<PAGE>

                                  EXHIBIT 10.27

                          PHOENIX FOOTWEAR GROUP, INC.

                                Lock-Up Agreement

                                  May 25, 2004

Wedbush Morgan Securities, Inc.
1000 Wilshire Boulevard, 10th Floor
Los Angeles, CA 90017

First Albany Capital Inc.
One Penn Plaza, 42nd Floor
New York, NY 10119

Re:   Phoenix Footwear Group, Inc. - Lock-Up Agreement

Ladies and Gentlemen:

      The undersigned understands that you, as managing underwriters, propose to
enter into an Underwriting Agreement (the "Underwriting Agreement") on behalf of
the several Underwriters named in such agreement (collectively, the
"Underwriters"), with Phoenix Footwear Group, Inc., a Delaware corporation (the
"Company"), providing for a public offering of shares (the "Shares") of the
common stock of the Company (the "Common Stock") pursuant to a Registration
Statement on Form S-2 (the "Registration Statement") filed with the Securities
and Exchange Commission (the "SEC").

      In consideration of the agreement by the Underwriters to continue their
efforts in connection with the offering of the Shares, and of other good and
valuable consideration, the receipt and sufficiency of which are hereby
acknowledged, the undersigned agrees that, during the period beginning on the
date hereof and continuing to and including the date 180 days after the date of
such final prospectus, the undersigned will not offer, sell, contract to sell,
pledge, grant any option to purchase, make any short sale or otherwise dispose
of any shares of Common Stock, or any options or warrants to purchase any shares
of Common Stock, or any securities convertible into, exchangeable for or that
represent the right to receive shares of Common Stock, whether now owned or
hereinafter acquired, owned directly by the undersigned (including holding as a
custodian) or with respect to which the undersigned has beneficial ownership
within the rules and regulations of the SEC (collectively the "Undersigned's
Shares").

      The foregoing restriction is expressly agreed to preclude the undersigned
from engaging in any hedging or other transaction which is designed to or
reasonably expected to lead to, or result in, a sale or disposition of the
Undersigned's Shares even if such Shares would be disposed of by someone other
than the undersigned. Such prohibited hedging or other transactions would
include without limitation any short sale (whether or not against the box) or
any purchase, sale or grant of any right (including without limitation any put
or call option) with respect to any of the Undersigned's Shares or with respect
to any security that includes, relates to, or derives any significant part of
its value from such Shares.

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      The undersigned further represents and agrees that the undersigned has not
taken and will not take, directly or indirectly, any action which is designed to
or which has constituted or which might reasonably be expected to cause or
result in stabilization or manipulation of the price of any security of the
Company to facilitate the sale or resale of the Shares, or which has otherwise
constituted or will constitute any prohibited bid for or purchase of the Shares
or any related securities.

      Notwithstanding the foregoing, the undersigned may transfer the
Undersigned's Shares (i) as a bona fide gift or gifts, provided that the donee
or donees thereof agree to be bound by the restrictions set forth herein, (ii)
to any trust for the direct or indirect benefit of the undersigned or the
immediate family of the undersigned, provided that the trustee of the trust
agrees to be bound by the restrictions set forth herein, and provided further
that any such transfer shall not involve a disposition for value, (iii) pursuant
to the Registration Statement or (iv) with the prior written consent of the
managing underwriters on behalf of the Underwriters. For purposes of this
Lock-Up Agreement, "immediate family" shall mean any relationship by blood,
marriage or adoption, not more remote than first cousin. The undersigned now
has, and, except as contemplated by clause (i), (ii), (iii) or (iv) above, for
the duration of this Lock-Up Agreement will have, good and marketable title to
the Undersigned's Shares, free and clear of all liens, encumbrances, and claims
whatsoever. The undersigned also agrees and consents to the entry of stop
transfer instructions with the Company's transfer agent and registrar against
the transfer of the Undersigned's Shares except in compliance with the foregoing
restrictions.

      Notwithstanding anything contained herein to the contrary, this Lock-Up
Agreement shall terminate and be of no further force or effect upon written
notice either by the Company to the Underwriters or by the Underwriters to the
Company that the offering of the Shares has been terminated or suspended.

      The undersigned understands that the, Company and the Underwriters are
relying upon this Lock-Up Agreement in proceeding toward consummation of the
offering. The undersigned further understands that this Lock-Up Agreement is
irrevocable and shall be binding upon the undersigned's heirs, legal
representatives, successors, and assigns.

                                      Very truly yours,

                                      James R. Riedman
                                      ------------------------------------------
                                      Exact Name of Shareholder

                                      /s/ James R. Riedman
                                      ------------------------------------------
                                      Authorized Signature

                                      ------------------------------------------
                                      Title: -----------------------------------

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              SCHEDULE TO EXHIBIT 10.27 - FORM OF LOCK-UP AGREEMENT
                BY AND AMONG PHOENIX FOOTWEAR GROUP, INC. AND THE
          DIRECTORS, OFFICERS AND PRINCIPAL SHAREHOLDERS OF THE COMPANY

The Lock-Up Agreement filed as Exhibit 10.26 is substantially identical in all
material respects to the lock-up agreements which have been entered into by the
following directors, officers and principal shareholders of the Company dated as
of the date set forth to their names:

<TABLE>
<CAPTION>
      Name                         Date of Lock-Up Agreement
      ----                         -------------------------
<S>                                <C>
Steve DePerrior                           May 26, 2004

Gregory M. Harden                         May 26, 2004

John C. Kratzer                           May 22, 2004

Wilhelm Pfander                           April 5, 2004

Frederick R. Port                         May 26, 2004

John M. Robbins                           May 25, 2004

Gregory A. Tunney                         May 25, 2004

Richard E. White                          May 26, 2004

Kenneth E. Wolf                           May 26, 2004
</TABLE>