                                                                     Exhibit 5.1

                           [Letterhead of Dechert LLP]

October 18, 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")  Amendment  No.  2 to 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.

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

<PAGE>

         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; and

               (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.

         Our  opinion  is  limited  to  applicable  provisions  of the  Delaware
Constitution and the General Corporation Law of the State of Delaware ("Delaware
Law") and published judicial decisions  interpreting Delaware Law. 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.

         The opinion  expressed herein is rendered pursuant to Item 601(b)(5)(i)
of Regulation  S-K under the  Securities  Act and may not be used or relied upon
for any other purpose.

         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 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
