Document:

EXHIBIT 10.8
                                                                    ------------

                       PREFERRED STOCK PURCHASE AGREEMENT

         THIS PREFERRED STOCK PURCHASE AGREEMENT (this "AGREEMENT") is made
effective this 26th day of April, 2007, by and between RonHow, LLC, a Georgia
limited liability company ("RONHOW"), and Harold's Stores, Inc., an Oklahoma
corporation (the "COMPANY"), with reference to the following circumstances:

         A. RonHow and the Company previously entered into that certain
Subordinated Loan Agreement dated August 31, 2006, as amended of even date
herewith (the "SUBORDINATED LOAN AGREEMENT"), pursuant to which the Company and
certain of its subsidiaries (collectively, the "BORROWERS") may borrow an
aggregate principal amount of up to $12,000,000.00, plus any interest converted
into principal in accordance with the terms of the Subordinated Loan Agreement.

         B. RonHow has previously advanced to the Company pursuant to the
Subordinated Loan Agreement $5,000,000.00 on August 31, 2006 (the "FIRST
ADVANCE"), an additional $2,000,000.00 on January 4, 2007 (the "SECOND
ADVANCE"), and certain other advances made subsequent to the First Advance and
the Second Advance.

         C. The Company has authorized its Series 2007-A Senior Preferred Stock,
par value $0.01 per share and stated value $1,000.00 per share (the "2007-A
PREFERRED"), pursuant to a Certificate of Designation for the 2007-A Preferred
filed with the Secretary of State of the State of Oklahoma on April 26, 2007
(the "CERTIFICATE").

         D. The Company now desires to sell to RonHow, and RonHow desires to
purchase from the Company, 2,000 shares of 2007-A Preferred in exchange for the
surrender by RonHow of its rights to receive payment of, and for the
cancellation of, an amount of principal of the First Advance equal to
$2,000,000.00.

         E. Pursuant to the existing Certificates of Designation with respect to
such series of preferred stock, the existing holders of the Company's
outstanding Amended Series 2001-A Preferred Stock, Series 2002-A Preferred
Stock, Series 2003-A Preferred Stock and Series 2006-A Preferred Stock have, by
at least a majority in interest, consented to the transactions contemplated by
this Agreement.

         In consideration of the premises and the mutual promises,
representations, warranties and covenants hereinafter set forth, the Company and
RonHow agree as follows:

         1. SALE AND PURCHASE OF 2007-A PREFERRED.

                  1.1 SALE AND PURCHASE. On and subject to the terms and
         conditions of this Agreement, the Company agrees to sell, transfer and
         deliver to RonHow, and RonHow agrees to purchase from the Company,
         2,000 shares of 2007-A Preferred (the "SHARES") at the Closing (as
         hereinafter defined).

                  1.2 PURCHASE PRICE. The purchase price for the Shares shall be
         equal to $1,000.00 per Share for a total purchase price of
         $2,000,000.00 (the "PURCHASE PRICE"),

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         payable at the Closing by RonHow's surrender of its rights to receive
         payment of, and by the cancellation of, an amount of principal owed by
         the Company to RonHow out of the First Advance under the Subordinated
         Loan Agreement equal to the Purchase Price.

                  1.3 CLOSING. The closing of the transactions contemplated by
         this Agreement (the "CLOSING") shall occur at the Company's principal
         executive offices at 10:00 a.m. on the date of this Agreement.

                  1.4 DELIVERIES AT CLOSING.

                  (a) Company's Delivery at Closing. At the Closing, the Company
         shall deliver the Shares to RonHow by physical delivery of stock
         certificates representing the Shares.

                  (b) RonHow's Delivery at Closing. At the Closing, RonHow shall
         deliver the Purchase Price to the Company as provided above in Section
         1.2.

         2. REPRESENTATIONS AND WARRANTIES OF THE COMPANY. The Company
represents and warrants to RonHow that:

                  2.1 ORGANIZATION AND GOOD STANDING. The Company is a
         corporation duly organized and validly existing under the laws of the
         state of Oklahoma and is in good standing under such laws. The Company
         has all requisite corporate power and authority to own and operate its
         property and assets, and to carry on its business as presently
         conducted and as currently proposed to be conducted.

                  2.2 CORPORATE POWERS. The Company has all requisite legal and
         corporate power and authority to execute and deliver this Agreement, to
         sell and issue the Shares hereunder, to issue any additional shares of
         2007-A Preferred to be issued in satisfaction of dividends on the
         Shares (the "DIVIDEND STOCK") and to issue the Common Stock issuable
         upon conversion of the Shares and the Dividend Stock as set forth in
         the Certificate (the "UNDERLYING COMMON STOCK").

                  2.3 VALID ISSUANCE OF STOCK. The Shares, when issued, sold and
         delivered in compliance with the provisions of this Agreement, will be
         duly and validly issued, fully paid and non-assessable and issued in
         compliance with all applicable state and federal securities law. The
         Dividend Stock and the Underlying Common Stock have been or will be
         duly and validly reserved and, when issued, will be duly and validly
         issued, fully paid and non-assessable and issued in compliance with all
         applicable state and federal securities laws.

                  2.4 AUTHORIZATION. All corporate action on the part of the
         Company necessary for the authorization, execution, delivery and
         performance of this Agreement by the Company, the authorization, sale,
         issuance (or reservation of issuance) and delivery of the Shares, the
         Dividend Stock and the Underlying Common Stock with respect thereto and
         the performance of all of the Company's obligations hereunder have been
         taken prior to the date hereof. This Agreement constitutes the valid
         and legally binding obligation of the Company, enforceable in
         accordance with its terms, subject to

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         the laws of general application relating to bankruptcy, insolvency and
         the relief of debtors and the rules of law governing specific
         performance, injunctive relief or other equitable remedies.

         3. REPRESENTATIONS AND WARRANTIES OF RONHOW. RonHow represents and
warrants to the Company as follows:

                  3.1 INVESTMENT EXPERIENCE. RonHow is capable of evaluating the
         merits and risks of its investment in the Company and has the capacity
         to protect its own interests. RonHow is an "accredited investor" as
         defined in Rule 501 of Regulation D promulgated under the Securities
         Act. RonHow is able to bear the economic risk of losing its entire
         investment in the Company.

                  3.2 INVESTMENT. RonHow is acquiring the Shares for investment
         for its own account, not as a nominee or agent, and not with the view
         to, or for resale in connection with, any distribution thereof. RonHow
         understands that the Shares and the Dividend Stock and the Underlying
         Common Stock with respect thereto have not been, and will not be when
         issued, registered under the Securities Act of 1933 (the "SECURITIES
         ACT") or any state securities laws by reason of specific exemptions
         from the registration provisions of the Securities Act and such state
         laws, the availability of which depends upon, among other things, the
         bona fide nature of the investment intent and the accuracy of the
         representations as expressed herein.

                  3.3 RULE 144. RonHow is aware of the provisions of Rule 144
         promulgated under the Securities Act that permit limited resale of
         shares purchased in a private placement subject to the satisfaction of
         certain conditions, which may include, among other things, the
         existence of a public market for the shares, the availability of
         certain current public information about the Company, the resale
         occurring not less than one year after a party has purchased and paid
         for the security to be sold, the sale being effected through a
         "broker's transaction" or in transactions directly with a "market
         maker" and the number of shares being sold during any three-month
         period not exceeding specified limitations.

                  3.4 ACCESS TO INFORMATION. RonHow has had an opportunity to
         discuss the Company's management, business plan and financial condition
         with the Company's management. RonHow understands that its purchase of
         the Shares involves a high degree of risk, and there can be no
         assurance that the Company's business objectives will be obtained.

                  3.5 AUTHORIZATION. RonHow has all requisite legal power and
         authority to execute and deliver this Agreement and to carry out and
         perform its obligations under the terms of this Agreement and the
         transactions contemplated hereby. This Agreement constitutes a valid
         and legally binding obligation of RonHow, enforceable in accordance
         with its terms, subject to laws of general application relating to
         bankruptcy, insolvency and the relief of debtors and rules of law
         governing specific performance, injunctive relief or other equitable
         remedies.

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<PAGE>

                  3.6 LEGENDS. It is understood that each certificate
         representing the Shares and the Dividend Stock and the Underlying
         Common Stock with respect thereto shall bear a legend to the following
         effect:

                  THESE SECURITIES HAVE NOT BEEN REGISTERED UNDER THE SECURITIES
                  ACT OF 1933 OR ANY STATE SECURITIES LAWS. THEY MAY NOT BE
                  SOLD, OFFERED FOR SALE OR OTHERWISE TRANSFERRED IN THE ABSENCE
                  OF AN EFFECTIVE REGISTRATION STATEMENT OR THE AVAILABILITY OF
                  AN EXEMPTION THEREFROM.

         4. COVENANTS OF THE COMPANY. The Company shall at all times reserve and
keep available out of its authorized but unissued capital stock (i) such number
of shares of 2007-A Preferred as shall from time to time be sufficient to permit
payment of dividends on the Shares and Dividend Stock and (ii) such number of
shares of Underlying Common Stock as shall from time to time be sufficient to
effect the conversion of all outstanding shares of the 2007-A Preferred; and if
at any time the number of authorized but unissued shares of 2007-A Preferred or
Common Stock shall not be sufficient to effect the payment of dividends or
conversion of all then outstanding shares of the 2007-A Preferred, in addition
to such other remedies as shall be available to the holders of such 2007-A
Preferred, the Company will take such corporate action as may, in the opinion of
its counsel, be necessary to increase the authorized but unissued shares to such
number of shares as shall be sufficient for such purposes.

         5. MISCELLANEOUS.

                  5.1 GOOD FAITH; COOPERATION; FURTHER ASSURANCES. The parties
         will in good faith undertake to perform their obligations in this
         Agreement, to satisfy all conditions and to cause the transactions
         contemplated by this Agreement to be carried out promptly in accordance
         with its terms. The parties will cooperate fully with each other and
         their respective representatives in connection with any actions
         required to be taken as part of their respective obligations under this
         Agreement. Each party will at the Closing and from time to time after
         the Closing, deliver to the other such further instruments necessary or
         desirable, in the reasonable opinion of the requesting party and at the
         expense of the requesting party, to consummate or document the
         transactions contemplated by this Agreement.

                  5.2 ENTIRE AGREEMENT; SUCCESSORS AND ASSIGNS. This Agreement
         constitutes the entire agreement between the Company and RonHow
         relative to the subject matter hereof and supersedes any previous
         agreement between the Company and RonHow regarding such subject matter.
         The terms and conditions of this Agreement shall inure to the benefit
         of and be binding upon the respective executors, administrators, heirs,
         successors and assigns of the parties.

                  5.3 GOVERNING LAW. This Agreement shall be governed by and
         construed in accordance with the laws of the State of Oklahoma without
         regard to the conflicts of laws principles thereof.

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<PAGE>

                  5.4 COUNTERPARTS. This Agreement may be executed in any number
         of counterparts (including by means of facsimile or other electronic
         media) with the same effect as if all parties hereto had signed the
         same document; however, this Agreement shall not become operative until
         all parties have signed a counterpart hereof. All counterparts shall be
         construed together and shall constitute one Agreement.

                  5.5 HEADINGS. The section headings of this Agreement are for
         convenience and shall not by themselves determine the interpretation of
         this Agreement.

                  5.6 SURVIVAL OF WARRANTIES. The representations and warranties
         of the parties contained in or made pursuant to this Agreement shall
         survive for a period of one year from the date of the Closing.

                  5.7 FINDERS' FEES. The Company and RonHow shall indemnify each
         other against all liabilities incurred by one party with respect to
         claims related to investment banking or finders' fees in connection
         with the transactions contemplated by this Agreement, arising out of
         arrangements between the party asserting such claims and the
         indemnifying party, and all costs and expenses (including reasonable
         fees of counsel) of investigating and defending such claims.

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<PAGE>

         This Preferred Stock Purchase Agreement is executed and delivered by
the undersigned to be effective as of the date first above written.

"COMPANY"                            HAROLD'S STORES, INC., an Oklahoma
                                     corporation

                                     By: /s/ Jodi L. Taylor
                                         --------------------------------
                                         Jodi L. Taylor, Chief Financial Officer

"RONHOW"                             RONHOW, LLC, a Georgia limited liability
                                     company

                                     By: Ronus, Inc., a Georgia corporation,
                                         its Managing Member

                                     By: /s/ Robert L. Anderson
                                         --------------------------------
                                         Robert L. Anderson, PresidentEXHIBIT 10.9
                                                                    ------------

                                FOURTH AMENDMENT
                          TO INVESTOR RIGHTS AGREEMENT

         THIS FOURTH AMENDMENT TO INVESTOR RIGHTS AGREEMENT (this "Amendment")
is made and entered into as of the 26th day of April, 2007 (the "Effective
Date") by and among Harold's Stores, Inc., an Oklahoma corporation (the
"Company"), Inter-Him, N.V. ("Inter-Him"), W. Howard Lester ("Lester") and
RonHow, LLC, a Georgia limited liability company ("RonHow"), in order to amend
the Investor Rights Agreement dated as of February 28, 2001 by and between the
Company and Inter-Him, as amended by that certain First Amendment to Investor
Rights Agreement dated as of August 2, 2002 by and among the Company, Inter-Him,
Lester, William A. Haslam, Margaret A. Gilliam and Clark J. Hinkley, as amended
by that certain Second Amendment to Investor Rights Agreement dated as of
February 5, 2003 by and among the Company, Inter-Him and Lester, and as amended
by that certain Third Amendment to Investor Rights Agreement dated as of June 1,
2006 by and among the Company, Inter-Him and Lester (as so amended, the
"Investor Rights Agreement").

                                   WITNESSETH:

         WHEREAS, the Investor Rights Agreement provides for the attachment of
certain registration rights in the shares of Common Stock of the Company
issuable upon conversion of the Amended Series 2001-A Preferred Stock, the
Series 2002-A Preferred Stock, the Series 2003-A Preferred Stock and the Series
2006-A Preferred Stock of the Company;

         WHEREAS, the Company has granted to RonHow (i) an option to acquire up
to 3,000 shares of Series 2006-B Preferred Stock, $.01 par value per share, of
the Company (the "Series 2006-B Preferred Stock") pursuant to that certain
Option Agreement between RonHow and the Company dated August 31, 2006 and
amended April 26, 2007; and (ii) an option to acquire up to 2,000 additional
shares of Series 2006-B Preferred Stock pursuant to that certain Option
Agreement between RonHow and the Company dated January 4, 2007 and amended April
26, 2007;

         WHEREAS, the Company now desires to (i) grant to RonHow an option to
acquire up to 3,000 shares of Series 2007-B Senior Preferred Stock, $.01 par
value per share, of the Company (the "Series 2007-B Preferred Stock") pursuant
to that certain Option Agreement between RonHow and the Company dated April 26,
2007; (ii) issue to RonHow 2,000 shares of Series 2007-A Senior Preferred Stock,
$.01 par value per share, of the Company (the "Series 2007-A Preferred Stock"),
as contemplated in that certain Preferred Stock Purchase Agreement between
RonHow and the Company dated April 26, 2007, and RonHow desires to purchase such
shares as so contemplated;

         WHEREAS, the Company, Inter-Him and Lester desire to provide for the
attachment of registration rights to the shares of Common Stock of the Company
issuable upon conversion of the Series 2006-B Preferred Stock, the Series 2007-A
Preferred Stock and the Series 2007-B Preferred Stock on identical terms to
those attached to the shares of Common Stock of the

<PAGE>

Company issuable upon conversion of the Amended Series 2001-A Preferred Stock,
the Series 2002-A Preferred Stock, the Series 2003-A Preferred Stock and the
series 2006-A Preferred Stock of the Company, by amending the Investor Rights
Agreement to so provide and to include RonHow as a party to the Investor Rights
Agreement from and after the Effective Date; and

         WHEREAS, Inter-Him and Lester hold more than the minimum number of
shares of Amended Series 2001-A Preferred Stock, Series 2002-A Preferred Stock,
the Series 2003-A Preferred Stock and Series 2006-A Preferred Stock of the
Company required in order to amend the Investor Rights Agreement pursuant to
Section 2.8 thereof.

         NOW, THEREFORE, in consideration of the recitals and agreements
contained herein and the benefits to be derived from the mutual observance of
the provisions of this Fourth Amendment and the Investor Rights Agreement, the
parties agree as follows:

         1. Certain Definitions in Investor Rights Agreement. From and after the
Effective Date, the meaning of the following terms defined in the Recitals to
the Investor Rights Agreement shall be deleted, with the definitions set forth
below substituted therefor:

         (a) "Investors" shall mean Inter-Him, N.V., W. Howard Lester, William
A. Haslam, Margaret A. Gilliam, Clark J. Hinkley and RonHow, LLC ("RonHow").

         (b) "Preferred Purchase Agreement" shall mean each of:

                  (i) the 2001 Preferred Stock Purchase Agreement;

                  (ii) the 2002 Preferred Stock Purchase Agreement;

                  (iii) the 2003 Preferred Stock Purchase Agreement;

                  (iv) the 2006 Preferred Stock Purchase Agreement;

                  (v) the Preferred Stock Purchase Agreement dated April 26,
         2007 by and between RonHow and the Company for the purchase by RonHow
         of 2,000 shares of the Series 2007-A Senior Preferred Stock, $.01 par
         value, of the Company (the "2007-A Preferred Stock Purchase
         Agreement"); and

                  (vi) each agreement that may be entered into between RonHow
         and the Company that governs the purchase by RonHow of Preferred Stock
         pursuant to RonHow's full or partial exercise of its option under any
         of (A) the Option Agreement between RonHow and the Company dated August
         31, 2006 and amended as of April 26, 2007 for the purchase of Series
         2006-B Preferred Stock, $.01 par value, of the Company ("Series 2006-B
         Preferred Stock"); (B) the Option Agreement between RonHow and the
         Company dated January 4, 2007 and amended as of April 26, 2007 for the
         purchase of Series 2006-B Preferred Stock; or (C) the Option Agreement
         between RonHow and the Company dated April 26, 2007 for the purchase of
         Series 2007-B Senior Preferred Stock, $.01 par value, of the Company;
         and

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<PAGE>

         (c) "Preferred Stock" shall mean the shares of Amended Series 2001-A
Preferred Stock, $.01 par value, the shares of Series 2002-A Preferred Stock,
$.01 par value, the shares of Series 2003-A Preferred Stock, $.01 par value, the
shares of Series 2006-A Preferred Stock, $.01 par value, Series 2006-B Preferred
Stock, $.01 par value, the Series 2007-A Senior Preferred Stock, $.01 par value,
and the Series 2007-B Senior Preferred Stock, $.01 par value, of the Company.

         2. Substitution of Schedule of Investors. The Schedule of Investors
attached to the Investor Rights Agreement shall be deleted and replaced with the
Schedule of Investors attached to this Amendment as Exhibit A.

         3. Other Terms of Investor Rights Agreement. Except for the amendments
set forth herein, all other provisions of the Investor Rights Agreement shall
remain in full force and effect and shall be otherwise unaffected hereby.

         4. Counterpart Execution. This Agreement may be executed in two or more
counterparts and by facsimile, each of which shall be deemed to be an original,
but all of which together shall constitute but one and the same instrument.

                      [Signatures appear on following page]

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<PAGE>

         IN WITNESS WHEREOF, the parties hereto have executed this Fourth
Amendment as of the date above set forth.

"COMPANY"                         HAROLD'S STORES, INC.

                                  By: /s/ Jodi L. Taylor
                                      ------------------------------
                                  Name: Jodi L. Taylor
                                        ----------------------------
                                  Title: Chief Financial Officer & Secretary
                                         ------------------------------------

"INTER-HIM"                       INTER-HIM, N.V.

                                  By: /s/ Victor Hoogstraal
                                      ------------------------------
                                  Name: Victor Hoogstraal
                                        ----------------------------
                                  Title: Managing Director
                                         ---------------------------

"RONHOW"                          RONHOW, LLC

                                  By: Ronus, Inc., a Georgia corporation,

                                      Managing Member

                                  By: /s/ Robert L. Anderson
                                      ------------------------------
                                      Robert L. Anderson
                                      President

"LESTER"
                                  /s/ W. Howard Lester
                                  -------------------------------
                                  W. HOWARD LESTER

<PAGE>

                                    EXHIBIT A
                                    ---------
                              SCHEDULE OF INVESTORS

INVESTOR NAME AND ADDRESS
-------------------------

INTER-HIM, N.V.
Switzerland Representative Office
Im Langacker 16
Postfach
CH - 5401 Baden
Schweiz
Attn.: Mr. Victor Hoogstraal
Telecopy: +41 56 483 0389

W. Howard Lester
3250 Van Ness Avenue
San Francisco, California 94109
Telecopy: (415) 616-8359

William E. Haslam
5508 Lonas Road
Knoxville, Tennessee 37909
Telecopy: (865) 450-2801

Clark J. Hinkley
5919 Maple Avenue
Dallas, Texas 75235
Telecopy: (214) 902-4100

Margaret A. Gilliam
15 West 53rd Street
Suite 34A
New York, New York 10019-0001
Telecopy: (212) 765-7882

RonHow, LLC
3290 Northside Parkway, Suite 250
Atlanta, Georgia  30302
Attn:  Robert Anderson
Telecopy: (678) 553-3911

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