Document:

Exhibit 4.1

 

DIGITAL BRANDS GROUP, INC.

 

REGISTRATION RIGHTS AGREEMENT

(BLACKOAK)

 

This Registration Rights Agreement
(this “Agreement”) is made and entered into as of September 29, 2022, between Digital Brands Group, Inc., a Delaware
corporation (the “Company”), and each of the several and the holder(s) of the Company’s securities set forth
on the signature pages hereof (each such holder, an “Holder” and, collectively, the “Holders”).

 

This Agreement is made pursuant
to the Securities Purchase Agreement, dated as of September 29, 2022, between the Company and the investors named therein (as may be amended
from time to time, the “SPA”). Each of the Holders was issued Registrable Securities further to the SPA.

 

The Company and each Holder
hereby agrees as follows:

 

1.            
Definitions.

 

Capitalized terms used and
not otherwise defined herein that are defined in the SPA shall have the meanings given such terms in the SPA. As used in this Agreement,
the following terms shall have the following meanings:

 

“Advice”
shall have the meaning set forth in Section 6(b).

 

“Common
Stock” means the common stock of the Company, par value $0.0001 per share.

 

“Effectiveness
Period” shall have the meaning set forth in Section 2(a).

 

“Indemnified
Party” shall have the meaning set forth in Section 5(c).

 

“Indemnifying
Party” shall have the meaning set forth in Section 5(c).

 

“Initial
Registration Statement” means the initial Registration Statement filed pursuant to Section 2 of this Agreement.

 

“Plan of
Distribution” shall have the meaning set forth in Section 2(a).

 

“Prospectus”
means the prospectus included in a Registration Statement (including, without limitation, a prospectus that includes any information previously
omitted from a prospectus filed as part of an effective registration statement in reliance upon Rule 430A promulgated by the Commission
pursuant to the Securities Act), as amended or supplemented by any prospectus supplement, with respect to the terms of the offering of
any portion of the Registrable Securities covered by a Registration Statement, and all other amendments and supplements to the Prospectus,
including post-effective amendments, and all material incorporated by reference or deemed to be incorporated by reference in such Prospectus.

 

“Shares”
means shares of the Series A Convertible Preferred Stock of the Company.

 

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“Registrable
Securities” means, as of any date of determination, (a) the shares of Common Stock issued or issuable to the Holders
pursuant conversion of the Shares, which Shares were issued pursuant to the terms and conditions of the SPA and (b) any securities
issued or then issuable upon any share split, dividend or other distribution, recapitalization or similar event with respect to the
foregoing; provided, however, that any such Registrable Securities shall cease to be Registrable Securities (and the Company
shall not be required to maintain the effectiveness of any, or file another, Registration Statement hereunder with respect thereto)
for so long as (a) a Registration Statement with respect to the sale of such Registrable Securities is declared effective by the
Commission under the Securities Act and such Registrable Securities have been disposed of by the Holder in accordance with such
effective Registration Statement, (b) such Registrable Securities have been previously sold in accordance with Rule 144, or (c) such
securities become eligible for resale without volume or manner-of-sale restrictions and without current public information pursuant
to Rule 144 as set forth in a written opinion letter to such effect, addressed, delivered and acceptable to the Transfer Agent and
the affected Holders (assuming that such securities and any securities issuable upon exercise, conversion or exchange of which, or
as a dividend upon which, such securities were issued or are issuable, were at no time held by any Affiliate of the Company, as
reasonably determined by the Company, upon the advice of counsel to the Company.

 

“Registration
Statement” means any registration statement required to be filed hereunder pursuant to Section 2(a), and any additional registration
statements contemplated by Section 3(b) including (in each case) the Prospectus, amendments and supplements to any such registration statement
or Prospectus, including pre- and post-effective amendments, all exhibits thereto, and all material incorporated by reference or deemed
to be incorporated by reference in any such registration statement.

 

“Rule 415”
means Rule 415 promulgated by the Commission pursuant to the Securities Act, as such Rule may be amended or interpreted from time to time,
or any similar rule or regulation hereafter adopted by the Commission having substantially the same purpose and effect as such Rule.

 

“Rule 424”
means Rule 424 promulgated by the Commission pursuant to the Securities Act, as such Rule may be amended or interpreted from time to time,
or any similar rule or regulation hereafter adopted by the Commission having substantially the same purpose and effect as such Rule.

 

“Selling
Securityholder Questionnaire” shall have the meaning set forth in Section 2(a).

 

“SEC Guidance”
means (i) any publicly-available written or oral guidance of the Commission staff, or any comments, requirements or requests of the Commission
staff and (ii) the Securities Act.

 

“Transfer
Agent” means VStock Transfer, LLC.

 

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2.              Registration.

 

(a) The Company
shall uses its commercially reasonable efforts within thirty (30) days after the date hereof to prepare and file with the Commission
a Registration Statement covering the resale of 100% of the Registrable Securities for an offering to be made on a continuous basis
pursuant to Rule 415. Each Registration Statement filed hereunder shall be on Form S-1 (except if the Company is not then eligible
to register for resale the Registrable Securities on Form S-1, in which case such registration shall be on another appropriate form
in accordance herewith) and shall contain substantially the “Plan of Distribution” attached hereto
as Annex A and substantially the “Selling Securityholder” section attached hereto
as Annex B; provided, however, that no Holder shall be required to be named as an “underwriter”
without such Holder’s express prior written consent. Subject to the terms of this Agreement, the Company shall use its best
efforts to cause a Registration Statement filed under this Agreement to be declared effective under the Securities Act as promptly
as possible after the filing thereof, and shall use its best efforts to keep such Registration Statement continuously effective
under the Securities Act until the date that all Registrable Securities covered by such Registration Statement (i) have been sold,
thereunder or pursuant to Rule 144, or (ii) may be sold without volume or manner-of-sale restrictions pursuant to Rule 144 and
without the requirement for the Company to be in compliance with the current public information requirement under Rule 144, as
determined by the counsel to the Company pursuant to a written opinion letter to such effect, addressed and acceptable to the
Transfer Agent and the affected Holders (the “Effectiveness Period”). The Company shall telephonically request
effectiveness of a Registration Statement as of 5:00 p.m. (New York City time) on a Trading Day. The Company shall immediately
notify the Holders by e-mail of the effectiveness of a Registration Statement on the same Trading Day that the Company
telephonically confirms effectiveness with the Commission, which shall be the date requested for effectiveness of such Registration
Statement. The Company shall, by 9:30 a.m. (New York City time) on the Trading Day after the effective date of such Registration
Statement, file a final Prospectus with the Commission as required by Rule 424.

 

(b) Notwithstanding
the registration obligations set forth in Section 2(a), if the Commission informs the Company that all of the Registrable Securities
cannot, as a result of the application of Rule 415, be registered for resale as a secondary offering on a single registration statement,
the Company agrees to promptly inform each of the Holders thereof and use its commercially reasonable efforts to file amendments to the
Initial Registration Statement as required by the Commission, covering the maximum number of Registrable Securities permitted to be registered
by the Commission, on Form S-1 or such other form available to register for resale the Registrable Securities as a secondary offering,
subject to the provisions of Section 2(e); with respect to filing on Form S-1 or other appropriate form; provided, however,
that prior to filing such amendment, the Company shall be obligated to use diligent efforts to advocate with the Commission for the registration
of all of the Registrable Securities in accordance with the SEC Guidance, including without limitation, Compliance and Disclosure Interpretation
612.09.

 

(c) If Form S-1 is
not available for the registration of the resale of Registrable Securities hereunder, the Company shall register the resale of the Registrable
Securities on another appropriate form.

 

3.            
Registration Procedures.

 

In connection with the Company’s
registration obligations hereunder, the Company shall:

 

(a) Not less
than five (5) Trading Days prior to the filing of each Registration Statement and not less than one (1) Trading Day prior to the
filing of any related Prospectus or any amendment or supplement thereto (including any document that would be incorporated or deemed
to be incorporated therein by reference), the Company shall (i) furnish to each Holder copies of all such documents proposed to be
filed, which documents (other than those incorporated or deemed to be incorporated by reference) will be subject to the review of
such Holders, and (ii) cause its officers and directors, counsel and independent registered public accountants to respond to such
inquiries as shall be necessary, in the reasonable opinion of respective counsel to each Holder, to conduct a reasonable
investigation within the meaning of the Securities Act. The Company shall not file a Registration Statement or any such Prospectus
or any amendments or supplements thereto to which the Holders of a majority of the Registrable Securities shall reasonably object in
good faith, provided that, the Company is notified of such objection in writing no later than five (5) Trading Days after the
Holders have been so furnished copies of a Registration Statement or one (1) Trading Day after the Holders have been so furnished
copies of any related Prospectus or amendments or supplements thereto. Each Holder agrees to furnish to the Company a completed
questionnaire in the form attached to this Agreement as Annex C (a “Selling Securityholder
Questionnaire”) on a date that is not less than two (2) Trading Days prior to the Filing Date or by the end of the fourth
(4th) Trading Day following the date on which such Holder receives draft materials in accordance with this Section.

 

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(b) (i) Prepare and
file with the Commission such amendments, including post-effective amendments, to a Registration Statement and the Prospectus used in
connection therewith as may be necessary to keep a Registration Statement continuously effective as to the applicable Registrable Securities
for the Effectiveness Period and prepare and file with the Commission such additional Registration Statements in order to register for
resale under the Securities Act all of the Registrable Securities, (ii) cause the related Prospectus to be amended or supplemented
by any required Prospectus supplement (subject to the terms of this Agreement), and, as so supplemented or amended, to be filed pursuant
to Rule 424, (iii) respond as promptly as reasonably possible to any comments received from the Commission with respect to a Registration
Statement or any amendment thereto and provide as promptly as reasonably possible to the Holders true and complete copies of all correspondence
from and to the Commission relating to a Registration Statement (provided that, the Company shall excise any information contained therein
which would constitute material non-public information regarding the Company or any of its Subsidiaries), and (iv) comply in all material
respects with the applicable provisions of the Securities Act and the Exchange Act with respect to the disposition of all Registrable
Securities covered by a Registration Statement during the applicable period in accordance (subject to the terms of this Agreement) with
the intended methods of disposition by the Holders thereof set forth in such Registration Statement as so amended or in such Prospectus
as so supplemented.

 

(c) Notify the
Holders of Registrable Securities to be sold (which notice shall, pursuant to clauses (iii) through (vi) hereof, be accompanied by
an instruction to suspend the use of the Prospectus until the requisite changes have been made) as promptly as reasonably possible
(and, in the case of (i)(A) below, not less than one (1) Trading Day prior to such filing) and (if requested by any such Person)
confirm such notice in writing no later than one (1) Trading Day following the day (i)(A) when a Prospectus or any Prospectus
supplement or post-effective amendment to a Registration Statement is proposed to be filed, (B) when the Commission notifies the
Company whether there will be a “review” of such Registration Statement and whenever the Commission comments in writing
on such Registration Statement, and (C) with respect to a Registration Statement or any post-effective amendment, when the same has
become effective, (ii) of any request by the Commission or any other federal or state governmental authority for amendments or
supplements to a Registration Statement or Prospectus or for additional information, (iii) of the issuance by the Commission or
any other federal or state governmental authority of any stop order suspending the effectiveness of a Registration Statement
covering any or all of the Registrable Securities or the initiation of any Proceedings for that purpose, (iv) of the receipt by
the Company of any notification with respect to the suspension of the qualification or exemption from qualification of any of the
Registrable Securities for sale in any jurisdiction, or the initiation or threatening of any Proceeding for such purpose,
(v) of the occurrence of any event or passage of time that makes the financial statements included in a Registration Statement
ineligible for inclusion therein or any statement made in a Registration Statement or Prospectus or any document incorporated or
deemed to be incorporated therein by reference untrue in any material respect or that requires any revisions to a Registration
Statement, Prospectus or other documents so that, in the case of a Registration Statement or the Prospectus, as the case may be, it
will not contain any untrue statement of a material fact or omit to state any material fact required to be stated therein or
necessary to make the statements therein, in light of the circumstances under which they were made, not misleading, and (vi) of the
occurrence or existence of any pending corporate development with respect to the Company that the Company believes may be material
and that, in the determination of the Board of Directors of the Company in good faith, makes it not in the best interest of the
Company to allow continued availability of a Registration Statement or Prospectus; provided, however, that in no event
shall any such notice contain any information which would constitute material, non-public information regarding the Company or any
of its Subsidiaries.

 

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(d) Use its best efforts
to avoid the issuance of, or, if issued, obtain the withdrawal of (i) any order stopping or suspending the effectiveness of a Registration
Statement, or (ii) any suspension of the qualification (or exemption from qualification) of any of the Registrable Securities for sale
in any jurisdiction, at the earliest practicable moment.

 

(e) Furnish to each
Holder, without charge, at least one conformed copy of each such Registration Statement and each amendment thereto, including financial
statements and schedules, all documents incorporated or deemed to be incorporated therein by reference to the extent requested by such
Person, and all exhibits to the extent requested by such Person (including those previously furnished or incorporated by reference) promptly
after the filing of such documents with the Commission, provided that any such item which is available on the EDGAR system (or successor
thereto) need not be furnished in physical form.

 

(f) Subject to the
terms of this Agreement, the Company hereby consents to the use of such Prospectus and each amendment or supplement thereto by each of
the selling Holders in connection with the offering and sale of the Registrable Securities covered by such Prospectus and any amendment
or supplement thereto, except after the giving of any notice pursuant to Section 2(d).

 

(g) Prior to any resale
of Registrable Securities by a Holder, use its commercially reasonable efforts to register or qualify or cooperate with the selling Holders
in connection with the registration or qualification (or exemption from the Registration or qualification) of such Registrable Securities
for the resale by the Holder under the securities or Blue Sky laws of such jurisdictions within the United States as any Holder reasonably
requests in writing, to keep each registration or qualification (or exemption therefrom) effective during the Effectiveness Period and
to do any and all other acts or things reasonably necessary to enable the disposition in such jurisdictions of the Registrable Securities
covered by each Registration Statement, provided that the Company shall not be required to qualify generally to do business in any jurisdiction
where it is not then so qualified, subject the Company to any material tax in any such jurisdiction where it is not then so subject or
file a general consent to service of process in any such jurisdiction.

 

(h) If requested by
a Holder, cooperate with such Holder to facilitate the timely preparation and delivery of certificates representing Registrable Securities
to be delivered to a transferee pursuant to a Registration Statement, which certificates shall be free, to the extent permitted by the
SPA, of all restrictive legends, and to enable such Registrable Securities to be in such denominations and registered in such names as
any such Holder may request.

 

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(i) Upon the
occurrence of any event contemplated by Section 3(c), as promptly as reasonably possible under the circumstances taking into account
the Company’s good faith assessment of any adverse consequences to the Company and its shareholders of the premature
disclosure of such event, prepare a supplement or amendment, including a post-effective amendment, to a Registration Statement or a
supplement to the related Prospectus or any document incorporated or deemed to be incorporated therein by reference, and file any
other required document so that, as thereafter delivered, neither a Registration Statement nor such Prospectus will contain an
untrue statement of a material fact or omit to state a material fact required to be stated therein or necessary to make the
statements therein, in light of the circumstances under which they were made, not misleading. If the Company notifies the Holders in
accordance with clauses (iii) through (vi) of Section 3(c) above to suspend the use of any Prospectus until the requisite changes to
such Prospectus have been made, then the Holders shall suspend use of such Prospectus. The Company will use its best efforts to
ensure that the use of the Prospectus may be resumed as promptly as is practicable. The Company shall be entitled to exercise its
right under this Section 3(i) to suspend the availability of a Registration Statement and Prospectus for a period not to exceed 60
calendar days (which need not be consecutive days) in any 12-month period.

 

(j) Otherwise use
commercially reasonable efforts to comply with all applicable rules and regulations of the Commission under the Securities Act and the
Exchange Act, including, without limitation, Rule 172 under the Securities Act, file any final Prospectus, including any supplement or
amendment thereof, with the Commission pursuant to Rule 424 under the Securities Act, promptly inform the Holders in writing if, at any
time during the Effectiveness Period, the Company does not satisfy the conditions specified in Rule 172 and, as a result thereof, the
Holders are required to deliver a Prospectus in connection with any disposition of Registrable Securities and take such other actions
as may be reasonably necessary to facilitate the registration of the Registrable Securities hereunder.

 

(k) The Company may
require each selling Holder to furnish to the Company a certified statement as to the number of shares of Common Stock beneficially owned
by such Holder and, if required by the Commission, the natural persons thereof that have voting and dispositive control over the shares.

 

4.              Registration Expenses.
All fees and expenses incident to the performance of or compliance with, this Agreement by the Company shall be borne by the Company whether
or not any Registrable Securities are sold pursuant to a Registration Statement. The fees and expenses referred to in the foregoing sentence
shall include, without limitation, (i) all registration and filing fees (including, without limitation, fees and expenses of the Company’s
counsel and independent registered public accountants) (A) with respect to filings made with the Commission, (B) with respect to filings
required to be made with any Trading Market on which the shares of Common Stock are then listed for trading, and (C) in compliance with
applicable state securities or Blue Sky laws (including, without limitation, fees and disbursements of counsel for the Company in connection
with Blue Sky qualifications or exemptions of the Registrable Securities), (ii) printing expenses (including, without limitation, expenses
of printing certificates for Registrable Securities), (iii) messenger, telephone and delivery expenses, (iv) fees and disbursements of
counsel for the Company, (v) Securities Act liability insurance, if the Company so desires such insurance, and (vi) fees and expenses
of all other Persons retained by the Company in connection with the consummation of the transactions contemplated by this Agreement. In
addition, the Company shall be responsible for all of its internal expenses incurred in connection with the consummation of the transactions
contemplated by this Agreement (including, without limitation, all salaries and expenses of its officers and employees performing legal
or accounting duties), the expense of any annual audit and the fees and expenses incurred in connection with the listing of the Registrable
Securities on any securities exchange as required hereunder. In no event shall the Company be responsible for any broker or similar commissions
of any Holder or, except to the extent provided for in the Transaction Documents, any legal fees or other costs of the Holders.

 

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5.            
Indemnification.

 

(a) Indemnification
by the Company. The Company shall, notwithstanding any termination of this Agreement, indemnify and hold harmless each Holder, the
officers, directors, members, partners, agents, brokers (including brokers who offer and sell Registrable Securities as principal as a
result of a pledge or any failure to perform under a margin call), investment advisors and employees (and any other Persons with a functionally
equivalent role of a Person holding such titles, notwithstanding a lack of such title or any other title) of each of them, each Person
who controls any such Holder (within the meaning of Section 15 of the Securities Act or Section 20 of the Exchange Act) and the officers,
directors, members, shareholders, partners, agents and employees (and any other Persons with a functionally equivalent role of a Person
holding such titles, notwithstanding a lack of such title or any other title) of each such controlling Person, to the fullest extent permitted
by applicable law, from and against any and all losses, claims, damages, liabilities, costs (including, without limitation, reasonable
attorneys’ fees) and expenses (collectively, “Losses”), incurred, arising out of or relating to (1) any untrue
or alleged untrue statement of a material fact contained in a Registration Statement, any Prospectus or any form of prospectus or in any
amendment or supplement thereto or in any preliminary prospectus, or arising out of or relating to any omission or alleged omission of
a material fact required to be stated therein or necessary to make the statements therein (in the case of any Prospectus or supplement
thereto, in light of the circumstances under which they were made) not misleading or (2) any violation or alleged violation by the Company
or its directors, officers, agents and employees, of the Securities Act, the Exchange Act or any state securities law, or any rule or
regulation thereunder, in connection with the performance of its obligations under this Agreement, except to the extent, but only to the
extent, that (i) such untrue statements or omissions are based solely upon information regarding such Holder furnished in writing to the
Company by such Holder expressly for use therein, or to the extent that such information relates to such Holder or such Holder’s
proposed method of distribution of Registrable Securities and was reviewed and expressly approved in writing by such Holder expressly
for use in a Registration Statement, such Prospectus or in any amendment or supplement thereto (it being understood that the Holder has
approved Annex A hereto for this purpose) or (ii) in the case of an occurrence of an event of the type specified in Section 2(c)(iii)-(vi),
the use by such Holder of an outdated, defective or otherwise unavailable Prospectus after the Company has notified such Holder in writing
that the Prospectus is outdated, defective or otherwise unavailable for use by such Holder and prior to the receipt by such Holder of
the Advice contemplated in Section 6(b). The Company shall notify the Holders promptly of the institution, threat or assertion of any
Proceeding arising from or in connection with the transactions contemplated by this Agreement of which the Company is aware. Such indemnity
shall remain in full force and effect regardless of any investigation made by or on behalf of such indemnified person and shall survive
the transfer of any Registrable Securities by any of the Holders.

 

(b) Indemnification
by Holders. Each Holder shall, severally and not jointly, indemnify and hold harmless the Company, its directors, officers,
agents and employees, each Person who controls the Company (within the meaning of Section 15 of the Securities Act and Section 20 of
the Exchange Act), and the directors, officers, agents or employees of such controlling Persons, to the fullest extent permitted by
applicable law, from and against all Losses, as incurred, to the extent arising out of or based solely upon any untrue or alleged
untrue statement of a material fact contained in any Registration Statement, any Prospectus, or in any amendment or supplement
thereto or in any preliminary prospectus, or arising out of or relating to any omission or alleged omission of a material fact
required to be stated therein or necessary to make the statements therein (in the case of any Prospectus or supplement thereto, in
light of the circumstances under which they were made) not misleading (i) to the extent, but only to the extent, that such untrue
statement or omission is contained in any information so furnished in writing by such Holder to the Company expressly for inclusion
in such Registration Statement or such Prospectus or (ii) to the extent, but only to the extent, that such information relates to
such Holder’s information provided in the Selling Securityholder Questionnaire or the proposed method of distribution of
Registrable Securities and was reviewed and expressly approved in writing by such Holder expressly for use in a Registration
Statement (it being understood that the Holder has approved Annex A hereto for this purpose), such Prospectus or in any amendment or
supplement thereto. In no event shall the liability of a selling Holder be greater in amount than the dollar amount of the proceeds
(net of all expenses paid by such Holder in connection with any claim relating to this Section 5 and the amount of any damages such
Holder has otherwise been required to pay by reason of such untrue statement or omission) received by such Holder upon the sale of
the Registrable Securities included in the Registration Statement giving rise to such indemnification obligation.

 

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(c) Conduct of
Indemnification Proceedings. If any Proceeding shall be brought or asserted against any Person entitled to indemnity hereunder (an
 “Indemnified Party”), such Indemnified Party shall promptly notify the Person from whom indemnity is sought (the “Indemnifying
Party”) in writing, and the Indemnifying Party shall have the right to assume the defense thereof, including the employment
of counsel reasonably satisfactory to the Indemnified Party and the payment of all fees and expenses incurred in connection with defense
thereof, provided that the failure of any Indemnified Party to give such notice shall not relieve the Indemnifying Party of its obligations
or liabilities pursuant to this Agreement, except (and only) to the extent that it shall be finally determined by a court of competent
jurisdiction (which determination is not subject to appeal or further review) that such failure shall have materially and adversely prejudiced
the Indemnifying Party.

 

An Indemnified Party
shall have the right to employ separate counsel in any such Proceeding and to participate in the defense thereof, but the fees and expenses
of such counsel shall be at the expense of such Indemnified Party or Parties unless: (1) the Indemnifying Party has agreed in writing
to pay such fees and expenses, (2) the Indemnifying Party shall have failed promptly to assume the defense of such Proceeding and to employ
counsel reasonably satisfactory to such Indemnified Party in any such Proceeding, or (3) the named parties to any such Proceeding (including
any impleaded parties) include both such Indemnified Party and the Indemnifying Party, and counsel to the Indemnified Party shall reasonably
believe that a material conflict of interest is likely to exist if the same counsel were to represent such Indemnified Party and the Indemnifying
Party (in which case, if such Indemnified Party notifies the Indemnifying Party in writing that it elects to employ separate counsel at
the expense of the Indemnifying Party, the Indemnifying Party shall not have the right to assume the defense thereof and the reasonable
fees and expenses of no more than one separate counsel shall be at the expense of the Indemnifying Party). The Indemnifying Party shall
not be liable for any settlement of any such Proceeding effected without its written consent, which consent shall not be unreasonably
withheld or delayed. No Indemnifying Party shall, without the prior written consent of the Indemnified Party, effect any settlement of
any pending Proceeding in respect of which any Indemnified Party is a party, unless such settlement includes an unconditional release
of such Indemnified Party from all liability on claims that are the subject matter of such Proceeding.

 

Subject to the
terms of this Agreement, all reasonable fees and expenses of the Indemnified Party (including reasonable fees and expenses to the
extent incurred in connection with investigating or preparing to defend such Proceeding in a manner not inconsistent with this
Section) shall be paid to the Indemnified Party, as incurred, within ten (10) Trading Days of written notice thereof to the
Indemnifying Party, provided that the Indemnified Party shall promptly reimburse the Indemnifying Party for that portion of such
fees and expenses applicable to such actions for which such Indemnified Party is finally determined by a court of competent
jurisdiction (which determination is not subject to appeal or further review) not to be entitled to indemnification hereunder.

 

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(d) Contribution.
If the indemnification under Section 5(a) or 5(b) is unavailable to an Indemnified Party or insufficient to hold an Indemnified Party
harmless for any Losses, then each Indemnifying Party shall contribute to the amount paid or payable by such Indemnified Party, in such
proportion as is appropriate to reflect the relative fault of the Indemnifying Party and Indemnified Party in connection with the actions,
statements or omissions that resulted in such Losses as well as any other relevant equitable considerations. The relative fault of such
Indemnifying Party and Indemnified Party shall be determined by reference to, among other things, whether any action in question, including
any untrue or alleged untrue statement of a material fact or omission or alleged omission of a material fact, has been taken or made by,
or relates to information supplied by, such Indemnifying Party or Indemnified Party, and the parties’ relative intent, knowledge,
access to information and opportunity to correct or prevent such action, statement or omission. The amount paid or payable by a party
as a result of any Losses shall be deemed to include, subject to the limitations set forth in this Agreement, any reasonable attorneys’
or other fees or expenses incurred by such party in connection with any Proceeding to the extent such party would have been indemnified
for such fees or expenses if the indemnification provided for in this Section was available to such party in accordance with its terms.

 

The parties hereto
agree that it would not be just and equitable if contribution pursuant to this Section 5(d) were determined by pro rata allocation or
by any other method of allocation that does not take into account the equitable considerations referred to in the immediately preceding
paragraph. In no event shall the contribution obligation of a Holder of Registrable Securities be greater in amount than the dollar amount
of the proceeds (net of all expenses paid by such Holder in connection with any claim relating to this Section 5 and the amount of any
damages such Holder has otherwise been required to pay by reason of such untrue or alleged untrue statement or omission or alleged omission)
received by it upon the sale of the Registrable Securities giving rise to such contribution obligation.

 

The indemnity and
contribution agreements contained in this Section are in addition to any liability that the Indemnifying Parties may have to the Indemnified
Parties.

 

6.              
Miscellaneous.

 

(a) Remedies.
In the event of a breach by the Company or by a Holder of any of their respective obligations under this Agreement, each Holder or the
Company, as the case may be, in addition to being entitled to exercise all rights granted by law and under this Agreement, including recovery
of damages, shall be entitled to specific performance of its rights under this Agreement. Each of the Company and each Holder agrees that
monetary damages would not provide adequate compensation for any losses incurred by reason of a breach by it of any of the provisions
of this Agreement and hereby further agrees that, in the event of any action for specific performance in respect of such breach, it shall
not assert or shall waive the defense that a remedy at law would be adequate.

 

(b) Discontinued
Disposition. By its acquisition of Registrable Securities, each Holder agrees that, upon receipt of a notice from the Company of
the occurrence of any event of the kind described in Section 3(c)(iii) through (vi), such Holder will forthwith discontinue
disposition of such Registrable Securities under a Registration Statement until it is advised in writing (the
 “Advice”) by the Company that the use of the applicable Prospectus (as it may have been supplemented or amended)
may be resumed. The Company will use its best efforts to ensure that the use of the Prospectus may be resumed as promptly as is
practicable.

 

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(c) Amendments
and Waivers. The provisions of this Agreement, including the provisions of this sentence, may not be amended, modified or supplemented,
and waivers or consents to departures from the provisions hereof may not be given, unless the same shall be in writing and signed by the
Company and the Holders of 50.1% or more of the then outstanding Registrable Securities (for purposes of clarification, this includes
any Registrable Securities issuable upon exercise or conversion of any security), provided that, if any amendment, modification or waiver
disproportionately and adversely impacts a Holder (or group of Holders), the consent of such disproportionately impacted Holder (or group
of Holders) shall be required. If a Registration Statement does not register all of the Registrable Securities pursuant to a waiver or
amendment done in compliance with the previous sentence, then the number of Registrable Securities to be registered for each Holder shall
be reduced pro rata among all Holders and each Holder shall have the right to designate which of its Registrable Securities shall be omitted
from such Registration Statement. Notwithstanding the foregoing, a waiver or consent to depart from the provisions hereof with respect
to a matter that relates exclusively to the rights of a Holder or some Holders and that does not directly or indirectly affect the rights
of other Holders may be given only by such Holder or Holders of all of the Registrable Securities to which such waiver or consent relates; provided, however,
that the provisions of this sentence may not be amended, modified, or supplemented except in accordance with the provisions of the first
sentence of this Section 5(d). No consideration shall be offered or paid to any Person to amend or consent to a waiver or modification
of any provision of this Agreement unless the same consideration also is offered to all of the parties to this Agreement.

 

(d) Notices.
Any and all notices or other communications or deliveries required or permitted to be provided hereunder shall be delivered as set forth
in the SPA.

 

(e) Successors
and Assigns. This Agreement shall inure to the benefit of and be binding upon the successors and permitted assigns of each of the
parties and shall inure to the benefit of each Holder. The Company may not assign (except by merger) its rights or obligations hereunder
without the prior written consent of all of the Holders of the then outstanding Registrable Securities.

 

(f) No Inconsistent
Agreements. Neither the Company nor any of its Subsidiaries has entered, as of the date hereof, nor shall the Company or any of its
Subsidiaries, on or after the date of this Agreement, enter into any agreement with respect to its securities, that would have the effect
of impairing the rights granted to the Holders in this Agreement or otherwise conflicts with the provisions hereof.

 

(g) Execution and
Counterparts. This Agreement may be executed in two or more counterparts, all of which when taken together shall be considered one
and the same agreement and shall become effective when counterparts have been signed by each party and delivered to the other party, it
being understood that both parties need not sign the same counterpart. In the event that any signature is delivered by facsimile transmission
or by e-mail delivery of a “.pdf” format data file, such signature shall create a valid and binding obligation of the party
executing (or on whose behalf such signature is executed) with the same force and effect as if such facsimile or “.pdf” signature
page were an original thereof.

 

    10

     

    

 

(h) Governing Law.
All questions concerning the construction, validity, enforcement and interpretation of this Agreement shall be determined in accordance
with the provisions of the SPA.

 

(i) Cumulative
Remedies. The remedies provided herein are cumulative and not exclusive of any other remedies provided by law.

 

(j) Severability.
If any term, provision, covenant or restriction of this Agreement is held by a court of competent jurisdiction to be invalid, illegal,
void or unenforceable, the remainder of the terms, provisions, covenants and restrictions set forth herein shall remain in full force
and effect and shall in no way be affected, impaired or invalidated, and the parties hereto shall use their commercially reasonable efforts
to find and employ an alternative means to achieve the same or substantially the same result as that contemplated by such term, provision,
covenant or restriction. It is hereby stipulated and declared to be the intention of the parties that they would have executed the remaining
terms, provisions, covenants and restrictions without including any of such that may be hereafter declared invalid, illegal, void or unenforceable.

 

(k) Headings.
The headings in this Agreement are for convenience only, do not constitute a part of the Agreement and shall not be deemed to limit or
affect any of the provisions hereof.

 

(l) Independent
Nature of Holders’ Obligations and Rights. The obligations of each Holder hereunder are several and not joint with the obligations
of any other Holder hereunder, and no Holder shall be responsible in any way for the performance of the obligations of any other Holder
hereunder. Nothing contained herein or in any other agreement or document delivered at any closing, and no action taken by any Holder
pursuant hereto or thereto, shall be deemed to constitute the Holders as a partnership, an association, a joint venture or any other kind
of group or entity, or create a presumption that the Holders are in any way acting in concert or as a group or entity with respect to
such obligations or the transactions contemplated by this Agreement or any other matters, and the Company acknowledges that the Holders
are not acting in concert or as a group, and the Company shall not assert any such claim, with respect to such obligations or transactions.
Each Holder shall be entitled to protect and enforce its rights, including without limitation the rights arising out of this Agreement,
and it shall not be necessary for any other Holder to be joined as an additional party in any proceeding for such purpose. The use of
a single agreement with respect to the obligations of the Company contained was solely in the control of the Company, not the action or
decision of any Holder, and was done solely for the convenience of the Company and not because it was required or requested to do so by
any Holder. It is expressly understood and agreed that each provision contained in this Agreement is between the Company and a Holder,
solely, and not between the Company and the Holders collectively and not between and among Holders.

 

********************

 

(Signature Pages Follow)

 

    11

     

    

 

IN WITNESS WHEREOF,
the parties have executed this Registration Rights Agreement as of the date first written above.

 

	 	DIGITALBRANDS GROUP, INC.
	 	
     
	 
	 	By:	/s/ John
Hilburn Davis IV          
	 	Name:	John Hilburn Davis IV
	 	Title:	Chief Executive Officer

 

[SIGNATURE PAGE OF HOLDERS FOLLOWS]

 

    12

     

    

 

[SIGNATURE
PAGE OF HOLDERS]

 

Name of Holder: bocm4-DSTLD-Senior Debt, LLC

 

Signature of Authorized Signatory of Holder:
__/s/ Kurt Hanson__________

 

Name of Authorized Signatory:       Kurt Hanson_______________________

 

Title of Authorized Signatory: ___Manager /
Partner_______________________

 

    13

     

    

 

Annex A

Plan of Distribution

 

Each Selling Securityholder
(the “Selling Securityholder”) of the securities and any of their pledgees, assignees and successors-in-interest may,
from time to time, sell any or all of their securities covered hereby on the principal Trading Market or any other stock exchange, market
or trading facility on which the securities are traded or in private transactions. These sales may be at fixed or negotiated prices. A
Selling Securityholder may use any one or more of the following methods when selling securities:

 

	 	●	ordinary brokerage transactions and transactions in which the broker-dealer solicits purchasers;
	 	 	 
	 	●	block trades in which the broker-dealer will attempt to sell the securities as agent but may position and resell a portion of the block as principal to facilitate the transaction;
	 	 	 
	 	●	purchases by a broker-dealer as principal and resale by the broker-dealer for its account;
	 	 	 
	 	●	an exchange distribution in accordance with the rules of the applicable exchange;
	 	 	 
	 	●	privately negotiated transactions;
	 	 	 
	 	●	settlement of short sales;
	 	 	 
	 	●	in transactions through broker-dealers that agree with the Selling Securityholders to sell a specified number of such securities at a stipulated price per security;
	 	 	 
	 	●	through the writing or settlement of options or other hedging transactions, whether through an options exchange or otherwise;
	 	 	 
	 	●	a combination of any such methods of sale; or
	 	 	 
	 	●	any other method permitted pursuant to applicable law.

 

The Selling Securityholders
may also sell securities under Rule 144 or any other exemption from registration under the Securities Act of 1933, as amended (the “Securities
Act”), if available, rather than under this prospectus.

 

Broker-dealers engaged by
the Selling Securityholders may arrange for other brokers-dealers to participate in sales. Broker-dealers may receive commissions or discounts
from the Selling Securityholders (or, if any broker-dealer acts as agent for the purchaser of securities, from the purchaser) in amounts
to be negotiated, but, except as set forth in a supplement to this Prospectus, in the case of an agency transaction not in excess of a
customary brokerage commission in compliance with FINRA Rule 2121; and in the case of a principal transaction a markup or markdown in
compliance with FINRA Rule 2121.

 

In connection with the
sale of the securities or interests therein, the Selling Securityholders may enter into hedging transactions with broker-dealers or
other financial institutions, which may in turn engage in short sales of the securities in the course of hedging the positions they
assume. The Selling Securityholders may also sell securities short and deliver these securities to close out their short positions,
or loan or pledge the securities to broker-dealers that in turn may sell these securities. The Selling Securityholders may also
enter into option or other transactions with broker-dealers or other financial institutions or create one or more derivative
securities which require the delivery to such broker-dealer or other financial institution of securities offered by this prospectus,
which securities such broker-dealer or other financial institution may resell pursuant to this prospectus (as supplemented or
amended to reflect such transaction).

 

    14

    

    

 

The Selling Securityholders
and any broker-dealers or agents that are involved in selling the securities may be deemed to be “underwriters” within the
meaning of the Securities Act in connection with such sales. In such event, any commissions received by such broker-dealers or agents
and any profit on the resale of the securities purchased by them may be deemed to be underwriting commissions or discounts under the Securities
Act. Each Selling Securityholders has informed the Company that it does not have any written or oral agreement or understanding, directly
or indirectly, with any person to distribute the securities.

 

The Company is required to
pay certain fees and expenses incurred by the Company incident to the registration of the securities. The Company has agreed to indemnify
the Selling Securityholders against certain losses, claims, damages and liabilities, including liabilities under the Securities Act.

 

We agreed to keep this prospectus
effective until the earlier of (i) the date on which the securities may be resold by the Selling Securityholders without registration
and without regard to any volume or manner-of-sale limitations by reason of Rule 144, without the requirement for the Company to be in
compliance with the current public information under Rule 144 under the Securities Act or any other rule of similar effect or (ii) all
of the securities have been sold pursuant to this prospectus or Rule 144 under the Securities Act or any other rule of similar effect.
The resale securities will be sold only through registered or licensed brokers or dealers if required under applicable state securities
laws. In addition, in certain states, the resale securities covered hereby may not be sold unless they have been registered or qualified
for sale in the applicable state or an exemption from the registration or qualification requirement is available and is complied with.

 

Under applicable rules and
regulations under the Exchange Act, any person engaged in the distribution of the resale securities may not simultaneously engage in market
making activities with respect to the shares of Common Stock for the applicable restricted period, as defined in Regulation M, prior to
the commencement of the distribution. In addition, the Selling Securityholders will be subject to applicable provisions of the Exchange
Act and the rules and regulations thereunder, including Regulation M, which may limit the timing of purchases and sales of the shares
of Common Stock by the Selling Securityholders or any other person. We will make copies of this prospectus available to the Selling Securityholders
and have informed them of the need to deliver a copy of this prospectus to each purchaser at or prior to the time of the sale (including
by compliance with Rule 172 under the Securities Act).

 

    15

    

    

 

Annex B

 

SELLING SECURITYHOLDERS

 

The shares of Common Stock
being offered by the Selling Securityholders are those issuable to the Selling Securityholders upon exercise of the Convertible Notes.
For additional information regarding the issuances of those shares of Common Stock underlying the Convertible Notes, see “Private
Placement of Convertible Notes” above. We are registering the shares of Common Stock underlying the Convertible Notes in order to
permit the Selling Securityholders to offer the shares for resale from time to time. Except for the ownership of the shares of Common
Stock, the Selling Securityholders have not had any material relationship with us within the past three years, except as contemplated
by the SPA.

 

The table below lists the
Selling Securityholders and other information regarding the beneficial ownership of the shares of Common Stock by each of the Selling
Securityholders. The second column lists the number of shares of Common Stock beneficially owned by each Selling Securityholder, based
on its ownership of the shares of Common Stock, as of ________, 2022.

 

The third column lists the
shares of Common Stock being offered by this prospectus by the Selling Securityholders.

 

In accordance with the terms
of a registration rights agreement with the Selling Securityholders, this prospectus generally covers the resale 200% of the sum of the
number of shares of Common Stock issuable to the Selling Securityholders upon conversion of the Convertible Notes, as described in “Private
Placement of Convertible Notes” above. The fourth column assumes the sale of all of the shares offered by the Selling Securityholders
pursuant to this prospectus.

 

The Selling Securityholders
may sell all, some or none of their shares in this offering. See “Plan of Distribution.”

 

	Name of Selling Securityholder	 	Number of shares 

of Common Stock 

Owned Prior to 

Offering	 	Maximum Number 

of shares of 

Common Stock to 

be Sold Pursuant to 

this Prospectus	 	Number of shares 

of Common Stock 

Owned After 

Offering
	 	 	 	 	 	 	 
	 	 	 	 	 	 	 
	 	 	 	 	 	 	 

 

    16

    

    

 

Annex C

 

DIGITAL
BRANDS GROUP, INC.

 

Selling Securityholder Notice and Questionnaire

 

The undersigned beneficial
owner of shares of Common Stock (the “Registrable Securities”) of Digital Brands Group, Inc., a Delaware corporation
(the “Company”), understands that the Company has filed or intends to file with the Securities and Exchange Commission
(the “Commission”) a registration statement (the “Registration Statement”) for the registration
and resale under Rule 415 of the Securities Act of 1933, as amended (the “Securities Act”), of the Registrable
Securities, in accordance with the terms of the Registration Rights Agreement (the “Registration Rights Agreement”)
to which this document is annexed. A copy of the Registration Rights Agreement is available from the Company upon request at the address
set forth below. All capitalized terms not otherwise defined herein shall have the meanings ascribed thereto in the Registration Rights
Agreement.

 

Certain legal consequences
arise from being named as a Selling Securityholder in the Registration Statement and the related prospectus. Accordingly, holders and
beneficial owners of Registrable Securities are advised to consult their own securities law counsel regarding the consequences of being
named or not being named as a Selling Securityholder in the Registration Statement and the related prospectus.

 

NOTICE

 

The undersigned beneficial owner (the “Selling
Securityholder”) of Registrable Securities hereby elects to include the Registrable Securities owned by it in the Registration
Statement.

 

The undersigned hereby provides the following information
to the Company and represents and warrants that such information is accurate:

 

    17

    

    

 

QUESTIONNAIRE

 

	1.	Name.

 

	 	(a)	Full Legal Name of Selling Securityholder
	 	 	 
	 	 	 

 

	 	(b)	Full Legal Name of Registered Holder (if not the same as (a) above) through which Registrable Securities are held:
	 	 	 
	 	 	 

 

	 	(c)	Full Legal Name of Natural Control Person (which means a natural person who directly or indirectly alone or with others has power to vote or dispose of the securities covered by this Questionnaire):
	 	 	 
	 	 	 

 

		2.	Address for Notices to Selling Securityholder:

 

	 
	 
	 

	Telephone:	 

	Fax:	 

	Contact Person:	 

 

		3.	Broker-Dealer Status:

 

	 	(a)	Are you a broker-dealer?
	 	 	 
	Yes    ̈              No    ̈

 

	 	(b)	If “yes” to Section 3(a), did you receive your Registrable Securities as compensation for investment banking services to the Company?
	 	 	 
	Yes    ̈              No    ̈

 

	 	Note:	If “no” to Section 3(b), the Commission’s staff has indicated that you should be identified as an underwriter in the Registration Statement.
	 

 

	 	(c)	Are you an affiliate of a broker-dealer?

 

	Yes   ☐              No   ☐

 

    18

    

    

 

	 	(d)	If you are an affiliate of a broker-dealer, do you certify that you purchased the Registrable Securities in the ordinary course of business, and at the time of the purchase of the Registrable Securities to be resold, you had no agreements or understandings, directly or indirectly, with any person to distribute the Registrable Securities?
	 	 	 
	Yes     ̈             No    ̈

 

	 	Note:	If “no” to Section 3(d), the Commission’s staff has indicated that you should be identified as an underwriter in the Registration Statement.

 

		4.	Beneficial Ownership of Securities of the Company Owned by the Selling Securityholder.

 

Except as set forth below in this
Item 4, the undersigned is not the beneficial or registered owner of any securities of the Company other than the securities issuable
pursuant to the SPA.

 

	 	(a)	Type and Amount of other securities beneficially owned by the Selling Securityholder:
	 	 	 
	 	 	 
	 	 	 

 

		5.	Relationships with the Company:

 

Except as set forth below, neither
the undersigned nor any of its affiliates, officers, directors or principal equity holders (owners of 5% of more of the equity securities
of the undersigned) has held any position or office or has had any other material relationship with the Company (or its predecessors or
affiliates) during the past three years.

 

State any exceptions here:

 

	 	 
	 	 

 

The undersigned agrees to promptly notify the
Company of any material inaccuracies or changes in the information provided herein that may occur subsequent to the date hereof at any
time while the Registration Statement remains effective; provided, that the undersigned shall not be required to notify the Company of
any changes to the number of securities held or owned by the undersigned or its affiliates.

 

By signing below, the undersigned consents to
the disclosure of the information contained herein in its answers to Items 1 through 5 and the inclusion of such information in the Registration
Statement and the related prospectus and any amendments or supplements thereto. The undersigned understands that such information will
be relied upon by the Company in connection with the preparation or amendment of the Registration Statement and the related prospectus
and any amendments or supplements thereto.

 

    19

    

    

 

IN WITNESS WHEREOF the undersigned,
by authority duly given, has caused this Notice and Questionnaire to be executed and delivered either in person or by its duly authorized
agent.

 

	Date:	 	 	Beneficial Owner:	 

 

	 	 	By:	 
	 	 	Name:	 
	 	 	Title:	 

 

PLEASE FAX A COPY (OR EMAIL A .PDF COPY) OF
THE COMPLETED AND EXECUTED NOTICE AND QUESTIONNAIRE TO:

 

    20Exhibit 10.1

 

SECURITIES PURCHASE
AGREEMENT

 

This SECURITIES PURCHASE
AGREEMENT (the “Agreement”), dated as of September 29, 2022, is by and among Digital Brands Group, Inc., a Delaware
corporation (the “Company”), and each of the investors listed on Schedule I (individually, a “Investor”
and collectively, the “Investors”).

 

RECITALS

 

A.               
The Company and each Investor is executing and delivering this Agreement in reliance upon the exemption from securities registration
afforded by Section 4(a)(2) of the Securities Act of 1933, as amended (the “1933 Act”), and Rule 506(b) of Regulation
D (“Regulation D”) as promulgated by the United States Securities and Exchange Commission (the “SEC”)
under the 1933 Act.

 

B.                
The Company has authorized a new series of convertible preferred stock of the Company designated as Series A Convertible Preferred
Stock, par value $0.0001 per share, the terms of which are set forth in the certificate of designation for such series of Preferred Stock
(the “Certificate of Designations”) in the form attached hereto as Exhibit A (together with any convertible
preferred shares issued in replacement thereof in accordance with the terms thereof, the “Series A Preferred Stock”),
which Series A Preferred Stock shall be convertible into shares of Common Stock (as defined below) (such shares of Common Stock issuable
pursuant to the terms of the Certificate of Designations, including, without limitation, upon conversion or otherwise, collectively, the
 “Conversion Shares”), in accordance with the terms of the Certificate of Designations.

 

C.                
Each Investor wishes to purchase, and the Company wishes to sell, upon the terms and conditions stated in this Agreement, (i) the
aggregate number of shares of Series A Preferred Stock (the “Shares”) set forth opposite such Investor’s name
on Schedule I.

 

D.               
At the Closing, the parties hereto shall execute and deliver a Registration Rights Agreement, in the form attached hereto as Exhibit
B (the “Registration Rights Agreement”), pursuant to which the Company has agreed to provide certain registration
rights with respect to the Registrable Securities (as defined in the Registration Rights Agreement), under the 1933 Act and the rules
and regulations promulgated thereunder, and applicable state securities laws.

 

E.                
The Shares and the Conversion Shares are collectively referred to herein as the “Securities.”

 

NOW THEREFORE, THE PARTIES
AGREE AS FOLLOWS:

 

1.0             
Basic Terms of Purchase and Sale.

 

1.1             
Purchase and Sale of Series A Preferred Stock.

 

(a)              
Subject to the terms and conditions of this Agreement, each of the Investors agree to purchase from the Company, and the Company
agrees to sell and issue to each of the Investors, at the Closing that number of Shares as is set forth opposite such Investor’s
name on Schedule I at $1,000 per Share, with the aggregate amount to be paid by each Investor being as stated on Schedule I
opposite such Investor’s name, in consideration for the cancellation of promissory notes issued by the Company to the Investors,
in the principal amount set forth opposite such Investor’s name on Schedule I, pursuant to that certain Loan
Agreement with bocm3-DSTLD-Senior Debt, LLC (the “Black Oak Capital”) dated March 10, 2017, and as amended on February
28, 2019 (together the “Loan Agreements”). To facilitate the issuance of shares in accordance with the provisions
of this Agreement, the Company may round the number of Shares allocated to any Investor up to the nearest whole number. The Company’s
agreements with each of the Investors are separate agreements, and the sale of the Shares to each of the Investors are separate sales.

 

     

     

    

 

Investors
agree that in no event will Investors in the aggregate convert in any calendar month more than the greater of (i) $500,000 of Shares (measure
by the number of shares of common stock underlying the Shares to be converted multiplied by the then conversion price per Share) or (ii)
Shares which underlying shares of common stock comprises more than 10% of the aggregate trading volume of the Company’s common stock
as reported by Nasdaq.

 

(b)              
As soon as practicable after the date hereof, the Company shall deliver to each Investor purchasing Shares therein a certificate
representing that number of the Shares set forth on Schedule I opposite the name of such Investor against delivery to the
Company by the Investors of evidence of the cancellation of all amounts owing under the Loan Agreements.

 

2.0             
Representations and Warranties.

 

2.1             
Representations and Warranties of the Company. The Company hereby represents and warrants to the Investors as follows:

 

(a)              
Incorporation. The Company is a corporation duly organized, validly existing and in good standing under the laws of the
State of Delaware and has all requisite corporate power and authority to carry on its business as now conducted and as proposed to be
conducted.

 

(b)              
Authorization. All corporate action on the part of the Company, its officers, directors and shareholders necessary for the
authorization, execution, delivery and performance of this Agreement, the Registration Rights Agreement, and the consummation of the transactions
contemplated herein and therein, and for the authorization, issuance and delivery of the Shares, has been or shall be taken prior to the
Closing, and this Agreement and the Registration Rights Agreement, when executed and delivered, shall constitute the legal, valid and
binding obligation of the Company, enforceable against the Company in accordance with their respective terms, except as limited by applicable
bankruptcy, insolvency, reorganization, moratorium, or other laws of general application relating to or affecting the enforcement of creditors’
rights. The Company has all requisite legal and corporate power to enter into this Agreement and the Registration Rights Agreement, to
sell the Shares hereunder, and to carry out and perform its obligations hereunder and thereunder.

 

     

     

    

 

(c)              
 Valid Issuance of the Shares. The Shares to be purchased by the Investors hereunder (and the common stock issuable upon
conversion of the Shares) will, upon issuance pursuant to the terms hereof (or upon conversion of the Shares), be duly and validly issued,
fully paid and nonassessable and will be free from any liens or encumbrances created by the Company (except as provided in this Agreement
with respect to federal and applicable state securities laws). Based in part upon the representations of the Investors in Section 3
of this Agreement, the Shares (and the common stock issuable upon conversion of the Shares), when issued and delivered pursuant to this
Agreement, will be issued in compliance with federal and all applicable state securities laws. Subject in part to the truth and accuracy
of each Investor’s representations set forth in Section 3 of this Agreement, the offer, sale and issuance of the Shares as contemplated
by this Agreement are exempt from the registration requirements of the Securities Act of 1933, as amended, and neither the Company nor
any authorized agent acting on its behalf has taken or will take any action hereafter that would cause the loss of such exemption.

 

(d)              
Governmental Consents. All consents, approvals, orders, authorizations, registrations, qualifications, designations, declarations
or filings with any federal or state governmental agency or authority required on the part of the Company in connection with the execution,
delivery or performance of this Agreement and the consummation of the transactions contemplated herein shall have been obtained prior
to, and be effective as of, the Closing.

 

(e)              
Compliance with Other Instruments. The execution, delivery and performance of and compliance with this Agreement and the
Registration Rights Agreement, and the sale of the Shares pursuant to the terms hereof and thereof, will not result in any violation or
be in conflict with or constitute a default under any such provision, or result in the creation of any mortgage, pledge, lien, encumbrance
or charge upon any of the properties or assets of the Company pursuant to any such provision.

 

3.0             
Representations and Warranties of the Investor.

 

Each Investor hereby severally
represents and warrants to the Company as follows:

 

3.1             
Authorization. When executed and delivered by such Investor, this Agreement will constitute the valid and legally binding
obligation of such Investor, enforceable in accordance with its terms, except as limited by applicable bankruptcy, insolvency, reorganization,
moratorium, or other laws of general application relating to or affecting the enforcement of creditors’ rights.

 

3.2             
Purchase Entirely for Own Account. Such Investor is acquiring the Shares hereunder for its own account for investment purposes
only and not with a view to, or for resale in connection with, any “distribution” of all or any portion thereof within the
meaning of the 1933 Act.

 

3.3             
Disclosure of Information. Such Investor believes that it has received all the information it considers necessary or appropriate
for deciding whether to purchase Shares hereunder. Such Investor further represents that it has had an opportunity to ask questions and
receive answers from the Company regarding its business and prospects. The foregoing, however, does not limit or modify the representations and
warranties of the Company in Section 2 of this Agreement or the right of such Investor to rely thereon.

 

     

     

    

  

3.4             
Experience. Such Investor is experienced in evaluating and investing in companies such as the Company. Such Investor understands
that the investment to be made in connection with the acquisition of Shares hereunder is speculative and involves significant risk. Such
Investor has no need for liquidity in this investment, has the ability to bear the economic risk of this investment, and can afford a
complete loss of the purchase price. Such Investor is an “accredited investor” as that term is defined within Regulation D
promulgated under the 1933 Act.

 

3.5             
Restricted Securities. Such Investor understands that the Shares being purchased hereunder (and the common stock issuable
upon conversion thereof) are characterized as “restricted securities” under the federal securities laws inasmuch as they are
being acquired from the Company in a transaction not involving a public offering and that under such laws and applicable regulations such
securities may be resold without registration under the 1933 Act only in certain limited circumstances. In this connection, such Investor
represents that it is familiar with Rule 144 promulgated by the SEC, as presently in effect, and understands the resale limitations
imposed thereby and by the 1933 Act.

 

3.6             
Further Limitations on Disposition. Without in any way limiting the representations set forth above, such Investor further
agrees not to make any disposition of all or any portion of the Shares being purchased hereunder (or of the common stock issuable upon
conversion of the Shares) except in compliance with applicable state securities laws and unless:

 

(a)              
there is then in effect a registration statement under the 1933 Act covering such proposed disposition and such disposition is
made in accordance with such registration statement;

 

(b)              
such disposition involves: (i) a transfer not involving a change in beneficial ownership; (ii) a transfer in compliance
with Rule 144, so long as the Company is furnished with satisfactory evidence of compliance with such Rule; (iii) transfers
by any holder who is an individual to a trust for the benefit of such holder or his family; or (iv) transfers by gift, will or intestate
succession to the spouse, lineal descendants or ancestors of any holder or spouse of a holder; or

 

(c)              
such Investor shall have notified the Company of the proposed disposition and shall have furnished the Company with a detailed
statement of the circumstances surrounding the proposed disposition, and, if requested by the Company, such Investor shall have furnished
the Company with an opinion of counsel, which opinion and counsel shall be reasonably satisfactory to the Company, that such disposition
will not require registration under the 1933 Act and will be in compliance with applicable state securities laws.

 

3.7 Legends. Each
Investor understands that the Securities have been issued (or will be issued in the case of the Conversion Shares) pursuant to an exemption
from registration or qualification under the 1933 Act and applicable state securities laws, and except as set forth below, the Securities
shall bear any legend as required by the “blue sky” laws of any state and a restrictive legend in substantially the following
form (and a stop-transfer order may be placed against transfer of such stock certificates):

 

     

     

    

 

NEITHER THE ISSUANCE AND SALE OF THE SECURITIES
REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES
ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED
(I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR THE SECURITIES UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR (B)
AN OPINION OF COUNSEL TO THE HOLDER (IF REQUESTED BY THE COMPANY), IN A FORM REASONABLY ACCEPTABLE TO THE COMPANY, THAT REGISTRATION IS
NOT REQUIRED UNDER SAID ACT OR (II) UNLESS SOLD OR ELIGIBLE TO BE SOLD PURSUANT TO RULE 144 OR RULE 144A UNDER SAID ACT.

 

3.8 Cancellation
of Loan Agreements. Upon execution of this Agreement, the Investors acknowledge and agree that (i) all amounts due and owing by the
Company further to the Loan Agreement are satisfied in full and (ii) the Company has no further obligation or liability further to the
Loan Agreements.

 

3.9 Distribution of Shares.
Investors agree that in no event will one individual Investor at any time be issued in excess of 19.99% of the issued and outstanding
Common Stock of the Company as of the date hereof and that they will take any and all actions, including, without limitation, a distribution
to their members of Shares, to ensure that stockholder approval will be required by the applicable rules and regulations of the Nasdaq
Stock Market (or any successor entity) from the stockholders of the Company with respect to the transactions contemplated by the Transaction
Documents.

 

4.0             
Miscellaneous Provisions.

 

4.1             
Further Assurances. Each party agrees to cooperate fully with the other parties and to execute such further instruments,
documents and agreements and to give such further written assurances, as may be reasonably requested by any other party to better evidence
and reflect the transactions described herein and contemplated hereby, and to carry into effect the intents and purposes of this Agreement.

 

4.2             
Rights Cumulative. Each and all of the various rights, powers and remedies of the parties hereto shall be considered to
be cumulative with and in addition to any other rights, powers and remedies which such parties may have at law or in equity in the event
of the breach of any of the terms of this Agreement. The exercise or partial exercise of any right, power or remedy shall neither constitute
the exclusive election thereof nor the waiver of any other right, power or remedy available to such party.

 

4.3             
 Pronouns. All pronouns and any variations thereof shall be deemed to refer to the masculine, feminine or neuter, singular
or plural, as the identity of the person, persons, entity or entities may require.

 

     

     

    

 

4.4             
Notices. All notices, consents or demands of any kind which any party to this Agreement may be required or may desire to
serve on any other party hereto in connection with this Agreement shall be in writing and shall be delivered by personal service or overnight
courier, by telex or facsimile transfer, or by registered or certified mail, return receipt requested, deposited in the United States
mail with postage thereon fully prepaid, addressed: (a) if to the Company, at its address set forth on the signature page hereof;
or (b) if to an Investor, at Investor’s address as set forth on the signature page below. Service of any such notice or demand
so made by mail shall be deemed complete on the date of actual delivery as shown by the addressee’s registry or certification receipt
or at the expiration of the fourth (4th) business day after the date of mailing, whichever is earlier in time. Any party hereto
may from time to time by notice in writing served upon the others as aforesaid, designate a different mailing address or a different person
to which such notices or demands are thereafter to be addressed or delivered.

 

4.5             
Captions. Captions are provided herein for convenience only and they form no part of this Agreement and are not to serve
as a basis for interpretation or construction of this Agreement, nor as evidence of the intention of the parties.

 

4.6             
Severability. The provisions of this Agreement are severable. The invalidity, in whole or in part, of any provision of this
Agreement shall not affect the validity or enforceability of any other of its provisions. If one or more provisions hereof shall be so
declared invalid or unenforceable, the remaining provisions shall remain in full force and effect and shall be construed in the broadest
possible manner to effectuate the purposes hereof. The parties further agree to replace such void or unenforceable provisions of this
Agreement with valid and enforceable provisions which will achieve, to the extent possible, the economic, business and other purposes
of the void or unenforceable provisions.

 

4.7             
Attorneys’ Fees. In any action at law or in equity to enforce any of the provisions or rights under this Agreement,
the unsuccessful party to such litigation, as determined by the court in a final judgment or decree, shall pay the successful party all
costs, expenses and reasonable attorneys’ fees incurred by the successful party (including, without limitation, costs, expenses
and fees on any appeal).

 

4.8             
Counterparts. This Agreement may be executed in separate counterparts or by facsimile, each of which shall be deemed an
original, and when executed, separately or together, shall constitute a single original instrument, effective in the same manner as if
the parties hereto had executed one and the same instrument.

 

4.9             
Waiver. No waiver shall be effective unless in a writing signed by the person charged with making such waiver. Any waiver
of any term, provision or condition of this Agreement, whether by conduct or otherwise, in any one or more instances, shall not be deemed
to be, or be construed as, a further or continuing waiver of any such term, provision or condition or as a waiver of any other term, provision
or condition of this Agreement, unless it so provides by its terms.

 

     

     

    

 

4.10         
 Entire Agreement. This Agreement (together with its Exhibits and the other documents referred to herein, and except
as otherwise disclosed in such Exhibits and documents) is intended by the parties hereto to be the final expression of their agreement
and constitutes and embodies their entire agreement and understanding with regard to its subject matter and is a complete and exclusive
statement of the terms and conditions thereof, and shall supersede, merge and void any and all prior correspondence, conversations, negotiations,
agreements or understandings relating to such subject matter.

 

4.11         
Choice of Law. This Agreement shall be governed by and construed in accordance with the laws of the State of Delaware, without
regard to its conflict of laws rules or provisions.

 

4.12         
Binding on Heirs, Successors and Assigns. This Agreement and all of its terms, conditions and covenants are intended to
be fully effective and binding, to the extent permitted by law, on the heirs, executors, administrators, successors and permitted assigns
of the parties hereto.

 

4.13         
Survival. The respective representations and warranties given by the Company and the Investors, as contained herein and
in any certificates to be delivered at any Closing, shall survive such Closing Date without regard to any investigation made by any party.
All statements as to factual matters contained in any certificates, exhibits or other instruments delivered by or on behalf of any party
pursuant to the terms hereto or in connection with the transactions contemplated hereby shall be deemed, for all purposes, to constitute
representations and warranties by such party under the terms of this Agreement given as of the date of such certificate or instrument.

 

4.14         
Finder’s Fees. Each party represents that it is not and will not be obligated for any finder’s fee or commission
in connection with this transaction. Each Investor hereby agrees to indemnify and to hold harmless the Company from any liability for
any commission or compensation in the nature of a finder’s fee (and the costs and expenses of defending against such liability or
asserted liability) for which such Investor or any of its agents or representatives is responsible; and the Company agrees to indemnify
and hold harmless each Investor from any liability for any commission or compensation in the nature of a finder’s fee (and the costs
and expenses of defending against such liability or asserted liability) for which the Company or any of its officers, employees, agents
or representatives is responsible.

 

4.15         
Amendment. This Agreement shall be amended only upon the written consent of the Company and the Investors (or their permitted
assignees to whom Investors have expressly assigned their rights under this Agreement) holding at least a majority of the Shares (including,
for such purpose, any shares of Series A Preferred Stock and/or Common Stock issued upon conversion thereof) sold pursuant to this Agreement
and then held by such persons. Any party hereto may, as to itself, by a writing signed by an authorized representative of such party:
(a) extend the time for the performance of any of the obligations of another party; (b) waive any inaccuracies in representations
and warranties made by another party contained in this Agreement or in any documents delivered pursuant hereto; (c) waive compliance
by another party with any of the covenants contained in this Agreement or the performance of any obligations of such other party; or
(d) waive the fulfillment of any condition that is precedent to the performance by such party of any of its obligations under this
Agreement.

 

     

     

    

 

4.16         
Confidentiality. Each Investor (other than members of the Board of Directors of the Company) shall hold in confidence and
not disclose to any third party any nonpublic information concerning the Company obtained either in the course of the negotiation and
delivery of this Agreement and the agreements referred to herein or after the date hereof; provided, however, that the Investors
may make disclosure thereof to their respective professional advisors, as is required by any governmental authority or representative
thereof, or pursuant to legal process or in exercising their remedies hereunder, and shall require, to the extent permitted by applicable
law, any such third party to whom disclosure is made to agree to comply with this Section 6.16.

 

4.17         
Expenses. Each of the Company and the Investors shall bear their own expenses incurred with respect to this Agreement and
the transactions contemplated hereby.

 

[SIGNATURE PAGES FOLLOW]

 

     

     

    

 

IN WITNESS WHEREOF, the parties
hereto have executed this Agreement with the intent and agreement that the same shall be effective as of the day and year first above
written.

 

 

	 	DIGITAL BRANDS GROUP, INC.
	 	 
	 	By: 	/s/
John Hilburn Davis IV
	 	Name: 	John Hilburn Davis IV
	 	Title: 	Chief Executive Officer
	 	Address: 	1400 Lavaca Street, Austin, TX 78701
	 	 
	INVESTORS:	Bocm4-DSTLD-Senior Debt, LLC
	 	 
	 	 
	 	 /s/
Kurt Hanson
	 	Kurt Hanson
	 	 
	 	Address: 	 111 S Main Street, Suite 2025
	 	 	Salt Lake City, UT 84111

  

[Signature Page to Securities
Purchase Agreement]

 

     

     

    

 

Schedule I 

 

	Investors	Shares	Purchase Price
	
     

     

    Bocm4-DSTLD-Senior Debt, LLC

     

     

     
	6,300	$1,000 per share

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