performance Period. Notwithstanding anything herein to the contrary, such distributions shall be made no later than required by Code
Section 409A to avoid treatment of the LTIP as a deferred compensation plan under Code Section 409A. The date as of which payment is made in accordance with this subsection 4.1 is referred to herein as the “payment date.” 

4.2. Form of Payment. An LTIP Incentive Award shall generally be satisfied by a distribution in cash to the Participant,
provided, however, that, at the discretion of the Compensation Committee, the Company may elect, by such deadline as specified under uniform and nondiscriminatory rules established by the Compensation Committee, to satisfy such LTIP Incentive Award
by payment of shares of Company common stock (“Stock”) in lieu of cash, or a combination of cash and shares of Stock. The number of shares of Stock shall be equal to (i) the amount of the Award to be paid in stock in accordance with
this subsection 4.2, divided by (ii) the fair market value of a share of Stock as evidenced by its closing price, on the principal securities exchange or market on which the shares are then listed or admitted, on the business day immediately
preceding the date of distribution or, if the Stock is not traded on that date, on 

  
 5 

 Lands’ End, Inc. 

Long-Term Incentive Program 
  

 
the next preceding date on which Stock was traded; provided that issuance of any shares of Stock in accordance with this subsection 4.2 shall be contingent on the availability of shares of Stock
under any shareholder-approved plan of the Company providing for the issuance of Stock in satisfaction of the Awards hereunder (which in no event shall be an employee stock purchase plan). 

SECTION 5 

TERMINATION OF EMPLOYMENT 

The effect of termination of employment on a Participant’s right to receive a LTIP Incentive Award (whether payable in cash or Stock)
depends on the reason for the termination, as described below. 
 5.1. Termination of Employment. 

(a) Voluntary Termination or Involuntary Termination. In the event that a Participant (i) voluntarily terminates
employment (for any reason other than due to permanent and total disability, as defined in the Company’s long-term disability program, regardless of whether the Participant is covered by such program) or (ii) is involuntarily terminated
for any reason (other than death) prior to the payment date (as defined in subsection 4.1 above) of his or her Award, such Participant shall forfeit all of his or her Award. 

(b) Disability. In the event that, prior to the payment date (as defined in subsection 4.1 above) of his or her
Award, a Participant suffers a permanent and total disability (as defined in the Company’s long term disability program, regardless of whether the Participant is covered by such program) while employed by the Company or a Subsidiary, resulting
in termination or retirement, subject to Section 6 below, such individual shall be entitled to receive a LTIP Incentive Award, equal to his or her Target Incentive Award, if any, that would otherwise be payable to the Participant under
subsection 3.1 above, pro-rated through the date of termination in accordance with subsection 5.2 below; provided, however, that in no event shall a Participant receive any payment hereunder unless (i) the applicable performance measure (under
subsection 3.3) for the period from the inception of the Performance Period through the last completed full month that occurs on or preceding the Participant’s date of termination is equal to or greater than the Target for that performance
measure, pro-rated through the date of termination in accordance with subsection 5.2 below, (ii) the applicable performance measure is equal to or greater than the applicable Target for the Performance Period, and (iii) as of his date of
termination, the Participant had been employed by one or more of the Company or a Subsidiary, for at least twelve (12) months of the Performance Period applicable to such individual. 

(c) Death. In the event that a Participant dies while employed by the Company or a Subsidiary and prior to the
payment date for his or her Award, his or her Target Incentive Award shall be pro-rated through the date of death, in accordance with subsection 5.2 below, and, subject to Section 6 below, his or her estate shall be entitled to receive a LTIP
Incentive Award, equal to his or her prorated Target Incentive Award and payable in cash; provided, however, that in no event shall a payment be made with respect to a deceased Participant hereunder unless as of his date of death, (i) the

  
 6 

 Lands’ End, Inc. 

Long-Term Incentive Program 
  

 
applicable performance measure (under subsection 3.3) for the period from the inception of the Performance Period through the last completed full month that occurs on or preceding the
Participant’s date of death is equal to or greater than the Target for that performance measure, prorated through the date of death in accordance with subsection 5.2 below, (ii) the applicable performance measure is equal to or greater
than the Target for that performance measure for the Performance Period, and (iii) he had been employed by one or more of the Company or a Subsidiary, for at least twelve (12) months of the Performance Period applicable to such individual.

 5.2. Pro-rations. Any pro-ration of a LTIP Incentive Award, Target Incentive Award, or Target performance measure, as
applicable, under this Section 5 shall be based on a fraction, the numerator of which is the number of full months during the Performance Period in which the Participant was a Participant in the LTIP, and the denominator of which is the full
number of months in the Performance Period, as adjusted in Section 2, if applicable. 
 SECTION 6 

OPERATION AND ADMINISTRATION 

6.1. Compensation Committee and Senior Corporate Compensation Executive. The authority to control and manage the operation and
administration of the LTIP shall be vested in the Compensation Committee and the Senior Corporate Compensation Executive, as provided herein. 

(a) Compensation Committee. Notwithstanding paragraph (b) immediately below, the Compensation Committee: 

(i) Shall approve the Target Incentive Award and the Awards for Participants who are Executives under its purview; 

(ii) With respect to Participants who are Executives, shall have the authority and discretion to establish the terms,
conditions, restrictions, and other provisions of such Awards, and (subject to the restrictions imposed by subsection 6.4 and Section 7) to amend, cancel, or suspend Awards; provided, however (and subject to the requirements of Code
Section 162(m), if applicable) that to the extent the Compensation Committee determines that the restrictions imposed by the LTIP preclude the achievement of the material purposes of the Awards in jurisdictions outside the United States, the
Compensation Committee shall have the authority and discretion to modify those restrictions as the Compensation Committee determines to be necessary or appropriate to conform to applicable requirements or practices of jurisdictions outside of the
United States; 
 (iii) May make additional changes that it deems appropriate for the effective administration of the LTIP,
subject to subsection 6.4 and provided that these changes may not increase the benefits to which Participants may become entitled under the LTIP, nor change the pre-established measures or goals that have been approved except as explicitly provided
in the LTIP; and 
 (iv) Shall be responsible for all other duties and responsibilities allocated to the Compensation
Committee under the terms and conditions of the LTIP. 

  
 7 

 Lands’ End, Inc. 

Long-Term Incentive Program 
  

 (b) Senior Corporate Compensation Executive. Except as provided in
paragraph (a) immediately above, the Senior Corporate Compensation Executive: 
 (i) Shall determine the Target
Incentive Award and the Awards for Participants other than Executives under the purview of the Compensation Committee; 

(ii) Notwithstanding paragraph (a) above, shall have the authority and discretion to establish the terms, conditions,
restrictions, and other provisions of such Awards, and (subject to the restrictions imposed by subsection 6.4 and Section 7) to amend, cancel, or suspend Awards; 

(iii) Shall have the authority to control and manage the operation and administration of the LTIP with respect to all
Participants, subject to the direction of the Compensation Committee with respect to Executives, except as otherwise provided in this LTIP; 

(iv) Shall be responsible for the day-to-day administration of the LTIP except as otherwise provided in this LTIP; and 

(v) Shall be responsible for all other duties and responsibilities allocated to the Senior Corporate Compensation Executive
under the terms and conditions of the LTIP. 
 (c) The Compensation Committee and the Senior Corporate Compensation
Executive, as appropriate, shall have the authority and discretion to interpret the LTIP, to establish, amend, and rescind any rules and regulations relating to the LTIP and to make all other determinations that may be necessary or advisable for the
administration of the LTIP. 
 (d) Any determinations by the Compensation Committee or the Senior Corporate Compensation
Executive, as applicable, regarding this LTIP are binding on the applicable Participants. 
 6.2. Source of Awards. In the
case of Awards under the LTIP that are settled in shares of Stock, such shares shall be distributed under a stock plan adopted by the Company and approved by the shareholders thereof that provides for the issuance of Stock in satisfaction of Awards
hereunder, (which in no event shall be an employee stock purchase plan). In the event of any conflict between this document and such stock plan, the provisions of the stock plan shall govern. 

6.3. Delegation by Compensation Committee. Except to the extent prohibited by applicable law or the applicable rules of a
securities exchange or similar entity, or as would cause Section 162(m) Awards to not satisfy the requirements for performance-based compensation under Code Section 162(m), the Compensation Committee may allocate all or any

  
 8 

 Lands’ End, Inc. 

Long-Term Incentive Program 
  

 
portion of its responsibilities and powers to any one or more of its members and may delegate all or any part of its responsibilities and powers to any person or persons selected by it. The
Compensation Committee may revoke any such allocation or delegation at any time. 
 6.4. Negative Discretion. Notwithstanding
anything in the LTIP to the contrary, prior to the settlement of any LTIP Incentive Award, the Compensation Committee (or the Senior Corporate Compensation Executive with respect to Participants who are not under the purview of the Compensation
Committee) may (a) reduce the amount of such Award, or the number of shares of Stock or amount of cash to be delivered in connection with such Award, and (b) with respect to Awards that are not Section 162(m) Awards, may change the
pre-established measures in goals that have been approved for such Award and increase the amount of such Award or the number of shares of stock or amount of cash to be delivered in connection with such Award. 

6.5. General Restrictions. Delivery of shares of Stock under the LTIP, in satisfaction of a LTIP Incentive Award, shall be
subject to the following: 
 (a) Notwithstanding any other provision of the LTIP, the Company shall have no obligation to
deliver any shares of Stock or make any other distribution of benefits under the LTIP unless such delivery or distribution complies with all applicable laws (including, without limitation, the requirements of the Securities Act of 1933), and the
applicable requirements of any securities exchange or similar entity. 
 (b) To the extent that the LTIP provides for
issuance of Stock certificates to reflect the issuance of shares of Stock, the issuance may be effected on a non-certificated basis, to the extent not prohibited by applicable law or the applicable rules of any exchange or similar entity. 

6.6. Tax Withholding. All distributions under the LTIP are subject to withholding of all applicable taxes. In the case of Awards
under the LTIP that are settled in shares of Stock, if any, the Compensation Committee or Senior Corporate Compensation Executive, as applicable, may condition the delivery of any shares or other benefits under the LTIP on satisfaction of the
applicable withholding obligations. To the extent permitted by the Compensation Committee or Senior Corporate Compensation Executive, as applicable, such withholding obligations may be satisfied: (a) through cash payment by the Participant;
(b) through the surrender of shares of Stock which the Participant already owns (provided, however, that to the extent shares described in this paragraph (b) are used to satisfy more than the minimum statutory withholding obligation, as
described below, then, except as otherwise provided by the Compensation Committee or Senior Corporate Compensation Executive, as applicable, payments made with shares of Stock in accordance with this paragraph (b) shall be limited to shares
held by the Participant for not less than six months prior to the payment date (or such other period of time as the Company’s accountants may require)); or (c) through the surrender of shares of Stock to which the Participant is otherwise
entitled under the LTIP, provided, however, that such shares under this paragraph (c) may be used to satisfy not more than the Company’s minimum statutory withholding obligation (based on minimum statutory withholding rates for Federal and
state tax purposes, including payroll taxes, that are applicable to such supplemental taxable income). 
 6.7. Settlement of
Awards. The obligation to make payments and distributions with respect to Awards may be satisfied through cash payments, the delivery of shares of Stock, or a combination thereof, as provided under subsections 4.1 and 4.2, subject, in the
case of settlement 

  
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Long-Term Incentive Program 
  

 
in shares, to the terms of the stock plan under which the Stock is issued. Satisfaction of any such obligations under an Award, which is sometimes referred to as the “settlement” of the
Award, may be subject to such conditions, restrictions and contingencies as the Compensation Committee or Senior Corporate Compensation Executive, as applicable, shall determine. Each Subsidiary shall be liable for payment of an Award due under the
LTIP with respect to any Participant to the extent that such benefits are attributable to the services rendered for that Subsidiary by the Participant. Any disputes relating to liability of a Subsidiary for payment of an Award shall be resolved by
the Compensation Committee or Senior Corporate Compensation Executive, as applicable. 
 6.8. Transferability. Except as
otherwise provided by the Compensation Committee, Awards under the LTIP are not transferable except as designated by the Participant by will or by the laws of descent and distribution (including Awards originally determined by the Senior Corporate
Compensation Executive). 
 6.9. Form and Time of Elections. Unless otherwise specified herein, each election required
or permitted to be made by any Participant or other person entitled to benefits under the LTIP, and any permitted modification, or revocation thereof, shall be in writing filed with the Compensation Committee or Senior Corporate Compensation
Executive, as applicable, at such times, in such form, and subject to such restrictions and limitations, not inconsistent with the terms of the LTIP, as the Compensation Committee or Senior Corporate Compensation Executive, as applicable, shall
require. 
 6.10. Agreement With Company. Any Award under the LTIP shall be subject to such terms and conditions, not
inconsistent with the LTIP, as the Compensation Committee or Senior Corporate Compensation Executive, as applicable, shall, in its sole discretion, prescribe. The terms and conditions of any Award to any Participant shall be reflected in such form
of written (including electronic) document as is determined by the Compensation Committee. A copy of such document shall be provided to the Participant, and the Compensation Committee or Senior Corporate Compensation Executive, as applicable, may,
but need not, require that the Participant sign a copy of such document. Such document is referred to as an “Award Agreement” regardless of whether any Participant signature is required. 

6.11. Action by Company or Subsidiary. Any action required or permitted to be taken under the LTIP by the Company or any
Subsidiary, if any, of the foregoing shall be by resolution of its board of directors, or by action of one or more members of the board of directors of such company (including a committee of the board) who are duly authorized to act for such board
with respect to the applicable action, or (except to the extent prohibited by applicable law or applicable rules of any securities exchange or similar entity) by a duly authorized officer of such company. 

6.12. Gender and Number. Where the context admits, words in any gender shall include any other gender, words in the singular
shall include the plural and the plural shall include the singular. 
 6.13. Limitation of Implied Rights. 

(a) Neither a Participant nor any other person shall, by reason of participation in the LTIP, acquire any right in or title to
any assets, funds or property of the Company 

  
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Long-Term Incentive Program 
  

 
or any Subsidiary whatsoever, including, without limitation, any specific funds, assets, or other property which the Company or any Subsidiary, in its sole discretion, may set aside in
anticipation of a liability under the LTIP. A Participant shall have only a contractual right to the cash or Stock, if any, payable under the LTIP, unsecured by any assets of the Company or any Subsidiary, and nothing contained in the LTIP shall
constitute a guarantee that the assets of the Company or any Subsidiary shall be sufficient to pay any benefits to any person. 

(b) The LTIP does not constitute a contract of employment, and selection as a Participant shall not give any participating
employee the right to be retained in the employ of the Company or any Subsidiary, nor any right or claim to any benefit under the LTIP, unless such right or claim has specifically accrued under the terms of the LTIP. Except as otherwise provided in
the LTIP, no Award under the LTIP shall confer upon the holder thereof any rights as a shareholder of the Company prior to the date on which the individual fulfills all conditions for receipt of such rights. 

6.14. Evidence. Evidence required of anyone under the LTIP may be by certificate, affidavit, document or other information,
which the person charged with acting on such evidence considers pertinent and reliable, and which has been signed, made or presented by the proper party or parties. 

6.15. Information to be Furnished to the Compensation Committee or Senior Corporate Compensation Executive. The Company and the
Subsidiaries shall furnish the Compensation Committee or Senior Corporate Compensation Executive, as applicable, with such data and information as it determines may be required for it to discharge its duties. The records of the Company and the
Subsidiaries, as to an employee’s or Participant’s employment, termination of employment, leave of absence, reemployment, and compensation shall be conclusive on all persons unless determined to be incorrect. Participants and other persons
entitled to benefits under the LTIP must furnish the Compensation Committee or Senior Corporate Compensation Executive, as applicable, such evidence, data or information as such entity considers desirable to carry out the terms of the LTIP, subject
to any applicable privacy laws. 
 6.16. Corporate Transaction. In the event of a corporate transaction involving the Company
(including without limitation, any Stock dividend, Stock split, extraordinary cash dividend, recapitalization, reorganization, merger, consolidation, split-up, spin-off, sale of assets or subsidiaries, combination or exchange of shares), the
Compensation Committee may adjust Awards to preserve but in no event increase the benefits or potential benefits of the Awards (including Awards originally determined by the Senior Corporate Compensation Executive); provided, however, that no such
adjustment may be made to the extent such adjustment would cause Section 162(m) Awards to cease to qualify as “performance-based compensation” under Code Section 162(m). Actions permitted under the preceding sentence by the
Compensation Committee may include any adjustments that the Compensation Committee determines to be equitable (which may include, without limitation, (a) replacement of Awards with other Awards which the Compensation Committee determines have
comparable value and which are based on stock of a company resulting from the transaction, and (b) cancellation of the Award in return for cash payment of the current value of the Award, determined as though the Award is fully vested at the
time of the payment). 

  
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Long-Term Incentive Program 
  

 6.17. Governing Law. The LTIP will be governed under the internal laws of the
state of Wisconsin without regard to principles of conflicts of laws. The state and federal courts located in the state of Wisconsin shall have exclusive jurisdiction in any action, lawsuit or proceeding based on or arising out of the LTIP. 

6.18. Severability. If any provision(s) of the LTIP shall be found invalid, illegal, or unenforceable, in whole or in part, then
such provision(s) shall be modified or restricted so as to effectuate as nearly as possible in a valid and enforceable way the provisions hereof, or shall be deemed excised from the LTIP, as the case may require, and the LTIP shall be construed and
enforced to the maximum extent permitted by law, as if such provision(s) had been originally incorporated herein as so modified or restricted or as if such provision(s) had not been originally incorporated herein, as the case may be. 

SECTION 7 
 AMENDMENT
AND TERMINATION 
 The Board or Compensation Committee may, at any time, amend or terminate the LTIP, or any Award, provided that no
amendment or termination may, in the absence of written consent to the change by the affected Participant (or, if the Participant is not then living, the affected beneficiary), adversely affect the rights of any Participant or beneficiary under any
Award granted under the LTIP prior to the date such amendment is adopted by the Board or the Compensation Committee, if applicable. No amendment shall be made that would cause the LTIP not to comply with the requirements of any applicable law or
rule of any applicable securities exchange or similar entity, or cause Participants to experience adverse tax consequences under Code Section 409A. The LTIP and any Award thereunder may be amended without Participant consent to the extent that
the Compensation Committee determines such amendment necessary to cause the LTIP or Award to comply with any applicable law or rule of any applicable securities exchange or similar entity, or to prevent adverse tax consequences under Code
Section 409A for Participants. 
 SECTION 8 

DEFINED TERMS 
 8.1.
Each capitalized term in the LTIP is defined where it first appears herein or in this Section 8. In addition to the terms previously defined in the LTIP, the following definitions shall apply: 

(a) Award. The term “Award” or “Awards” means any LTIP Incentive Award(s), whether settled in cash
or Stock. 
 (b) Board. The term “Board” means the Board of Directors of the Company. 

(c) Code. The term “Code” means the Internal Revenue Code of 1986, as amended. A reference to any provision of
the Code shall include reference to any successor provision of the Code (and the regulations issued thereunder). 
 (d)
Compensation Committee. The term “Compensation Committee” refers to the Compensation Committee of the Board of Directors of Lands’ End, Inc. 

  
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Long-Term Incentive Program 
  

 (e) Executive. The term “Executive” refers to any employee
of the Company or a participating Subsidiary who holds a position of senior vice president or higher of Sears Hometown and Outlet Stores, Inc. (not of any subsidiary or affiliate) or any employee who is an officer under Section 16(b) of the
Securities and Exchange Act of 1934 with respect to Lands’ End, Inc. 
 (f) Fiscal Year. The capitalized term
“Fiscal Year” refers to the fiscal year of the Company. 
 (g) Section 162(m) Award. The term
“Section 162(m) Award” refers to any Award that is designated by the Compensation Committee as intended to meet the requirements for “performance-based compensation” under Code Section 162(m). 

(h) Senior Corporate Compensation Executive. The term “Senior Corporate Compensation Executive” refers to the
most senior human resources and compensation executive (or equivalent) or if he or she has explicitly delegated his or her duties with respect to the LTIP, as provided herein, then the Senior Corporate Compensation Executive shall refer to such
authorized representative to whom the duties of administering the LTIP have been delegated. 
 (i) Subsidiary. The
term “Subsidiary” or “Subsidiaries” refers to any company during any period in which it is a “subsidiary corporation” (as that term is defined in Section 424(f) of the Code) with respect to the Company. 

SECTION 9 
 EXPIRATION
OF LTIP 
 A payment obligation under the LTIP with respect to a specific Performance Period shall expire, subject to earlier
termination pursuant to Section 7, on the date on which all LTIP Incentive Awards (if any) for the Performance Period are paid in full or would have been payable in accordance with the provisions of the LTIP (or, if earlier, on the date that
the Compensation Committee determines that the results are less than the Thresholds for the performance measures) with respect to such Performance Period. Notwithstanding this Section 9, the Company’s right to reimbursement under
Section 3.7 will continue to survive after the expiration of the LTIP. 

  
 13

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