                                                                     Exhibit 5.1

August 24, 2006

Bluefly, Inc.
42 West 39th Street, 9th Floor
New York, NY 10018

Ladies and Gentlemen:

         On the date hereof, Bluefly, Inc., a Delaware corporation (the
"Company"), intends to file with the Securities and Exchange Commission (the
"Commission") a Registration Statement on Form S-3 (the "Registration
Statement"), relating to the resale by certain stockholders of the Company of
110,665,647 shares (the "Shares") of the Company's common stock, par value $0.01
per share (the "Common Stock"), and 706,644 shares of the Company's Common Stock
issuable upon exercise of outstanding warrants to purchase Common Stock (the
"Warrant Shares" and, together with the Shares, the "Registered Shares"). This
opinion is an exhibit to the Registration Statement.

         We have acted as special counsel to the Company in connection with
certain corporate and securities matters, and in such capacity we are familiar
with the various corporate and other proceedings relating to the proposed offer
and sale of the Registered Shares as contemplated by the Registration Statement.

         In rendering the opinions set forth herein, we have examined executed
originals, counterparts or copies of executed originals or counterparts of each
of the documents referenced below:

         (a)      the stock purchase, subscription and other agreements pursuant
to which the Shares were issued;

         (b)      the agreements evidencing the warrants pursuant to which the
Warrant Shares will be issued;

         (c)      the Company's Certificate of Incorporation, as presently in
effect (the "Certified Charter");

         (d)      the Company's Bylaws, as presently in effect (together with
the Certified Charter, collectively, the "Certified Organizational Documents");
and

         (e)      the minutes and other instruments (the "Minutes") evidencing
actions taken by the Company's directors.

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Bluefly, Inc.
August 24, 2006
Page 2

         As to certain factual matters related to this opinion letter, we have
relied upon the certificate of an officer of the Company.

         In rendering the opinions set forth herein, we have assumed, without
independent verification or inquiry, the following:

                  (i)      the authenticity of all documents submitted to us as
originals;

                  (ii)     the conformity to original documents of all documents
submitted to us as certified, conformed or photostatic copies;

                  (iii)    the genuineness of all signatures;

                  (iv)     insofar as this opinion relates to securities to be
issued in the future, we have assumed that all applicable laws, rules and
regulations in effect at the time of such issuance will be the same as such
laws, rules and regulations in effect as of the date hereof; and

                  (v)      that the Company has received consideration for the
issuance of the Registered Shares (other than the Warrant Shares).

         Our opinion herein is based solely upon the General Corporation Law of
the State of Delaware, and we express no opinion with respect to any other laws
(including, without limitation, the application of the securities or "blue sky"
laws of any state to the offer and/or sale of the Registered Shares).

         Based on the foregoing, and subject to and in reliance upon the
accuracy and completeness of the information relevant thereto provided to us, it
is our opinion that, subject to the effectiveness of the Registration Statement
and compliance with applicable state laws, including securities laws, (i) the
Registered Shares (other than the Warrant Shares) have been legally issued and
are fully paid and non-assessable, and (ii) the Warrant Shares, when issued and
paid for in accordance with the terms of the applicable warrant, will be legally
issued, fully paid and non-assessable.

         We hereby consent to the filing of this opinion as an exhibit to the
Registration Statement and as an exhibit to any filing made by the Company under
the securities or other laws of any state of the United States in which the
Registered Shares may be offered and sold. In giving such consent, we do not
thereby admit that we are in the category of persons whose consent is required
under Section 7 of the Securities Act of 1933, as amended, or the rules and
regulations of the Commission.

         This opinion is furnished to you in connection with the filing of the
Registration Statement, and is not to be used, circulated, quoted or otherwise
relied upon for any other purpose, except as expressly provided in the preceding

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Bluefly, Inc.
August 24, 2006
Page 3

paragraph, without our express written consent. This opinion is rendered to you
as of the date hereof, and we undertake no obligation to advise you of any
change in any applicable law or in facts or circumstances which might affect any
matters or opinions set forth herein.


                                                              Very truly yours,

                                                              /s/ Dechert LLP

                                                              DECHERT LLP
