Exhibit 10.4

ROLLOVER AGREEMENT

This Rollover Agreement (this “Agreement”) is made and entered into as of
June 6, 2012, by and among Cole Family Holdco, LLC, a Delaware limited liability
company (“Family LLC”), and the stockholders (“Family Stockholders”) of Kenneth
Cole Productions, Inc. (the “Company”) listed on Annex A attached hereto.

WHEREAS, concurrent with the execution and delivery of this Agreement, KCP
Holdco, Inc., a Delaware corporation and wholly-owned subsidiary of Family LLC
(“Parent”), KCP MergerCo, Inc., a New York corporation and wholly-owned
subsidiary of Parent (“Merger Sub”), and the Company are entering into an
Agreement and Plan of Merger (the “Merger Agreement”), which provides, among
other things, for the merger of Merger Sub with and into the Company, with the
Company surviving as a wholly-owned subsidiary of Parent (the “Merger”);

WHEREAS, as of the date hereof, each Family Stockholder is the beneficial owner
of, and has the sole or shared right to vote and dispose of, (i) that number of
shares of Class A Common Stock, par value $0.01 per share, of the Company
(“Class A Stock”) and (ii) that number of shares of Class B Common Stock, par
value $0.01 per share, of the Company (“Class B Stock” and together with Class A
Stock, “Rollover Shares”), set forth opposite such Family Stockholder’s name on
Annex A hereto; and

WHEREAS, subject to the conditions set forth herein, immediately prior to the
Effective Time (as defined in the Merger Agreement), (i) each Family Stockholder
desires to exchange that number of Rollover Shares set forth opposite such
Family Stockholder’s name on Annex A hereto and (ii) Family LLC desires to issue
to such Family Stockholder, in exchange for such Rollover Shares, membership
units in Family LLC (“Family LLC Units”) as set forth opposite each Family
Stockholder’s name on Annex A hereto.

NOW, THEREFORE, in consideration of the mutual promises, covenants,
representations and warranties contained herein, the parties hereto agree as
follows:

1. Rollover.

(a) Immediately prior to the Effective Time, (i) each Family Stockholder will
assign, transfer, convey and deliver such Family Stockholder’s Rollover Shares
to Family LLC, and in exchange for such Rollover Shares, Family LLC shall issue
and deliver to such Family Stockholder the number of Family LLC Units set forth
opposite such Family Stockholder’s name on Annex A (collectively, the
“Rollover”) and (ii) any and all Family LLC Units previously issued shall cease
to be outstanding and shall automatically be cancelled and shall cease to exist.
No Family Stockholder shall be required under any circumstance to contribute, or
cause to be contributed, to Family LLC a number of Rollover Shares in excess of
the number of Rollover Shares set forth opposite such Family Stockholder’s name
on Annex A hereto.

(b) In the event that the Rollover is consummated but the Merger Agreement is
terminated in accordance with its terms, then the Rollover will be void ab
initio and deemed not to have occurred and each Family Stockholder will deliver
to Family LLC

--------------------------------------------------------------------------------

the number of Family LLC Units received by such Family Stockholder pursuant to
paragraph (a) of this Section 1 and Family LLC will deliver to each Family
Stockholder the Rollover Shares previously delivered by such Family Stockholder
to Family LLC.

2. Closing.

(a) The closing of the transactions contemplated by this Agreement (the
“Rollover Closing”) will take place at the offices of Willkie Farr & Gallagher
LLP, 787 Seventh Avenue, New York, New York 10019, immediately prior to the
Effective Time.

(b) At the Rollover Closing, each Family Stockholder will deliver to Family LLC
stock certificates duly endorsed for transfer to Family LLC, or accompanied by
stock powers duly endorsed in blank, representing each such Family Stockholder’s
Rollover Shares, and Family LLC will reflect on its books and records such
Family Stockholder’s ownership of the number of Family LLC Units set forth
opposite such Family Stockholder’s name on Annex A.

3. Representations and Warranties of the Investors. Each Family Stockholder
represents and warrants, severally but not jointly, as follows:

(a) Binding Agreement. Such Family Stockholder has the capacity to execute and
deliver this Agreement and to consummate the transactions contemplated hereby,
and (i) in the case of each Family Stockholder that is an individual, the
execution and delivery of this Agreement does not require any consent from such
Family Stockholder’s spouse or any other person, and (ii) in the case of each
Family Stockholder that is a trust, Robyn Transport is such Family Stockholder’s
trustee and has the authority to execute and deliver this Agreement on behalf of
such Family Stockholder. Such Family Stockholder has duly and validly executed
and delivered this Agreement and this Agreement constitutes a legal, valid and
binding obligation of such Family Stockholder, enforceable against such Family
Stockholder in accordance with its terms, except as such enforceability may be
limited by applicable bankruptcy, insolvency, reorganization or other similar
laws affecting creditors’ rights generally and by general equitable principles
(regardless of whether enforceability is considered in a proceeding in equity or
at law).

(b) Ownership of Shares. Such Family Stockholder is the “beneficial owner” (as
defined in Rule 13d-3 under the Securities Exchange Act of 1934, as amended,
which meaning will apply for all purposes of this Agreement) of, and has the
sole (or shared with one or more other Family Stockholders) power to vote and
dispose of the number of Rollover Shares set forth opposite such Family
Stockholder’s name in Annex A hereto free and clear of any security interests,
liens, charges, encumbrances, equities, claims, options or limitations of
whatever nature and free of any other limitation or restriction (including any
restriction on the right to vote, sell or otherwise dispose of such Rollover
Shares), except as may exist by reason of this Agreement or pursuant to
applicable law. Except as provided for in this Agreement, there are no
outstanding options or other rights to acquire from such Family Stockholder, or
obligations of such Family Stockholder to sell or to dispose of, any of such
Rollover Shares.

 

2

--------------------------------------------------------------------------------

(c) No Conflict. Neither the execution and delivery of this Agreement, nor the
consummation of the transactions contemplated hereby, nor the performance of
such Family Stockholder’s obligations hereunder will (a) result in a violation
or breach of, or constitute (with or without due notice or lapse of time or
both) a default (or give rise to any right of termination, cancellation, or
acceleration) under any contract, agreement, instrument, commitment, arrangement
or understanding to which such Family Stockholder is a party, or result in the
creation of a security interest, lien, charge, encumbrance, equity or claim with
respect to such Family Stockholder’s Rollover Shares, or (b) require any
material consent, authorization or approval of any person, entity or
governmental entity, or (c) violate or conflict with any writ, injunction or
decree applicable to such Family Stockholder or such Family Stockholder’s
Rollover Shares.

(d) Accredited Investor. Such Family Stockholder is an “accredited investor” as
such term is defined in Rule 501(a) promulgated under the Securities Act of
1933, as amended (the “Securities Act”).

(e) Investor’s Experience. Such Family Stockholder’s financial situation is such
that the Family Stockholder can afford to bear the economic risk of holding the
Family LLC Units to be received by such Family Stockholder, and such Family
Stockholder can afford to suffer complete loss of its investment in such Family
LLC Units. Such Family Stockholder’s knowledge and experience in financial and
business matters are such that the Family Stockholder is capable of evaluating
the merits and risks of the Family Stockholder’s investment in such Family LLC
Units.

(f) Investment Intent. Such Family Stockholder is acquiring Family LLC Units
solely for the Family Stockholder’s own account for investment and not with a
view to or for sale in connection with any distribution thereof. The Family
Stockholder agrees that the Family Stockholder will not, directly or indirectly,
offer, transfer, sell, pledge, hypothecate or otherwise dispose of any Family
LLC Units (or solicit any offers to buy, purchase or otherwise acquire or take a
pledge of any of the Family LLC Units), except in compliance with (i) the
Securities Act and the rules and regulations of the Securities and Exchange
Commission thereunder, (ii) applicable state and non-U.S. securities or “blue
sky” laws and (iii) the provisions of this Agreement and any other agreement
among the Family Stockholders.

4. Conditions Precedent. The obligations of each Family Stockholder to
consummate the transactions contemplated hereby are subject to the conditions
set forth in Sections 6.01 and 6.02 of the Merger Agreement being satisfied or
waived by Parent (other than any conditions that by their nature are to be
satisfied at the Closing, but subject to the prior or substantially concurrent
satisfaction of such conditions), and such other conditions set forth in the
Equity Commitment Letter, dated of even date herewith, among the Family
Stockholders, Family LLC, Parent and the Company (the “Equity Commitment
Letter”).

5. Certain Approvals. Each Family Stockholder hereby acknowledges that the
Principal Stockholder, as the managing member of Family LLC, may take any and
all actions on behalf of Family LLC in its sole discretion, including voting the
shares of Parent held by Family LLC, before the Effective Time.

 

3

--------------------------------------------------------------------------------

6. Operating Agreement. Simultaneous with the Effective Time, each Family
Stockholder shall enter into the Amended and Restated Limited Liability Company
Agreement of Parent, in such form to be agreed among the Family Stockholders
prior to Closing.

7. Tax Matters.

The parties hereto (i) shall treat the Rollover as a tax-free partnership
contribution under Section 721 of the Internal Revenue Code of 1986, as amended,
for all federal, state and local income tax purposes, and (ii) will not take any
position on any return that is inconsistent with such treatment.

8. Miscellaneous.

(a) Notices. All notices and other communications hereunder shall be in writing
and shall be deemed to have been duly given if delivered personally or sent by
telecopy, overnight courier service or by registered or certified mail (postage
prepaid, return receipt requested), to any Family Stockholder at the address of
such Family Stockholder set forth on Annex A (or at such other address as shall
be specified by such Family Stockholder by like notice) and to Family LLC, at
the following address or at such other address as shall be specified by Family
LLC by like notice:

to:

Cole Family Holdco, LLC

c/o Kenneth Cole Productions, Inc.

603 West 50th Street

New York, NY 10019

Telecopier: 1-866-698-7042

Attention: Kenneth D. Cole

with a copy to (which shall not constitute notice):

Willkie Farr & Gallagher LLP

787 Seventh Avenue

New York, New York 10019

Telecopier: (212) 728-9129

Attention: Adam M. Turteltaub

(b) Binding Effect; Benefits.

(i) This Agreement will be binding upon the successors, heirs, executors and
administrators of the parties hereto. Except as set forth in Section 8(b)(ii)
and other than as set forth in the Equity Commitment Letter, nothing in this
Agreement, express or implied, is intended or will be construed to give any
person other than the parties to this Agreement and their respective successors
or permitted assigns any legal or equitable right, remedy or claim under or in
respect of any agreement or any provision contained herein.

 

4

--------------------------------------------------------------------------------

(ii) Notwithstanding anything to the contrary in this Agreement, each of the
parties acknowledges and agrees that the Company is hereby made a third party
beneficiary of this Agreement for the purposes of enforcing (including specific
performance of) Parent’s rights to cause the Rollover to be consummated in
accordance with the terms hereof, solely to the extent expressly provided and
permitted by the terms and conditions of Section 8.08(b) of the Merger Agreement
and the terms and conditions hereof.

(c) Amendments. This Agreement may not be modified, amended, altered or
supplemented except upon the execution and delivery of a written agreement
executed by all of the parties hereto and the Company and in accordance with the
terms of the Equity Commitment Letter.

(d) Assignability. Neither this Agreement nor any right, remedy, obligation or
liability arising hereunder or by reason hereof will be assignable by any Family
Stockholder without the prior written consent of Family LLC and the Company and
in accordance with the terms of the Equity Commitment Letter; provided that,
without the prior written consent of the Company, a Family Stockholder may
assign its rights hereunder in connection with any Permitted Transfer (as
defined in the Voting Agreement) under the terms of the Voting Agreement (a
“Permitted Assignee”), provided that any Permitted Assignee shall, as a
condition to any such assignment, execute a joinder agreement, in form and
substance reasonably satisfactory to the Company, whereby the Permitted Assignee
agrees to be bound by the provisions of this Agreement applicable to the Family
Stockholders.

(e) Governing Law. This Agreement shall be governed by and construed in
accordance with the laws of the State of New York, regardless of the laws that
might otherwise govern under applicable principles of conflicts of laws thereof,
except to the extent that mandatory provisions of federal law apply. Each of the
parties hereto hereby irrevocably and unconditionally submits, for itself and
its property, to the exclusive jurisdiction of the courts of the State of New
York and any appellate court thereof and the United States District Court for
the Southern District of New York and any appellate court thereof, in any action
or proceeding arising out of or relating to this Agreement or the agreements
delivered in connection herewith or the transactions contemplated hereby or
thereby or for recognition or enforcement of any judgment relating thereto, and
each of the parties hereby irrevocably and unconditionally (i) agrees not to
commence any such action except in such courts, (ii) agrees that any claim in
respect of any such action or proceeding may be heard and determined in such
courts, (iii) waives, to the fullest extent it may legally and effectively do so
any objection which it may now or hereafter have to venue of any such action or
proceeding in any such courts, and (iv) waives, to the fullest extent permitted
by law, the defense of any inconvenient forum to the maintenance of such action
or proceeding in any such courts. Each of the parties hereto agrees that a final
judgment in any such action or proceeding shall be conclusive and may be
enforced in other jurisdictions by suit on the judgment or in any other manner
provided by law. Each of the parties to this Agreement irrevocably consents to
service of process in any such action or proceeding in the manner provided for
notices in Section 8(a) of this Agreement; provided, however, that nothing in
this Agreement shall affect the right of any party to this Agreement to serve
process in any other manner permitted by law.

 

5

--------------------------------------------------------------------------------

(f) Counterparts. This Agreement may be executed by facsimile and in two or more
counterparts, each of which will be deemed to be an original, but all of which
together will constitute one and the same instrument.

(g) Severability. If any term or other provision of this Agreement is invalid,
illegal or incapable of being enforced by any rule of law, or public policy, all
other conditions and provisions of this Agreement will nevertheless remain in
full force and effect so long as the economic or legal substance of the
transactions contemplated herein are not affected in any manner materially
adverse to any party hereto. Upon such determination that any term or other
provision is invalid, illegal or incapable of being enforced, the parties hereto
will negotiate in good faith to modify this Agreement so as to effect the
original intent of the parties as closely as possible in a mutually acceptable
manner.

(h) Waiver. Any party to this Agreement may waive any condition to their
obligations contained herein.

(i) Termination. This Agreement will terminate on the earlier of the termination
of the Merger Agreement in accordance with its terms or the expiration or
termination of the obligations of Family LLC and the Family Stockholders under
the Equity Commitment Letter. Termination will not relieve any party from
liability for any breach of its obligations hereunder committed prior to such
termination.

(j) Further Assurances. Each party to this Agreement shall execute such
documents and other papers and take such further actions as may be reasonably
required or desirable to carry out the provisions hereof and the transactions
contemplated hereby.

(k) Effectiveness. The obligations of the Family Stockholders under this
Agreement shall not be effective or binding upon the Family Stockholders until
such time as the Merger Agreement is executed and delivered by the parties
thereto.

(l) Definitions. Capitalized terms not otherwise defined herein have the
meanings ascribed to such terms in the Merger Agreement.

[Signatures on the following page]

 

6

--------------------------------------------------------------------------------

IN WITNESS WHEREOF, the parties hereto have executed this Agreement as of the
date first above written.

 

COLE FAMILY HOLDCO, LLC By:   /s/ Kenneth D. Cole  

Name: Kenneth D. Cole

Title: Manager

KMC PARTNERS L.P. By:   KMC Partners LLC, its general partner By:   /s/ Kenneth
D. Cole  

Name: Kenneth D. Cole

Title: Managing Member

  /s/ Kenneth D. Cole   Kenneth D. Cole   /s/ Robyn S. Transport  

Robyn S. Transport, as Trustee of the Family Trust u/a/d 4/26/10, KDC July 2010
GRAT

u/a/d 7/12/10, KDC 2009 GRAT u/a/d 2/2/09, KDC 2009 Family GRAT u/a/d 2/2/09 and

Kenneth Cole 1994 Charitable Remainder Trust u/a/d 12/19/94

 

[Signature Page to Rollover Agreement]

--------------------------------------------------------------------------------

Annex A

 

Name and Address of Family

              Stockholder

   Class A
Rollover
Shares      Class B
Rollover
Shares      Class A
Family
LLC
Units      Class B
Family LLC
Units  

KMC Partners L.P.

c/o Kenneth D. Cole

Kenneth Cole Productions, Inc.

603 West 50th Street

New York, NY 10019

     0         187,500         0         187.500   

Kenneth D. Cole

c/o Kenneth Cole Productions, Inc.

603 West 50th Street

New York, NY 10019

     353,653         6,424,792         353.653         6,424.792   

Robyn Transport as Trustee of the

Family Trust u/a/d 4/26/10

c/o Robyn Transport

TAG Associates, LLC

75 Rockefeller Plaza, 9th Floor

New York, NY 10019

     0         132,021         0         132.021   

KDC July 2010 GRAT u/a/d

7/12/10

c/o Robyn Transport

TAG Associates, LLC

75 Rockefeller Plaza, 9th Floor

New York, NY 10019

     0         204,852         0         204.852   

KDC 2009 GRAT u/a/d 2/2/09

c/o Robyn Transport

TAG Associates, LLC

75 Rockefeller Plaza, 9th Floor

New York, NY 10019

     0         470,666         0         470.666   

KDC 2009 Family GRAT u/a/d

2/2/09

c/o Robyn Transport

TAG Associates, LLC

75 Rockefeller Plaza, 9th Floor

New York, NY 10019

     0         470,666         0         470.666   

--------------------------------------------------------------------------------

Name and Address of Family

              Stockholder

   Class A
Rollover
Shares      Class B
Rollover
Shares      Class A
Family
LLC
Units      Class B
Family
LLC
Units  

Kenneth Cole 1994 Charitable

Remainder Trust u/a/d 12/19/94

c/o Robyn Transport

TAG Associates, LLC

75 Rockefeller Plaza, 9th Floor

New York, NY 10019

     150,000         0         150.000         0