

                                                                     Exhibit 5.1

                           [Letterhead of Dechert LLP]

October 16, 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.1 to Form S-3, File No. 333-136866 (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. We will, however, update this opinion as of the date of effectiveness of
the Registration Statement.

                                                              Very truly yours,

                                                              /s/ Dechert LLP

                                                              DECHERT LLP

