<PAGE>

                                                                   Exhibit 10.44

                              SETTLEMENT AGREEMENT

         THIS SETTLEMENT AGREEMENT (this "Agreement") is entered into as of the
31st day of October, 2003 ("Effective Date") by and among TROPICAL SPORTSWEAR
INT'L CORPORATION, a Florida corporation ("Tropical") and GREGORY L. WILLIAMS
("Williams"). The term "Parties" refers to all of the foregoing, and the term
"Party" refers to each of the foregoing.

                  WHEREAS, Tropical and Williams are parties in a civil action
styled Tropical Sportswear Int'l Corporation vs. Christopher B. Munday, Gregory
L. Williams and Nelson L. McPherson, Jr., in the Circuit Court in and for the
Thirteenth Judicial Circuit of Hillsborough County, Florida, Case No: 03-7619,
Division I (the "Litigation"); and

                  WHEREAS, the Litigation pertains to Tropical's disputed
obligations to Christopher B. Munday ("Munday"), Williams and Nelson L.
McPherson, Jr. ("McPherson") resulting from Tropical's termination of the
employment of Munday, Williams and McPherson, effective August 15, 2003
("Termination Date"); and

                  WHEREAS, the Parties have successfully mediated a resolution
of the Litigation, the terms and conditions of which are embodied in this
Agreement; and

                  NOW, THEREFORE, in consideration of the payments and covenants
described below, and in consideration of other good and valuable consideration,
the receipt and sufficiency of all of which are hereby acknowledged, Tropical
and Williams agree as to the following terms and conditions:

         1.       The foregoing recitals are true and correct.

         2.A.     Tropical shall compensate Williams in the sum of One Million
                  Nine Hundred Twenty Six Thousand Dollars and No Cents
                  ($1,926,000.00). This entire amount of compensation is
                  severance for termination of his employment with Tropical and,
                  except as otherwise expressly stated hereunder, is in
                  fulfillment of all obligations of Tropical to Williams.

           B.     The amount of compensation set forth in paragraph 2.A. above,
                  shall be paid to Williams less all sums required to be
                  withheld by Tropical pursuant to federal, state, local and
                  foreign law or regulation. The withholding sum equals the
                  amount of Five Hundred Nine Thousand Four Hundred Twenty Seven
                  Dollars and No Cents ($509,427.00). Williams acknowledges
                  receipt of the sum of One Million Four Hundred Sixteen
                  Thousand Five Hundred Seventy Three and No Cents

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<PAGE>

                  ($1,416,573.00), which is the total compensation less the
                  withholding sum.

         3.A.     In addition, Tropical shall pay Williams the sum of One
                  Hundred Twenty Two Thousand Ninety Seven Dollars and Fifty Six
                  Cents ($122,097.56), as compensation "grossed up" for the
                  value of, and discharge of Tropical from any responsibility in
                  connection with, the following insurance:

<TABLE>
<CAPTION>
Type                       Policy Value              Carrier                   Annual Cost
----                       ------------              -------                   -----------
<S>                        <C>                       <C>                       <C>
Family PPO                  n/a                       Aetna                      $ 10,860

Group Life                  $ 500,000                 Aetna                      $ 14,955
</TABLE>

                  Tropical states that, in view of Williams' representation that
                  he intends to continue making payments on one or more of the
                  above insurances, Tropical at this time has no intention to
                  affirmatively terminate any of the insurance described above,
                  in order to permit Williams an opportunity to continue the
                  insurance and to pay for the insurance directly. Tropical at
                  this time does hope that it can change the billing to Williams
                  on the above insurance, and presently intends to attempt to do
                  so. Tropical, however, represents that it does intend to stop
                  in the near future any type of administrative work, including
                  the forwarding of any premium notices in connection with the
                  insurance. Williams shall be totally responsible for the
                  payment of insurance premiums for so long as he chooses to
                  maintain any of the above insurance. Tropical represents that,
                  should Williams fail to pay any premium due or payable,
                  whether now due and payable or due and payable in the future,
                  or should some other reason or circumstance exist or occur now
                  or in the future, any of the insurance may expire or terminate
                  at any time. Notwithstanding the above, and irrespective of
                  any intentions or hopes of Tropical, Tropical is hereby
                  discharged and released from any responsibility or duty of any
                  nature whatsoever with respect to the above insurance, and is
                  hereby discharged and released from any type of conduct, act,
                  omission or circumstance related to or arising from the above
                  insurance, whether related to or arising from contract, tort,
                  fraud, negligence, statute, regulation, duty, law, equity or
                  otherwise.

                  Withholding on this compensation equals Thirty Two Thousand
                  Two Hundred Ninety Four Dollars and Eighty Cents ($32,294.80).
                  Williams acknowledges receipt of the sum of Eighty Nine
                  Thousand Eight Hundred Two Dollars and Seventy Six Cents
                  ($89,802.76), which is the compensation less the withholding
                  sum.

           B.     For a period of three (3) years following Termination Date of
                  Williams, Tropical shall continue its practice of paying
                  "grossed up" the following insurance benefits for Williams:
                  (a) dental and life, and (b) disability as provided by
                  individual, but not

                                       2
<PAGE>

                  group, policies. The foregoing insurance and policies are
                  specifically described as follows:

<TABLE>
<CAPTION>
Type                       Policy Value                Carrier               Annual Cost
----                       ------------                -------               -----------
<S>                        <C>                       <C>                     <C>
Family Dental              n/a                       CompBenefits              $350.48

Individual Life            $1,000,000                C.N.A.                    $  1445

Executive Group
   Life                    $1,000,000                C.N.A.                    $  1375

Supplemental
   Disability              $5000/month               MetLife                   $  2662
                           $7100/month               Provident                 $ 2,110
</TABLE>

                  Tropical shall not unilaterally terminate any of the above
                  insurance.

           C.     In the event an insurer terminates and refuses to renew any of
                  the above insurance, other than as a result of Tropical's
                  nonpayment of premiums, Tropical shall in that event seek and
                  attempt to reasonably secure replacement coverage, reasonably
                  comparable to the terminated insurance, for the remaining part
                  of the three year period following Termination Date; provided,
                  however, in no event shall Tropical be obligated to secure
                  replacement insurance if the annual cost for the replacement
                  insurance is more than double the Annual Cost of the
                  terminated insurance. If Tropical takes steps to seek and
                  secure replacement coverage and, in its judgment exercised on
                  a reasonable basis, it cannot secure replacement insurance
                  under the foregoing terms, then in that event Tropical shall
                  stop payments to the insurer and make payment to Williams of
                  an amount equal to the sum of twice the remaining amount of
                  Annual Cost as set forth above plus gross up for taxes, for
                  the remaining part of the three year period and attributable
                  to the insurance so terminated.

           D.     During the remaining part of the three (3) year period
                  following Termination Date, Tropical shall take steps to
                  secure and pay for insurance reasonably comparable to the
                  following former insurance benefits of Williams:

<TABLE>
<CAPTION>
Type                       Policy Value              Carrier                  Annual Cost
----                       ------------              -------                  -----------
<S>                        <C>                       <C>                      <C>
Accidental Death
   & Dismemberment         $500,000                  Aetna                      $  120

Group Travel
   Accident                $3,000,000                Reliance Standard          $  120
                           in event of
                              death
</TABLE>

                                       3
<PAGE>

                  However, Tropical shall not be obligated to secure replacement
                  insurance if the annual cost for the replacement insurance is
                  more than double the Annual Cost of the terminated insurance.
                  If Tropical takes steps to seek and secure replacement
                  coverage and, in its judgment exercised on a reasonable basis,
                  it cannot secure replacement insurance under the foregoing
                  terms, then in that event Tropical shall stop payments to the
                  insurer and make payment to Williams of an amount equal to the
                  sum of twice the remaining amount of Annual Cost as set forth
                  above plus gross up for taxes, for the remaining part of the
                  three year period and attributable to the insurance not
                  replaced.

           E.     Tropical shall not be obligated to secure or provide
                  disability insurance for Williams or his family under any
                  group disability policy.

           F.     If Williams during the three year period after Termination
                  Date, becomes reemployed with a different employer and is
                  eligible to receive any medical or other benefits under that
                  employer's provided plan(s) comparable to the above, the
                  comparable medical and other benefits from Tropical and its
                  benefits providers shall be secondary to those provided by the
                  new employer(s) of Williams.

           G.     Tropical shall provide to Williams notice of any termination
                  of the above insurance.

         4.A.     The Parties mutually and generally release each other under
                  the following terms.

           B.     Unless specifically and expressly stated otherwise in this
                  Agreement, the term "Claims" as used in this Agreement
                  includes any and all rights to compensation, severance or
                  termination compensations, accrued obligations or benefits,
                  business reason termination payments, target annual cash
                  bonuses, welfare plan benefits, other benefits, actions,
                  causes of action, defenses, lawsuits, arbitrations, injuries,
                  losses, payments, attorneys' fees, benefits, rights, damages,
                  costs, loss of service, loss of opportunities, loss of
                  profits, liens, expenses, compensation, suits, debts, dues,
                  sums of money, accounts, reckonings, bonds, stock claims,
                  stock option claims, benefits claims, bills, securities,
                  specialties, covenants, contracts, controversies, agreements,
                  promises, duties and obligations, variances, judgments,
                  extents, executions, claims, and demands, of any type
                  whatsoever, including any claim for indemnity or for
                  contribution, or any claim in subrogation or other similar
                  third party type of claim, in law or equity, whether known or
                  unknown, suspected or unsuspected, actual or potential,
                  asserted or unasserted, warranted or unwarranted, fixed or
                  contingent, liquidated or unliquidated, which has matured and
                  which a Party has as of the effective date of this Agreement,
                  or had or ever had prior to the effective date of this
                  Agreement.

                                       4
<PAGE>

           C.     The term "Claims" shall also include, but is not limited to,
                  any cause of action or any matter whatsoever relating to,
                  arising from, or in any way pertaining to the Litigation, or
                  relating to, arising from, or in any way pertaining to any
                  matter which was alleged in, or which could have been alleged
                  in, the Litigation.

           D.     The term "Claims" shall also include, but is not limited to,
                  any cause of action, charges, claims, actions, causes of
                  action or liabilities of any kind or nature, whether known or
                  unknown, related to or arising out of employment and/or
                  association of Williams or with Tropical that they have ever
                  had or now have, or that any person or entity claiming through
                  them may have or claim to have, whether based on tort,
                  contract (express or implied) or any federal, state or local
                  law, statute or regulation, including, but not limited to any
                  claim under the Employee Retirement Income Security Act, 29
                  U.S.C. Section 1001 et seq.; the Family and Medical Leave Act,
                  29 U.S.C. Section 2611 et seq.; Consolidated Omnibus Budget
                  Reconciliation Act of 1986, "COBRA," 29 U.S. C. Section 1161
                  et seq.; Title VII of the Civil Rights Act of 1964, 42. U.S.C.
                  Section 2000 et seq., as amended; the Americans With
                  Disabilities Act (ADA), 42 U.S.C. Section 12101 et seq.; the
                  Florida's Whistleblower Statute, Fla. Stat. Ann. Section
                  448.101 et seq.; the Fair Labor Standards Act; the Florida
                  Civil Rights Act, Fla. Stat. Ann. Section 760.10 et seq. or
                  any similar state or local laws or ordinances prohibiting
                  discrimination, harassment or retaliation; any other claims
                  for personal injury, emotional distress, negligence, breach of
                  fiduciary duty, fraud, worker's compensation, invasion of
                  privacy, defamation, compensatory damages, punitive damages,
                  attorney's fees or costs; and any claims to incentive payments
                  or bonuses.

           E.     Notwithstanding the above, the term "Claims" does not include,
                  and specifically excludes, any obligation of Tropical to
                  indemnify Williams under By-Laws of Tropical, and any
                  obligation under this Agreement.

           F.     The releases set forth in this Agreement shall become
                  effective as of the Effective Date specified above, upon the
                  execution of this Agreement by all Parties.

           G.     Williams and Tropical voluntarily and knowingly release and
                  discharge from any Claims, jointly and severally, each other
                  and each other's current, former and future agents, attorneys,
                  heirs, representatives, executors, employees, officers,
                  directors, partners, trustees, shareholders, subsidiaries,
                  successors, assigns, affiliates, beneficiaries, insurers,
                  sureties, indemnitors, guarantors, benefit or compensation
                  plans, and their respective current, former and future agents,
                  attorneys, heirs, representatives, executors, employees,
                  officers, directors, partners, trustees, shareholders,
                  subsidiaries, successors, assigns, affiliates, beneficiaries,
                  insurers, sureties, indemnitors, guarantors, and benefit or
                  compensation plans.

           H.     Williams and Tropical voluntarily and knowingly terminate any
                  employment

                                       5
<PAGE>

                  agreements between them including, but not limited to, the
                  following documents bearing signatures of Williams and
                  Tropical: (i) a document, dated April 15, 2002, entitled
                  "Employment Agreement"; and (ii) a separate document dated
                  July 1, 1999, entitled "Employment Agreement."

           I.     Williams represents that he has not filed any complaint, claim
                  or charge against Tropical with the Equal Employment
                  Opportunity Commission, Florida Commission on Human Relations,
                  the Federal or Florida Department of Labor, or with any other
                  local, state or federal agency or court. Williams agrees that,
                  if any such agency or court assumes the prosecution or
                  jurisdiction of any complaint or charge against Tropical,
                  Williams will immediately dismiss the complaint or charge
                  and/or will immediately request such agency or court to
                  dismiss and withdraw from the matter. In the event Williams
                  fails or refuses to undertake these obligations, Williams
                  agrees that this Agreement shall operate to effect Williams'
                  dismissal or withdrawal of such complaint, charge or claim and
                  that Williams will forward to Tropical any monies Williams
                  receives from such complaint, charge or claim.

           J.     The Parties represent and warrant that any Claim owned or held
                  by them at any time has not been assigned and has not been
                  transferred to any other person or entity.

           K.     The release of this Agreement evidences settlement of claims
                  which are disputed both as to liability and as to amount, and
                  the consideration recited above shall not be construed as an
                  admission of liability, as the same is now and has been
                  expressly denied.

           L.     Tropical shall remain obligated to indemnify Williams for any
                  Excise Tax "grossed up" and any related taxes, interest,
                  penalties and costs, including attorneys fees, imposed upon
                  Williams under Section 4999 of the Internal Revenue Code or
                  related sections as a result of any payment made to Williams
                  under this Agreement.

         5.       All vested or non-vested options of Williams to purchase
                  stock, or to purchase any type of equity, debt, security or
                  other type of right or obligation, in or issued by Tropical,
                  are cancelled as of the Effective Date. Williams represents he
                  has exercised no such options on or after Wednesday, October
                  8, 2003.

         6.       For three (3) years after the Termination Date, Williams shall
                  not solicit for hire any individual who was an employee of
                  Tropical on the Effective Date.

         7.       Williams shall cooperate with Tropical and its counsel in
                  respect to any lawsuits, proceedings, investigations or other
                  types of actions involving Tropical, and shall provide and
                  deliver to Tropical and its counsel at reasonable times and
                  places, upon reasonable request of Tropical, truthful
                  information, and originals or duplicates of

                                       6
<PAGE>

                  documents or information whether electronic or otherwise,
                  within the custody, possession or control of Williams in
                  respect to any such lawsuits, proceedings, investigations, or
                  other types of actions, or in relation to Tropical.

         8.       The Litigation shall be immediately dismissed with prejudice
                  by stipulation of the parties in the Litigation.. A copy of
                  the Stipulation for Dismissal With Prejudice is attached as
                  Exhibit A.

         9.       Tropical is bound by an obligation of indemnity and of
                  advancement of expenses to the fullest extent permitted by the
                  law of the State of Florida, as the same may be in effect from
                  time to time, and as provided in its Bylaws, and as defined
                  and set forth in correspondence of Tropical to Williams dated
                  October 28, 2003.

         10.      Tropical and Williams agree that each has reviewed this
                  Agreement and any rule of construction to the effect that
                  ambiguities are to be resolved against the drafter shall not
                  apply to the interpretation of this Agreement.

         11.      Tropical and Williams agree that they have each relied
                  exclusively upon independent counsel in connection with this
                  Agreement, which has been completely read and is readily
                  understood and voluntarily accepted.

         12.      In the event of breach of this Agreement by either Party, the
                  other Party shall be entitled at its option to seek the remedy
                  of specific performance exclusively before a state or federal
                  court of competent jurisdiction in Hillsborough County,
                  Florida.

         13.      This Agreement may be executed by any Party by execution of a
                  counterpart. A signature of a Party shall be effective by that
                  Party faxing or delivering a copy of the signed counterpart to
                  the other Party.

         14.      Except as otherwise expressly provided herein, and except for
                  the obligation of indemnity or advancement of expenses
                  referenced above, this Agreement contains the entire agreement
                  between the Parties and is only subject to modification by
                  written instrument signed by the Parties. No representation or
                  statement not contained herein, shall be binding on the
                  Parties.

         15.      The Parties agree that no inducements, statements or
                  representations have been made that are not set forth in this
                  Agreement and that the Parties did not rely upon any
                  inducements, statements or representations not set forth
                  herein.

         16.      This Agreement was negotiated and delivered within the state
                  of Florida, and shall be governed by Florida law.

         17.      Tropical represents and warrants to Williams that the officer
                  executing this

                                       7
<PAGE>

                  Agreement has the requisite corporate authority to do so after
                  receiving all necessary and appropriate approvals.

         18.      Williams is aware that this Agreement has significant legal
                  meaning, and he enters into this Agreement freely and
                  voluntarily.

                                       8
<PAGE>

         IN WITNESS WHEREOF, the parties have executed and delivered this
Agreement as of the day and year indicated above.

      Signed this 31st day of October, 2003.

WILLIAMS                                        TROPICAL

/s/ Gregory L. Williams                         /s/ Michael Kagan
-----------------------------                   ----------------------------
Gregory L. Williams                             Michael Kagan
                                                Chief Executive Officer
Address:                                        Tropical Sportswear Int'l
19297 Ayers Road                                Corporation
Brooksville, Florida 34604

                                       9
<PAGE>

                                    EXHIBIT A

             IN THE CIRCUIT COURT OF THE THIRTEENTH JUDICIAL CIRCUIT
                     IN AND FOR HILLSBOROUGH COUNTY, FLORIDA
                                 CIVIL DIVISION

TROPICAL SPORTSWEAR
INT'L CORPORATION,

                  Plaintiff,

vs.                                                         Case No: 03-7619
                                                            Division:      I

CHRISTOPHER B. MUNDAY,
GREGORY L. WILLIAMS and
NELSON L. MCPHERSON, JR.,

                     Defendants.

___________________________________/

                     STIPULATION OF DISMISSAL WITH PREJUDICE

         Plaintiff and Defendants, by undersigned counsel and pursuant to Fla.
R. Civ. P. 1.420(A)(1), stipulate to dismissal with prejudice of this action,
with each such party to bear that Party's own fees and costs.

         Dated as of _____________________, 2003.

Leslie Joughin, III, FBN: 339385                Lawrence P. Ingram, FBN:
855510
Charles F. Ketchey, FBN: 0181735            PHELPS DUNBAR LLP
Joseph W. N. Rugg, FBN: 335096              100 S. Ashley Drive
S. Gordon Hill, FBN: 094374                        Suite 1900
AKERMAN SENTERFITT                                    Tampa, Florida  33602-5311
100 S. Ashley Dr., Suite 1500                      Tel:  813-472-7550
Post Office Box 3273 (Zip 33601)            Fax: 813-472-7570
Tampa, Florida  33602                             Attorney for Defendant,
Tel: 813-223-7333/Fax: 813-223-2837         Nelson L. McPherson, Jr.
Attorneys for Plaintiff

                                       10
<PAGE>

David P. Rankin, FBN:  ________            Michael C. Addison, FBN:  0145579
14502 N. Dale Mabry                                 ADDISON & DELANO, P.A
Suite 300                                                  Post Office Box 2175
Tampa, FL  33618                                    Tampa, FL 33601-2175
Tel: 813-968-6633                                   Tel: 813-223-2000
Fax: 813-963-2175                                   Fax: 813-228-6000
Attorney for Defendant,                        Attorney for Defendant,
 Christopher B. Munday                         Gregory L. Williams

                             CERTIFICATE OF SERVICE

         I HEREBY CERTIFY that a true and correct copy of the foregoing has been
furnished via U.S. Mail to Lawrence P. Ingram, Esquire, Phelps Dunbar LLP, 100
S. Ashley Dr., Suite 1900, Tampa, Florida 33602-5311; Jeffrey A. Aman, Esquire,
Aman Law Firm, 14502 N. Dale Mabry, Suite 300, Tampa, Florida 33618; Michael C.
Addison, Esquire, Addison & Delano, P.A., Post Office Box 2175, Tampa, Florida
33601-2175, and Leslie Joughin, III, Charles F. Ketchey, Joseph W. N. Rugg, and
S. Gordon Hill, Akerman Senterfitt, Post Office Box 3273, Tampa, Florida
33601-3273 this ____ day of _______, 2003.

                                        _____________________________________
                                                                     Attorney

                                       11