Exhibit 10.5


 


THE SECURITIES REPRESENTED BY THIS CERTIFICATE
HAVE NOT BEEN REGISTERED, QUALIFIED, APPROVED OR DISAPPROVED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES
ACT”), OR THE SECURITIES LAWS OF ANY STATE AND MAY NOT BE SOLD OR OTHERWISE DISPOSED OF EXCEPT PURSUANT TO AN EFFECTIVE
REGISTRATION STATEMENT UNDER THE SECURITIES ACT AND APPLICABLE STATE SECURITIES LAWS OR AN APPLICABLE EXEMPTION FROM THE REGISTRATION
REQUIREMENTS UNDER SUCH ACT OR LAWS AND NEITHER THE SECURITIES AND EXCHANGE COMMISSION NOR ANY OTHER FEDERAL OR STATE REGULATORY
AUTHORITY HAS PASSED ON OR ENDORSED THE MERITS OF THESE SECURITIES.


 


WARRANT NO. 2


 


WARRANT


 


TO PURCHASE SHARES OF COMMON STOCK


 


OF


 


BLUEFLY, INC.


 


THIS IS TO CERTIFY THAT
RHO VENTURES VI, L.P., a Delaware limited partnership, or its registered assigns (the “Holder”), is the owner
of the right to subscribe for and to purchase from BLUEFLY, INC., a Delaware corporation (the “Company”), Four
Hundred Seventy Six Thousand One Hundred Ninety (476,190) (the “Number Issuable”), fully paid, duly authorized
and non-assessable shares of Common Stock at a price per share of $1.05 (the “Exercise Price”), at any time,
in whole or in part, on or after August 13, 2012 (the “Effective Date”) through 5:00 PM New York City time, on August
13, 2019 (the “Expiration Date”) all on the terms and subject to the conditions hereinafter set forth (the “Warrants”).


 


The Number Issuable and
the Exercise Price are subject to further adjustment from time to time pursuant to the provisions of Section 2 of this Warrant
Certificate.


 


Capitalized terms used
herein but not otherwise defined shall have the meanings given to them in Section 12 hereof.


 


Section 1.         Exercise
of Warrants.


 


(a)         Subject
to paragraphs (d) and (e) of this Section 1, the Warrants evidenced hereby may be exercised, in whole or in part, by the Holder
hereof at any time or from time to time, on or after the Effective Date and on or prior to the Expiration Date upon delivery to
the Company at the principal executive office of the Company in the United States of America, of (A) this Warrant Certificate,
(B) a written notice stating that such Holder elects to exercise the Warrants evidenced hereby in accordance with the provisions
of this Section 1 and specifying the number of Warrants being exercised and the name or names in which the Holder wishes the certificate
or


 






    	 



    	 



    
 


certificates
for shares of Common Stock to be issued and (C) payment of the Exercise Price for such Warrants, which shall be payable by any
one or any combination of the following: (i) cash; (ii) certified or official bank check payable to the order of the Company;
(iii) by the surrender (which surrender shall be evidenced by cancellation of the number of Warrants represented by any Warrant
Certificate presented in connection with a Cashless Exercise (as defined below)) of a Warrant or Warrants (represented by one
or more relevant Warrant Certificates), and without the payment of the Exercise Price in cash, in return for the delivery to the
surrendering Holder of such number of shares of Common Stock equal to the number of shares of the Common Stock for which such
Warrant is exercisable as of the date of exercise (if the Exercise Price were being paid in cash or certified or official bank
check) reduced by that number of shares of Common Stock equal to the quotient obtained by dividing (x) the aggregate Exercise
Price (assuming no Cashless Exercise) to be paid by (y) the Market Price of one Share of Common Stock on the Business Day which
immediately precedes the day of exercise of the Warrant; or (iv) by the delivery of shares of the Common Stock having a value
(as defined by the next sentence) equal to the aggregate Exercise Price to be paid, that are either held by the Holder or are
acquired in connection with such exercise, and without payment of the Exercise Price in cash. Any share of Common Stock delivered
as payment for the Exercise Price in connection with an In-Kind Exercise (as defined below) shall be deemed to have a value equal
to the Market Price of one Share of Common Stock on the Business Day that immediately precedes the day of exercise of the Warrants.
An exercise of a Warrant in accordance with clause (iii) is herein referred to as a “Cashless Exercise” and
an exercise of a Warrant in accordance with clause (iv) is herein referred to as an “In-Kind Exercise.” The
documentation and consideration, if any, delivered in accordance with subsections (A), (B) and (C) are collectively referred to
herein as the “Warrant Exercise Documentation.”


 


(b)         As
promptly as practicable, and in any event within five (5) Business Days after receipt of the Warrant Exercise Documentation, the
Company shall deliver or cause to be delivered (A) certificates representing the number of validly issued, fully paid and nonassessable
shares of Common Stock specified in the Warrant Exercise Documentation, (B) if applicable, cash in lieu of any fraction of a share,
as hereinafter provided, and (C) if less than the full number of Warrants evidenced hereby are being exercised or used in a Cashless
Exercise, a new Warrant Certificate or Certificates, of like tenor, for the number of Warrants evidenced by this Warrant Certificate,
less the number of Warrants then being exercised and/or used in a Cashless Exercise. Such exercise shall be deemed to have been
made at the close of business on the date of delivery of the Warrant Exercise Documentation so that the Person entitled to receive
shares of Common Stock upon such exercise shall be treated for all purposes as having become the record holder of such shares of
Common Stock at such time.


 


(c)         The
Company shall pay all expenses incurred by the Company in connection with and taxes and other governmental charges (other than
income taxes of the Holder) that may be imposed in respect of, the issue or delivery of any shares of Common Stock issuable upon
the exercise of the Warrants evidenced hereby. The Company shall not be required, however, to pay any tax or other charge imposed
in


 






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connection
with any transfer involved in the issue of any certificate for shares of Common Stock, as the case may be, in any name other than
that of the registered holder of the Warrant evidenced hereby.


 


(d)         In
connection with the exercise of any Warrants evidenced hereby, no fractions of shares of Common Stock shall be issued, but in lieu
thereof the Company shall pay a cash adjustment in respect of such fractional interest in an amount equal to such fractional interest
multiplied by the Market Price for one Share of Common Stock on the Business Day which immediately precedes the day of exercise.
If more than one (1) such Warrant shall be exercised by the holder thereof at the same time, the number of full shares of Common
Stock issuable on such exercise shall be computed on the basis of the total number of Warrants so exercised.


 


(e)         Notwithstanding
anything to the contrary contained herein, the Holder and the Company acknowledge and agree that these Warrants shall not become
exercisable until the Stockholder Approval has been obtained. The Company shall take such actions as are reasonably necessary to
obtain the Stockholder Approval through an action by majority written consent of the stockholders in accordance with Section
1.3 of that certain Note and Warrant Purchase Agreement, dated as of the date hereof, by and among the Company, the Holder and
Prentice Consumer Partners, LP. “Stockholder Approval” means such approval of the
stockholders of the Company as may be necessary under the rules of the NASDAQ Capital Market or any other national securities exchange
or quotation system upon which the Common Stock may be listed from time to time, in order to permit the exercise in full of the
Warrants.


 


Section 2.         Certain
Adjustments.


 


(a)         The
number of shares of Common Stock purchasable upon the exercise of this Warrant and the Exercise Price shall be subject to adjustment
as follows:


 


(i)         Stock
Dividends, Subdivision, Combination or Reclassification of Common Stock.
If at any time after the date of the issuance of this Warrant the Company shall (i) pay a dividend on Common Stock in shares of
its capital stock, (ii) combine its outstanding shares of Common Stock into a smaller number of shares, (iii) subdivide its outstanding
shares of Common Stock as the case may be, or (iv) issue by reclassification of its shares of Common Stock any shares of capital
stock of the Company, then, on the record date for such dividend or the effective date of such subdivision or split-up, combination
or reclassification, as the case may be, the number and kind of shares to be delivered upon exercise of this Warrant will be adjusted
so that the Holder will be entitled to receive the number and kind of shares of capital stock that such Holder would have owned
or been entitled to receive upon or by reason of such event had this Warrant been exercised immediately prior thereto, and the
Exercise Price will be adjusted as provided below in paragraph 2(a)(v).


 


(ii)         Extraordinary
Distributions. If at any time after the date of issuance of this Warrant, the Company shall distribute to all holders of Common
Stock


 






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(including
any such distribution made in connection with a consolidation or merger in which the Company is the continuing or surviving corporation
and Common Stock is not changed or exchanged) cash, evidences of indebtedness, securities or other assets (excluding (A) ordinary
course cash dividends to the extent such dividends do not exceed the Company’s retained earnings and (B) dividends payable
in shares of capital stock for which adjustment is made under Section 2(a)(i)), or rights, options or warrants to subscribe for
or purchase securities of the Company, then in each such case the number of shares of Common Stock to be delivered to such Holder
upon exercise of this Warrant shall be increased so that the Holder thereafter shall be entitled to receive the number of shares
of Common Stock determined by multiplying the number of shares such Holder would have been entitled to receive immediately before
such record date by a fraction, the denominator of which shall be the Exercise Price on such record date minus the then fair market
value (as reasonably determined by the Board of Directors of the Company in good faith) of the portion of the cash, evidences
of indebtedness, securities or other assets so distributed or of such rights or warrants applicable to one share of the Common
Stock (provided that such denominator shall in no event be less than $.01) and the numerator of which shall be the Exercise Price.


 


(iii)         Reorganization,
etc. If at any time after the date of issuance of this Warrant any consolidation of the Company with or merger of the Company
with or into any other Person (other than a merger or consolidation in which the Company is the surviving or continuing corporation
and which does not result in any reclassification of, or change (other than a change in par value or from par value to no par value
or from no par value to par value, or as a result of a subdivision or combination) in, outstanding shares of Common Stock) or any
sale, lease or other transfer of all or substantially all of the assets of the Company to any other person (each, a “Reorganization
Event”), shall be effected in such a way that the holders of the Common Stock shall be entitled to receive cash, stock,
other securities or assets (whether such cash, stock, other securities or assets are issued or distributed by the Company or another
Person) with respect to or in exchange for the Common Stock, then this Warrant shall automatically become exercisable only for
the kind and amount of cash, stock, other securities or assets receivable upon such Reorganization Event by a holder of the number
of shares of the Common Stock that such holder would have been entitled to receive upon exercise of this Warrant had this Warrant
been exercised immediately before such Reorganization Event, subject to adjustments that shall be as nearly equivalent as may be
practicable to the adjustments provided for in this Section 2(a). The Company shall not enter into any of the transactions referred
to in this Section 2(a)(iii) unless effective provision shall be made so as to give effect to the provisions set forth in this
Section 2(a)(iii).


 


(iv)         Carryover.
Notwithstanding any other provision of this Section 2(a), no adjustment shall be made to the number of shares of either Common
Stock to be delivered to the Holder (or to the Exercise Price) if such adjustment represents less than .05% of the number of shares
to be so delivered, but any lesser adjustment shall be carried forward and shall be made at the time and together with the next
subsequent adjustment that together with any adjustments so carried forward shall amount to .05% or more of the number of shares
to be so delivered.


 






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(v)         Exercise
Price Adjustment. Whenever the Number Issuable upon the exercise of the Warrant is adjusted as provided pursuant to this Section
2(a), the Exercise Price per share payable upon the exercise of this Warrant shall be adjusted by multiplying such Exercise Price
immediately prior to such adjustment by a fraction, of which the numerator shall be the Number Issuable upon the exercise of the
Warrant immediately prior to such adjustment, and of which the denominator shall be the Number Issuable immediately thereafter;
provided, however, that the Exercise Price for each Share of the Common Stock shall in no event be less than the par value of a
share of such Common Stock.


 


(b)         Notice
of Adjustment. Whenever the Number Issuable or the Exercise Price is adjusted as herein provided, the Company shall promptly
mail by first class mail, postage prepaid, to the Holder, notice of such adjustment or adjustments setting forth the Number Issuable
and the Exercise Price after such adjustment, setting forth a brief statement of the facts requiring
such adjustment and setting forth the computation by which such adjustment was made.


 


Section 3.         No
Redemption. The Company shall not have any right to redeem any of the Warrants evidenced hereby.


 


Section 4.         Notice
of Certain Events. In case at any time or from time to time (i) the Company shall declare
any dividend or any other distribution to all holders of Common Stock, (ii) the Company shall authorize the granting to the holders
of Common Stock of rights or warrants to subscribe for or purchase any additional shares of stock of any class or any other right,
(iii) the Company shall authorize the issuance or sale of any other shares or rights which would result in an adjustment to the
Number Issuable pursuant to Section 2(a)(i), (ii) or (iii), (iv) there shall be any capital reorganization or reclassification
of Common Stock of the Company or consolidation or merger of the Company with or into another Person, or any sale or other disposition
of all or substantially all the assets of the Company, or (v) there shall be a voluntary or involuntary dissolution, liquidation
or winding up of the Company, then, in any one or more of such cases the Company shall mail to the Holder at such Holder’s
address as it appears on the transfer books of the Company, as promptly as practicable but in any event at least 10 days prior
to the date on which the transactions contemplated in Section 2(a)(i), (ii) or (iii) a notice stating (a) the date on which a record
is to be taken for the purpose of such dividend, distribution, rights or warrants or, if a record is not to be taken, the date
as of which the holders of record of either Common Stock to be entitled to such dividend, distribution, rights or warrants are
to be determined, or (b) the date on which such reclassification, consolidation, merger, sale, conveyance, dissolution, liquidation
or winding up is expected to become effective. Such notice also shall specify the date as of which it is expected that the holders
of record of the Common Stock shall be entitled to exchange the Common Stock for shares of stock or other securities or property
or cash deliverable upon such reorganization, reclassification, consolidation, merger, sale, conveyance, dissolution, liquidation
or winding up.


 






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Section 5.         Certain
Covenants. The Company covenants and agrees that all shares of Common Stock of
the Company which may be issued upon the exercise of the Warrants evidenced hereby will be duly authorized, validly issued and
fully paid and nonassessable. The Company shall at all times reserve and keep available for issuance upon the exercise of the Warrants,
such number of its authorized but unissued shares of Common Stock as will from time to time be sufficient to permit the exercise
of all outstanding Warrants, and shall take all action required to increase the authorized number of shares of Common Stock if
at any time there shall be insufficient authorized but unissued shares of Common Stock to permit such reservation or to permit
the exercise of all outstanding Warrants.


 


Section 6.         Registered
Holder. The persons in whose names this Warrant Certificate is registered shall be deemed
the owner hereof and of the Warrants evidenced hereby for all purposes. The registered Holder of this Warrant Certificate, in their
capacity as such, shall not be entitled to any rights whatsoever as a stockholder of the Company, except as herein provided.


 


Section 7.         Transfer
of Warrants. Any transfer of the rights represented by this Warrant Certificate shall be effected by the surrender of this
Warrant Certificate, along with the form of assignment attached hereto, properly completed and executed by the registered Holder
hereof, at the principal executive office of the Company in the United States of America, together with an appropriate investment
letter and opinion of counsel, if deemed reasonably necessary by counsel to the Company to assure compliance with applicable securities
laws. Thereupon, the Company shall issue in the name or names specified by the registered Holder hereof and, in the event of a
partial transfer, in the name of the registered Holder hereof, a new Warrant Certificate or Certificates evidencing the right to
purchase such number of shares of Common Stock as shall be equal to the number of shares of Common Stock then purchasable hereunder.


 


Section 8.         Denominations.
The Company covenants that it will, at its expense, promptly upon surrender of this Warrant Certificate at the principal executive
office of the Company in the United States of America, execute and deliver to the registered Holder hereof a new Warrant Certificate
or Certificates in denominations specified by such Holder for an aggregate number of Warrants equal to the number of Warrants evidenced
by this Warrant Certificate.


 


Section 9.         Replacement
of Warrants. Upon receipt of evidence satisfactory to the Company of the loss, theft, destruction or mutilation of this
Warrant Certificate and, in the case of loss, theft or destruction, upon delivery of an indemnity reasonably satisfactory to the
Company (in the case of an insurance company or other institutional investor, its own unsecured indemnity agreement shall be deemed
to be reasonably satisfactory), or, in the case of mutilation, upon surrender and cancellation thereof, the Company will issue
a new Warrant Certificate of like tenor for a number of Warrants equal to the number of Warrants evidenced by this Warrant Certificate.


 






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Section 10.         Governing
Law. THIS WARRANT CERTIFICATE SHALL BE CONSTRUED AND ENFORCED IN ACCORDANCE WITH, AND THE RIGHTS OF THE PARTIES SHALL
BE GOVERNED BY, THE LAWS OF THE STATE OF NEW YORK APPLICABLE TO AGREEMENTS MADE AND TO BE PERFORMED ENTIRELY WITHIN SUCH STATE.


 


Section 11.         Rights
Inure to Registered Holder. The Warrants evidenced by this Warrant Certificate will inure to the benefit of and be binding
upon the registered Holder thereof and the Company and their respective successors and permitted assigns. Nothing in this Warrant
Certificate shall be construed to give to any Person other than the Company and the registered Holder thereof any legal or equitable
right, remedy or claim under this Warrant Certificate, and this Warrant Certificate shall be for the sole and exclusive benefit
of the Company and such registered Holder. Nothing in this Warrant Certificate shall be construed to give the registered Holder
hereof any rights as a Holder of shares of either Common Stock until such time, if any, as the Warrants evidenced by this Warrant
Certificate are exercised in accordance with the provisions hereof.


 


Section 12.         Definitions.
For the purposes of this Warrant Certificate, the following terms shall have the meanings indicated below:


 


“Business
Day” means any day other than a Saturday, Sunday or other day on which commercial banks in the City of New York, New
York are authorized or required by law or executive order to close.


 


“Capital Stock”
of any Person means any and all shares, interests, participations or other equivalents (however designated) of such Person’s
capital stock (or equivalent ownership interests in a Person not a corporation) whether now outstanding or hereafter issued, including,
without limitation, any rights, warrants or options to purchase such Person’s capital stock.


 


“Common Stock”
shall mean the common stock of the Company.


 


“Market Price”
shall mean, per share of Common Stock, on any date specified herein: (i) if the shares of Common Stock are traded on the NASDAQ
Capital Market, the last bid price reported on that date; (ii) if the shares of Common Stock are no longer quoted on NASDAQ Capital
Market and are listed on any other national securities exchange, the last sale price of the Common Stock reported by such exchange
on that date; (iii) if the shares of Common Stock are not quoted on a any such market or listed on any such exchange and the shares
of Common Stock are traded in the over-the-counter market, the last price reported on such day by the OTC Bulletin Board; (iv)
if the shares of Common Stock are not quoted on any such market, listed on any such exchange or quoted on the OTC Bulletin Board,
then the last price quoted on such day in the over-the-counter market as reported by the National Quotation Bureau Incorporated
(or any similar organization or agency succeeding its functions of


 






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reporting
prices); or (v) if none of clauses (i)-(iv) are applicable, then as determined, in good faith, by the Board of Directors of the
Company.


 


“Person”
shall mean any individual, corporation, limited liability company, partnership, trust, incorporated or unincorporated association,
joint venture, joint stock company, government (or an agency or political subdivision thereof) or other entity of any kind.


 


Section
13.         Notices. All notices, demands and other communications
provided for or permitted hereunder shall be made in writing and shall be by registered or certified first-class mail, return receipt
requested, courier services or personal delivery, (a) if to the Holder of a Warrant, at such Holder’s last known address
appearing on the books of the Company; and (b) if to the Company, at its principal executive office in the United States, or such
other address as shall have been furnished to the party given or making such notice, demand or other communication. All such notices
and communications shall be deemed to have been duly given: (i) when delivered by hand, if personally
delivered; (ii) when delivered to a courier if delivered by commercial overnight courier service; and (iii) five (5) Business Days
after being deposited in the mail, postage prepaid, if mailed.


 


[Signature Page Follows]


 






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IN WITNESS WHEREOF,
the Company has caused this Warrant Certificate to be duly executed as of this 13th day of August 2012.


  














	 	BLUEFLY, INC.	 
	 	 	 	 
	 	By:	/ s / Joseph Park	 
	 	Name:	Joseph Park	 
	 	Title:	CEO	 


 





ACCEPTED AND AGREED TO


AS OF AUGUST 13, 2012:


 


	RHO VENTURES VI, L.P.


 


By: RMV VI, L.L.C., its General Partner


 


By: Rho Capital Partners LLC, its Managing Member


	 	 	 	 
	 	 	 	 
	By: 	/ s / Jeffrey Martin	 	 
	Name:	Jeffrey Martin	 	 
	Title:	Attorney-in-fact	 	 


 






    	Signature Page to Rho Warrant



    	 



    
 


[Form of Assignment Form]


 


[To be executed upon assignment of Warrants]


 





The undersigned hereby
assigns and transfers this Warrant Certificate to _______________ whose Social Security Number or Tax ID Number is ____________________________
and
whose record address is


, and irrevocably appoints ____________________________


 


as agent to transfer this security on the
books of the Company. Such agent may substitute another to act for such agent.


 





	 	Signature:	 
	 	 	 
	 	 	 
	 	Signature Guarantee:	 
	 	 	 
	 	 	 
	 	 	 


 


Date: _________________