EXHIBIT 10.53

                   SERIES E PREFERRED STOCK PURCHASE AGREEMENT

        THIS SERIES E PREFERRED STOCK PURCHASE AGREEMENT, dated as of May 21,
2003 (this "Agreement"), is entered into by and between BLUEFLY, INC., a
Delaware corporation (the "Company"), and the investors listed on Schedule 1
hereto (each, an "Investor" and, collectively, the "Investors").

                                    RECITALS

        WHEREAS, the Company and the Investors are parties to that certain
Series D Preferred Stock Purchase Agreement, dated as of March 12, 2003 (the
"Series D Purchase Agreement");

        WHEREAS, pursuant to section 5.2 of the Series D Preferred Stock
Purchase Agreement, the Investors agreed, subject to the terms and conditions
contained therein, to provide the Company with up to $1,000,000 of additional
financing during 2003 (the "Standby Commitment");

        WHEREAS, the Investors desire to purchase from the Company, and the
Company desires to issue and sell to the Investors, 1,000 shares (the "Shares")
of Series E Convertible Preferred Stock, par value $.01 per share (the "Series E
Preferred Stock"), of the Company on the terms, and subject to the conditions,
contained herein, and in full satisfaction of the Standby Commitment.

        NOW, THEREFORE, in consideration for the mutual covenants contained
herein, and for other good and valuable consideration, the receipt and
sufficiency of which are hereby acknowledged, the parties hereto, intending to
be legally bound, agree as follows:

                                    AGREEMENT

                                    ARTICLE I
                           PURCHASE AND SALE OF SHARES

        Subject to the terms and conditions hereof, the Company hereby issues
and sells to the Investors, and each Investor hereby purchases from the Company,
the number of Shares set forth opposite such Investor's name in Schedule 1, for
a purchase price of one thousand dollars ($1,000) per Share, resulting in an
aggregate purchase price for all Shares sold pursuant to the terms hereof of
$1,000,000 (the "Purchase Price").

                                   ARTICLE II
                  REPRESENTATIONS AND WARRANTIES OF THE COMPANY

        The Company represents and warrants to the Investors as follows:

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        SECTION 2.1 Organization, etc. The Company and its Subsidiary (as
defined in Section 2.4(b)) have each been duly formed, and are each validly
existing as a corporation in good standing under the laws of their respective
States of incorporation, and are each qualified to do business as a foreign
corporation in each jurisdiction in which the failure to be so qualified could
reasonably be expected to have a material adverse effect on the assets,
liabilities, condition (financial or other), business or results of operations
of the Company and its Subsidiary taken as a whole (a "Material Adverse
Effect"). The Company and its Subsidiary each have the requisite corporate power
and authority to own, lease and operate their respective properties and to
conduct their respective businesses as presently conducted. The Company has the
requisite corporate power and authority to enter into, execute, deliver and
perform all of its duties and obligations under this Agreement and to consummate
the transactions contemplated hereby.

        SECTION 2.2 Authorization. The execution, delivery and performance of
this Agreement and the issuance of the Shares have been duly authorized by all
necessary corporate action on the part of the Company, including, without
limitation, the due authorization by the affirmative votes of a majority of the
disinterested directors of the Company's Board of Directors.

        SECTION 2.3 Validity; Enforceability. This Agreement has been duly
executed and delivered by the Company, and constitutes the legal, valid and
binding obligation of the Company, enforceable against the Company in accordance
with its terms, except as such enforceability may be limited by, or subject to,
any bankruptcy, insolvency, reorganization, moratorium or similar laws affecting
the enforcement of creditors' rights generally and subject to general principles
of equity.

        SECTION 2.4 Capitalization.

                (a)     As of the date hereof, the authorized capital stock of
the Company consists of 92,000,000 shares of common stock, $0.01 par value per
share (the "Common Stock"), and 25,000,000 shares of preferred stock, $0.01 par
value per share, of which 500,000 shares have been designated Series A
Convertible Preferred Stock, 9,000,000 shares have been designated Series B
Convertible Preferred Stock, 3,500 shares have been designated Series C
Convertible Preferred Stock, 7,150 shares have been designated Series D
Convertible Preferred Stock and 1,000 shares have been designated Series E
Convertible Preferred Stock. Without giving effect to the transactions
contemplated by this Agreement, the issued and outstanding capital stock of the
Company consists of (i) 11,024,568 Shares of Common Stock, (ii) 460,000 shares
of Series A Convertible Preferred Stock, (iii) 8,889,414 shares of Series B
Convertible Preferred Stock, (iv) 1,000 shares of Series C Convertible Preferred
Stock and (v) 7,136.548 Shares of Series D Convertible Preferred Stock. All such
shares of the Company have been duly authorized and are fully paid and
non-assessable. Except as set forth on Schedule 2.4 hereto or as otherwise
contemplated by this Agreement, there are no outstanding options, warrants or
other equity securities that are convertible into, or exercisable for, shares of
the Company's capital stock.

                (b)     The only Subsidiary of the Company is Clothesline
Corporation. The Company owns all of the issued and outstanding capital stock of
its Subsidiary, free and clear of all

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liens and encumbrances. All of such shares of capital stock are duly authorized,
validly issued, fully paid and non-assessable, and were issued in compliance
with the registration and qualification requirements of all applicable federal,
state and foreign securities laws. There are no options, warrants, conversion
privileges, subscription or purchase rights or other rights presently
outstanding to purchase or otherwise acquire any authorized but unissued,
unauthorized or treasury shares of capital stock or other securities of, or any
proprietary interest in, the Company's Subsidiary, and there is no outstanding
security of any kind convertible into or exchangeable for such shares or
proprietary interest. "Subsidiary" means, with respect to the Company, a
corporation or other entity of which 50% or more of the voting power of the
outstanding voting equity securities or 50% or more of the outstanding economic
equity interest is held, directly or indirectly, by the Company.

        SECTION 2.5 Governmental Consents. The execution and delivery by the
Company of this Agreement, and the performance by the Company of the
transactions contemplated hereby, do not and will not require the Company to
effectuate or obtain any registration with, consent or approval of, or notice to
any federal, state or other governmental authority or regulatory body, other
than periodic and other filings under the Securities Exchange Act of 1934, as
amended (the "Exchange Act") and listing applications and/or notifications to
The Nasdaq SmallCap Market and The Boston Stock Exchange with respect to the
issuance of the Shares and/or the shares of Common Stock issuable upon
conversion of the Shares. The parties hereto agree and acknowledge that, in
making the representations and warranties in the foregoing sentence of this
Section 2.5, the Company is relying on the representations and warranties made
by the Investors in Section 3.4.

        SECTION 2.6 No Violation. The execution and delivery of this Agreement
and the performance by the Company of the transactions contemplated hereby will
not (i) conflict with or result in a breach of any provision of the articles of
incorporation or by-laws of the Company, (ii) result in a default or breach of,
or, except for the approval of the holders of the Company's Series A Convertible
Preferred Stock, the Series B Convertible Preferred Stock, the Series C
Convertible Preferred Stock and the Series D Convertible Preferred Stock,
require any consent, approval, authorization or permit of, or filing or
notification to, any person, company or entity under any of the terms,
conditions or provisions of any note, bond, mortgage, indenture, loan, factoring
arrangement, license, agreement, lease or other instrument or obligation to
which the Company or its Subsidiary is a party or by which the Company or its
Subsidiary or any of their respective assets may be bound or (iii) violate any
law, judgment, order, writ, injunction, decree, statute, rule or regulation of
any court, administrative agency, bureau, board, commission, office, authority,
department or other governmental entity applicable to the Company or its
Subsidiary, except, in the case of clause (ii) or (iii) above, any such event
that could not reasonably be expected to have a Material Adverse Effect or
materially impair the transactions contemplated hereby.

        SECTION 2.7 Issuance of Shares. The Shares have been validly issued,
and, upon payment therefor, will be fully paid and non-assessable. The offering,
issuance, sale and delivery of the Shares as contemplated by this Agreement are
exempt from the registration and prospectus delivery requirements of the
Securities Act of 1933, as amended (the "Securities Act"), are being made in
compliance with all applicable federal and (except for any violation or
non-compliance that could

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not reasonably be expected to have a Material Adverse Effect) state laws and
regulations concerning the offer, issuance and sale of securities, and are not
being issued in violation of any preemptive or other rights of any stockholder
of the Company. The parties hereto agree and acknowledge that, in making the
representations and warranties in the foregoing sentence of this Section 2.7,
the Company is relying on the representations and warranties made by the
Investors in Section 3.4.

        SECTION 2.8 Absence of Certain Developments. Since March 31, 2003, there
has not been any: (i) material adverse change in the condition, financial or
otherwise, of the Company and its Subsidiary (taken as a whole) or in the
assets, liabilities, properties or business of the Company and its Subsidiary
(taken as a whole); (ii) declaration, setting aside or payment of any dividend
or other distribution with respect to, or any direct or indirect redemption or
acquisition of, any capital stock of the Company; (iii) waiver of any valuable
right of the Company or its Subsidiary or cancellation of any material debt or
claim held by the Company or its Subsidiary; (iv) material loss, destruction or
damage to any property of the Company or its Subsidiary, whether or not insured;
(v) acquisition or disposition of any material assets (or any contract or
arrangement therefor) or any other material transaction by the Company or its
Subsidiary otherwise than for fair value in the ordinary course of business
consistent with past practice; or (vi) other agreement or understanding, whether
in writing or otherwise, for the Company or its Subsidiary to take any action of
the type, or any action that would result in an event of the type, specified in
clauses (i) through (v).

        SECTION 2.9 Commission Filings. The Company has filed all required
forms, reports and other documents with the Securities and Exchange Commission
(the "Commission") for periods from and after January 1, 2002 (collectively, the
"Commission Filings"), each of which has complied in all material respects with
all applicable requirements of the Securities Act and/or the Exchange Act (as
applicable). The Company has heretofore made available to the Investors all of
the Commission Filings, including the Company's Annual Report on Form 10-K for
the year ended December 31, 2002 and the Company's Quarterly Report on Form 10-Q
for the quarterly period ended March 31, 2003. As of their respective dates, the
Commission Filings did not contain any untrue statement of a material fact or
omit to state a material fact necessary in order to make the statements made, in
light of the circumstances under which they were made, not misleading. The
audited consolidated financial statements and unaudited interim consolidated
financial statements of the Company included or incorporated by reference in
such Commission Filings have been prepared in accordance with generally accepted
accounting principles, consistently applied ("GAAP") (except as may be indicated
in the notes thereto or, in the case of the unaudited consolidated statements,
as permitted by Form 10-Q), complied as of their respective dates in all
material respects with applicable accounting requirements and the published
rules and regulations of the Commission with respect thereto, and fairly
present, in all material respects, the consolidated financial position of the
Company and its Subsidiary as of the dates thereof and the results of operations
for the periods then ended (subject, in the case of any unaudited consolidated
interim financial statements, to the absence of footnotes required by GAAP and
normal year-end adjustments).

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        SECTION 2.10 Brokers. Neither the Company, nor any of its officers,
directors or employees, has employed any broker or finder, or incurred any
liability for any brokerage fees, commissions, finder's or other similar fees or
expenses in connection with the transactions contemplated hereby.

                                   ARTICLE III
                 REPRESENTATIONS AND WARRANTIES OF THE INVESTORS

        Each Investor represents and warrants to the Company, severally but not
jointly, as follows:

        SECTION 3.1 Organization, etc. Such Investor has been duly formed and is
validly existing and in good standing under the laws of its jurisdiction of
organization. Such Investor has the requisite organizational power and authority
to enter into, execute, deliver and perform all of its duties and obligations
under this Agreement and to consummate the transactions contemplated hereby.

        SECTION 3.2 Authority. The execution, delivery and performance of this
Agreement have been duly authorized by all necessary organizational or other
action on the part of such Investor.

        SECTION 3.3 Validity; Enforceability. This Agreement has been duly
executed and delivered by such Investor, and constitutes the legal, valid and
binding obligation of such Investor, enforceable against such Investor in
accordance with its terms, except as such enforceability may be limited by, or
subject to, any bankruptcy, insolvency, reorganization, moratorium or similar
laws affecting the enforcement of creditors' rights generally and subject to
general principles of equity.

        SECTION 3.4 Investment Representations.

                (a)     Such Investor acknowledges that the offer and sale of
the Shares to such Investor have not been registered under the Securities Act,
or the securities laws of any state or regulatory body, are being offered and
sold in reliance upon exemptions from the registration requirements of the
Securities Act and such laws and may not be transferred or resold without
registration under such laws unless an exemption is available. The certificates
representing the Shares will be imprinted with a legend in substantially the
following form:

                "THE OFFER AND SALE OF THE SECURITIES REPRESENTED BY THIS
                CERTIFICATE HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF
                1933, AS AMENDED, OR THE SECURITIES LAWS OF ANY STATE AND SUCH
                SECURITIES MAY NOT BE SOLD, TRANSFERRED, ASSIGNED, PLEDGED,
                HYPOTHECATED, OR OTHERWISE DISPOSED OF EXCEPT PURSUANT TO A
                REGISTRATION STATEMENT WITH RESPECT TO SUCH SECURITIES WHICH IS
                EFFECTIVE UNDER SUCH ACT AND UNDER ANY APPLICABLE STATE
                SECURITIES LAWS UNLESS, IN THE OPINION OF COUNSEL REASONABLY
                SATISFACTORY TO THE COMPANY, AN

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                EXEMPTION FROM THE REGISTRATION REQUIREMENTS OF SUCH ACT AND
                STATE SECURITIES LAWS IS AVAILABLE."

                (b)     Such Investor is acquiring the Shares for investment,
and not with a view to the resale or distribution thereof, and is acquiring such
Shares for its own account.

                (c)     Such Investor is an "accredited investor" (as that term
is defined in Rule 501 of Regulation D promulgated under the Securities Act), is
sophisticated in financial matters and is familiar with the business of the
Company so that it is capable of evaluating the merits and risks of its
investment in the Company and has the capacity to protect its own interests.
Such Investor has had the opportunity to investigate on its own the Company's
business, management and financial affairs and has had the opportunity to review
the Company's operations and facilities and to ask questions and obtain whatever
other information concerning the Company as such Investor has deemed relevant in
making its investment decision.

                (d)     Such Investor is in compliance with the Uniting and
Strengthening America by Providing Appropriate Tools Required to Intercept and
Obstruct Terrorism Act of 2001. Neither such Investor, nor any of its principal
owners, partners, members, directors or officers is included on: (i) the Office
of Foreign Assets Control list of foreign nations, organizations and individuals
subject to economic and trade sanctions, based on U.S. foreign policy and
national security goals; (ii) Executive Order 13224, which sets forth a list of
individuals and groups with whom U.S. persons are prohibited from doing business
because such persons have been identified as terrorists or persons who support
terrorism or (iii) any other watch list issued by any governmental authority,
including the Commission.

                (e)     No representations or warranties have been made to such
Investor by the Company or any director, officer, employee, agent or affiliate
of the Company, other than the representations and warranties of the Company set
forth herein, and the decision of such Investor to purchase the Shares is based
on the information contained herein, the Commission Filings and such Investor's
own independent investigation of the Company.

        SECTION 3.5 Governmental Consents. The execution and delivery by such
Investor of this Agreement, and the performance by such Investor of the
transactions contemplated hereby, do not and will not require such Investor to
effectuate or obtain any registration with, consent or approval of, or notice to
any federal state or other governmental authority or regulatory body, except for
the filing with the Commission of a Form 4 and an amendment to such Investor's
Schedule 13D under the Exchange Act with respect to its acquisition of the
Shares.

        SECTION 3.6 No Violation. The execution and delivery of this Agreement
and the performance by such Investor of the transactions contemplated hereby,
will not (i) conflict with or result in a breach of any provision of the
articles of incorporation, by-laws or similar organizational documents of such
Investor or (ii) violate any law, judgment, order, writ, injunction, decree,
statute, rule or regulation of any court, administrative agency, bureau, board,
commission, office, authority,

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department or other governmental entity applicable to such Investor, except, in
the case of clause (ii) above, any such violation that could not reasonably be
expected to materially impair the transactions contemplated hereby.

        SECTION 3.7 Brokers. Neither such Investor, nor any of its officers,
directors or employees, has employed any broker or finder, or incurred any
liability for any brokerage fees, commissions, finder's or other similar fees or
expenses in connection with the transactions contemplated hereby.

                                   ARTICLE IV
                            SURVIVAL; INDEMNIFICATION

        SECTION 4.1 Survival. The representations and warranties contained in
Articles II and III hereof shall survive until the first anniversary of the date
hereof.

        SECTION 4.2 Indemnification. Each party (including its officers,
directors, employees, affiliates, agents, successors and assigns (each an
"Indemnified Party")) shall be indemnified and held harmless by the other
parties hereto (each an "Indemnifying Party") for any and all liabilities,
losses, damages, claims, costs and expenses, interest, awards, judgments and
penalties (including, without limitation, reasonable attorneys' fees and
expenses) actually suffered or incurred by them (collectively, "Losses"),
arising out of or resulting from the breach of any representation or warranty
made by an Indemnifying Party contained in this Agreement. Notwithstanding the
foregoing, the aggregate liability of any Investor under this Article IV shall
in no event exceed fifty percent (50%) of the purchase price paid by such
Investor for the Shares purchased by it and the aggregate liability of the
Company under this Article IV shall in no event exceed fifty percent (50%) of
the purchase price paid by the Investors for the Shares, except that the
Company's liability for a violation of any of the representations and warranties
contained in the first two sentences of Section 2.7 may exceed such limitation,
but shall in no event exceed one hundred percent (100%) of the purchase price
paid by the Investors for the Shares.

        SECTION 4.3 Indemnification Procedure. The obligations and liabilities
of the Indemnifying Party under this Article IV with respect to Losses arising
from claims of any third party that are subject to the indemnification provided
for in this Article IV ("Third Party Claims") shall be governed by and
contingent upon the following additional terms and conditions: if an Indemnified
Party shall receive notice of any Third Party Claim, the Indemnified Party shall
give the Indemnifying Party notice of such Third Party Claim promptly after the
receipt by the Indemnified Party of such notice (which notice shall include the
amount of the Loss, if known, and method of computation thereof, and containing
a reference to the provisions of this Agreement in respect of which such right
of indemnification is claimed or arises); provided, however, that the failure to
provide such notice shall not release the Indemnifying Party from any of its
obligations under this Article IV except to the extent the Indemnifying Party is
materially prejudiced by such failure and shall not relieve the Indemnifying
Party from any other obligation or liability that it may have to any Indemnified
Party otherwise than under this Article IV. Upon written notice to the

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Indemnified Party within five (5) days of the receipt of such notice, the
Indemnifying Party shall be entitled to assume and control the defense of such
Third Party Claim at its or his expense and through counsel of its or his choice
(which counsel shall be reasonably satisfactory to the Indemnified Party);
provided, however, that, if there exists or is reasonably likely to exist a
conflict of interest that would make it inappropriate in the reasonable judgment
of counsel to the Indemnified Party for the same counsel to represent both the
Indemnified Party and the Indemnifying Party, then the Indemnified Party shall
be entitled to retain its or his own counsel in each jurisdiction for which the
Indemnified Party reasonably determines counsel is required, at the expense of
the Indemnifying Party. In the event the Indemnifying Party exercises the right
to undertake any such defense against any such Third Party Claim as provided
above, the Indemnified Party shall cooperate with the Indemnifying Party in such
defense and make available to such Indemnifying Party, at the Indemnifying
Party's expense, all witnesses, pertinent records, materials and information in
the Indemnified Party's possession or under the Indemnified Party's control
relating thereto as is reasonably required by the Indemnifying Party. Similarly,
in the event the Indemnified Party is, directly or indirectly, conducting the
defense against any such Third Party Claim, the Indemnifying Party shall
cooperate with the Indemnified Party in such defense and make available to the
Indemnified Party, at the Indemnifying Party's expense, all such witnesses
(including himself), records, materials and information in the Indemnifying
Party's possession or under the Indemnifying Party's control relating thereto as
is reasonably required by the Indemnified Party. No such Third Party Claim may
be settled by the Indemnifying Party on behalf of the Indemnified Party without
the prior written consent of the Indemnified Party (which consent shall not be
unreasonably withheld); provided, however, in the event that the Indemnified
Party does not consent to any such settlement that would provide it with a full
release from indemnified Loss and would not require it to take, or refrain from
taking, any action, the Indemnifying Party's liability for indemnification shall
not exceed the amount of such proposed settlement. The Indemnified Party will
refrain from any act or omission that is inconsistent with the position taken by
the Indemnifying Party in the defense of a Third Party Claim unless the
Indemnified Party determines that such act or omission is reasonably necessary
to protect its own interest.

                                    ARTICLE V
                                  MISCELLANEOUS

        SECTION 5.1 Change of Control Provision. For so long as any of the
Shares are owned by the Investors or their affiliates, the Company will not
agree to, or take any action to approve or otherwise facilitate any, merger or
consolidation or Change of Control (including granting approvals required under
applicable anti-takeover statutes), unless provision has been made for the
holders of the Shares to receive from the acquiror or any other person or entity
(other than the Company) as a result of and in connection with the transaction
an amount in cash equal to the aggregate liquidation preference for the Shares
held by them, as set forth in the Certificate of Powers, Designations,
Preferences and Rights of the Series E Preferred Stock. The parties hereto agree
that irreparable damage would occur in the event that the provisions of this
Section 5.1 were not performed in accordance with their terms and the Investors
shall be entitled to specific performance of the terms of this Section 5.1 in
addition to any other remedies at law or in equity.

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For purposes of this Section 5.1: a "Change of Control" shall mean any of the
following (i) any person or "group" (within the meaning of Section 13(d)(3) of
the Exchange Act) becoming the beneficial owner, directly or indirectly, of
outstanding shares of Capital Stock of the Company entitling such Person or
Persons to exercise 50% or more of the total votes entitled to be cast at a
regular or special meeting, or by action by written consent, of the shareholders
of the Company in the election of directors (the term "beneficial owner" shall
be determined in accordance with Rule 13d-3 of the Exchange Act), (ii) a
majority of the Board of Directors of the Company shall consist of Persons other
than Continuing Directors, (iii) a recapitalization, reorganization, merger,
consolidation or similar transaction, in each case with respect to which all or
substantially all the Persons who are the respective beneficial owners, directly
or indirectly, of the outstanding shares of Capital Stock of the Company
immediately prior to such recapitalization, reorganization, merger,
consolidation or similar transaction, will own less than 50% of the combined
voting power of the then outstanding shares of Capital Stock of the Company
resulting from such recapitalization, reorganization, merger, consolidation or
similar transaction, (iv) the sale or other disposition of all or substantially
all the assets of the Company in one transaction or in a series of related
transactions, (v) any transaction occurs (other than one described in (iv) or
(v))), the result of which is that the Common Stock is not required to be
registered under Section 12 of the Exchange Act and in which the holders of
Common Stock of the Company do not receive common stock of the Person surviving
such transaction which is required to be registered under Section 12 of the
Exchange Act, or (vi) immediately after any merger, consolidation,
recapitalization or similar transaction, a "group" (within the meaning of
Section 13(d)(3) of the Exchange Act), other than a group that includes the
Investors and/or their affiliates, shall be the beneficial owners, directly or
indirectly, of outstanding shares of Capital Stock of the Company (or any Person
surviving such transaction) entitling them collectively to exercise 50% or more
of the total voting power of shares of Capital Stock of the Company (or the
surviving Person in such transaction) and in connection with or as a result of
such transaction, the Company (or such surviving Person) shall have incurred or
issued additional indebtedness such that the total indebtedness so incurred or
issued equals at least 50% of the consideration payable in such transaction;
"Capital Stock" shall mean, with respect to the Company, any and all shares,
interests, participations, rights in, or other equivalents (however designated
and whether voting or non-voting) of, the Company's capital stock; and "Person"
shall mean any individual, firm, corporation, partnership, limited liability
company, trust, incorporated or unincorporated association, joint venture, joint
stock company, governmental authority or other entity of any kind, and shall
include any successor (by merger or otherwise) of such entity; and "Continuing
Directors" shall mean any member of the Board of Directors on the date hereof
and any other member of the Board of Directors who shall be recommended or
elected to succeed or become a Continuing Director by a majority of the
Continuing Directors who are then members of the Board of Directors.

        SECTION 5.2 Registrable Securities. The shares of Common Stock issuable
upon the conversion of the Shares (the "New Registrable Securities") shall be
deemed "Registrable Securities" under the terms of the Investment Agreement by
and among the Company, the Company's predecessor and the Investors, dated
November 13, 2000 (the "Series B Investment Agreement") (subject to the
provisions of Section 13.1(a) of the Series B Investment Agreement),

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and the parties hereto (who also constitute all of the parties to the Series B
Investment Agreement) hereby amend the definition of "Registrable Securities"
contained in the Series B Investment Agreement so that such definition includes
the New Registrable Securities, along with any other securities already included
within the definition thereof.

        SECTION 5.3 Stockholder Approval. The Company shall put forth proposals
at its next annual or special meeting of stockholders seeking approval of the
conversion rights of the Series E Preferred Stock. The Company shall take all
reasonable action to convene a meeting of stockholders of the Company to be held
on or before December 31, 2003 to approve the foregoing matters.

        SECTION 5.4 Publicity. Except as may be required by applicable law or
the rules of any securities exchange or market on which securities of the
Company are traded, no party hereto shall issue a press release or public
announcement or otherwise make any disclosure concerning this Agreement and the
transactions contemplated hereby, without prior approval of the others;
provided, however, that nothing in this Agreement shall restrict the Company or
any Investor from disclosing such information (a) that is already publicly
available, (b) that may be required or appropriate in response to any summons or
subpoena (provided that the disclosing party will use commercially reasonable
efforts to notify the other parties in advance of such disclosure under this
clause (b) so as to permit the non-disclosing parties to seek a protective order
or otherwise contest such disclosure, and the disclosing party will use
commercially reasonable efforts to cooperate, at the expense of the
non-disclosing parties, in pursuing any such protective order) or (c) in
connection with any litigation involving disputes as to the parties' respective
rights and obligations hereunder.

        SECTION 5.5 Entire Agreement. This Agreement and any other agreement or
instrument to be delivered expressly pursuant to the terms hereof constitute the
entire Agreement between the parties hereto with respect to the subject matter
hereof and supersede all previous negotiations, commitments and writings with
respect to such subject matter.

        SECTION 5.6 Assignments; Parties in Interest. Neither this Agreement nor
any of the rights, interests or obligations hereunder may be assigned by any of
the parties hereto (whether by operation of law or otherwise) without the prior
written consent of the other parties. This Agreement shall be binding upon and
inure solely to the benefit of each party hereto, and nothing herein, express or
implied, is intended to or shall confer upon any person not a party hereto any
right, benefit or remedy of any nature whatsoever under or by reason hereof,
except as otherwise provided herein.

        SECTION 5.7 Amendments. This Agreement may not be amended or modified
except by an instrument in writing signed by, or on behalf of, the parties
against whom such amendment or modification is sought to be enforced.

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        SECTION 5.8 Descriptive Headings. The descriptive headings of this
Agreement are inserted for convenience of reference only and do not constitute a
part of and shall not be utilized in interpreting this Agreement.

        SECTION 5.9 Notices and Addresses. Any notice, demand, request, waiver,
or other communication under this Agreement shall be in writing and shall be
deemed to have been duly given on the date of service, if personally served or
sent by facsimile; on the business day after notice is delivered to a courier or
mailed by express mail, if sent by courier delivery service or express mail for
next day delivery; and on the fifth business day after mailing, if mailed to the
party to whom notice is to be given, by first class mail, registered, return
receipt requested, postage prepaid and addressed as follows:

To Company:     Bluefly, Inc.
                42 West 39th Street, 9th Floor
                New York, New York 10018
                Fax:   (212) 840-1903
                Attn:  Jonathan B. Morris

                With a copy to:

                Swidler Berlin Shereff Friedman, LLP
                405 Lexington Avenue
                New York, New York 10174
                Fax:   (212) 891-9598
                Attn:  Richard A. Goldberg, Esq.

To the Investors: To the address set forth on Schedule 1.

        SECTION 5.10 Severability. In the event that any provision of this
Agreement becomes or is declared by a court of competent jurisdiction to be
illegal, void or unenforceable, the remainder of this Agreement will continue in
full force and effect and the application of such provision to other persons or
circumstances will be interpreted so as reasonably to effect the intent of the
parties hereto. The parties further agree to replace such void or unenforceable
provision of this Agreement with a valid and enforceable provision that will
achieve, to the extent possible, the economic, business and other purposes of
such void or unenforceable provision.

        SECTION 5.11 Governing Law. This Agreement shall be governed by and
construed in accordance with the internal laws of the State of New York, without
regard to conflicts of law principles. The parties agree that the federal and
state courts located in New York, New York shall have exclusive jurisdiction
over any dispute involving this Agreement or the transactions contemplated
hereby, and each party hereby irrevocably submits to the jurisdiction of, and
waives any objection to the laying of venue in, such courts.

                                       11
<PAGE>

        SECTION 5.12 Counterparts; Facsimile Signatures. This Agreement may be
executed in one or more counterparts, all of which shall be considered one and
the same agreement and shall become effective when one or more counterparts have
been signed by each of the parties and delivered to the other parties, it being
understood that all parties need not sign the same counterpart. This Agreement
may be executed by facsimile, and a facsimile signature shall have the same
force and effect as an original signature on this Agreement.

        SECTION 5.13 Expenses. The Company shall reimburse the Investors for
their reasonable legal fees and expenses incurred in connection with the
negotiation of this Agreement and the transactions contemplated hereby. Except
as provided above, all costs and expenses, including, without limitation, fees
and disbursements of counsel, incurred in connection with the negotiation,
execution and delivery of this Agreement and its related documents shall be paid
by the party incurring such costs and expenses, whether or not the closing shall
have occurred.

                                       12
<PAGE>

        IN WITNESS WHEREOF, this Agreement has been duly executed on the date
first set forth above.

                                           BLUEFLY, INC.

                                           By:  /s/ Jonathan B. Morris
                                                ------------------------------
                                                Name:  Jonathan B. Morris
                                                Title: Executive Vice President


                                           QUANTUM INDUSTRIAL PARTNERS LDC

                                           By:  /s/ John F. Brown
                                                ------------------------------
                                                Name:  John F. Brown
                                                Title: Attorney-in-fact


                                           SFM DOMESTIC INVESTMENTS LLC

                                           By:  /s/ John F. Brown
                                                ------------------------------
                                                Name:  John F. Brown
                                                Title: Attorney-in-fact

                                       13
<PAGE>

                                                                   EXHIBIT 10.53

                                   SCHEDULE 1

                         INVESTORS AND SHARE ALLOCATIONS

<TABLE>
<CAPTION>
NAME AND ADDRESS OF INVESTOR           SHARES PURCHASED    AGGREGATE PURCHASE PRICE FOR SHARES PURCHASED
-------------------------------------  ----------------    ---------------------------------------------
<S>                                          <C>                            <C>
Quantum Industrial Partners LDC              968.3                          $    968,300
Kaya Flamboyan 9
Villemstad
Curacao
Netherlands-Antilles

with a copy to:

Soros Fund Management LLC
888 Fifth Avenue
New York, New York 10106
Facsimile:  (212) 664-0544
Attn:  John F. Brown, Esq.

SFM Domestic Investments LLC                  31.7                          $     31,700
c/o Soros Fund Management LLC
888 Fifth Avenue
New York, New York 10106
Facsimile:  (212) 664-0544
Attn:  John F. Brown, Esq.
--------------------------------------------------------------------------------------------------------
                             TOTAL           1,000                          $  1,000,000
--------------------------------------------------------------------------------------------------------
</TABLE>

<PAGE>

                                                                   EXHIBIT 10.53

                                  SCHEDULE 2.4

                                 CAPITALIZATION

        As of the date hereof, but without giving effect to the transactions
contemplated by this Agreement, the following equity securities are outstanding
and convertible into, or exercisable for shares of Common Stock:

        1.      460,000 shares of Series A Convertible Preferred Stock (the
                "Series A Stock") are issued and outstanding. The Series A Stock
                is convertible into 3,931,624 shares of Common Stock.

        2.      8,889,414 shares of Series B Convertible Preferred Stock (the
                "Series B Stock") are issued and outstanding. The Series B Stock
                is convertible into 27,370,038 shares of Common Stock.

        3.      Warrants to purchase an aggregate of 1,119,144 shares of Common
                Stock are issued and outstanding.

        4.      Options issued to purchase 9,582,912 shares of Common Stock are
                issued and outstanding under the Company's 1997 Stock Option
                Plan, as amended, and 2000 Stock Option Plan, as amended.

        5.      1,000 shares of Series C Convertible Preferred Stock (the
                "Series C Stock") are issued and outstanding. The Series C Stock
                is convertible into 1,315,788 shares of Common Stock.

        6.      7,136.548 Shares of Series D Convertible Preferred Stock (the
                "Series D Stock") are issued and outstanding. The Series D Stock
                is convertible into 9,390,194 shares of Common Stock.