CLICK TO EDIT MASTER TITLE STYLE

Investor Presentation

October 15, 2018

October 15, 2018

CLICK TO EDIT MASTER TITLE STYLE
Cautionary Note Regarding Forward-Looking Statements

• This presentation contains forward-looking information, including the Company’s statements regarding its future outlook. In addition,
words such as “expects,” “assumes,” “anticipates,” “envisions,” “targets,” “goals,” “projects,” “intends,” “plans,” “believes,” “seeks,”
“estimates,” “guidance,” “may,” “projections,” and “business outlook,” variations of such words and similar expressions are intended to
identify such forward-looking statements. The forward-looking statements are made pursuant to the Safe Harbor provisions of the
Private Securities Litigation Reform Act of 1995. Any forward-looking statements that we make herein are not guarantees of future
performance and actual results may differ materially from those in such forward-looking statements as a result of various
factors. Factors that might cause or contribute to such differences include, but are not limited to: actions or inactions by governmental
entities; domestic and international macro-economic conditions; inflation or deflation; the loss of, or changes in, key personnel; success,
or lack thereof, in formulating or executing our internal strategies and operating plans including new store and new market expansion
plans; cost reduction initiatives and revenue enhancement strategies; changes in demand for clothing or rental product; market trends
in the retail business; customer confidence and spending patterns; changes in traffic trends in our stores; customer acceptance of our
merchandise strategies including custom clothing; performance issues with key suppliers; disruptions in our supply chain; severe
weather; foreign currency fluctuations; government export and import policies, including the enactment of duties or tariffs; advertising
or marketing activities of competitors; the impact of cybersecurity threats or data breaches; and legal proceedings.
• Forward-looking statements are intended to convey the Company’s expectations about the future, and speak only as of the date they
are made. We undertake no obligation to publicly update or revise any forward-looking statements that may be made from time to
time, whether as a result of new information, future developments or otherwise, except as required by applicable law. However, any
further disclosures made on related subjects in our subsequent reports on Forms 10-K, 10-Q and 8-K should be consulted. This
discussion is provided as permitted by the Private Securities Litigation Reform Act of 1995, and all written or oral forward-looking
statements that are made by or attributable to us are expressly qualified in their entirety by the cautionary statements contained or
referenced in this section.

October 15, 2018 2

CLICK TO EDIT MASTER TITLE STYLE
Agenda

1 Business Overview

2 Growth Strategy

3 Key Financial Highlights

4 Appendix - Non-GAAP Reconciliations

October 15, 2018 3

CLICK TO EDIT MASTER TITLE STYLE

Business Overview

October 15, 2018

CLICK TO EDIT MASTER TITLE STYLE
CLICK TO EDIT MASTER TITLE STYLE
Differentiated Market Leader in Men’s Tailored Clothing

1 Market leading specialty retailer of men’s tailored clothing in U.S. and Canada

2 Expert service and personalized products drive superior customer experience

3 Convenient omni-channel network makes shopping easy

4 Compelling strategies to drive sales and EPS growth

5 Focus on shareholder value creation through disciplined capital allocation

October 15, 2018 5

CLICK TO EDIT
Market MASTER
Leading TITLE STYLE
Specialty Retailer in Attractive Category

Menswear U.S. Menswear Market

($ in BN)
• The U.S. menswear market is large
and stable with over $85BN in sales in
$101
2017
$98
• The men’s segment is less exposed to $94
fashion risk than other apparel $91
categories
$88
• Men’s suiting requires the need for $85
optimal fit, which provides an
inherent defense against pure online
players
Formal Tailored Polished Casual 2017 2018 2019 2020 2021 2022

Source: Euromonitor

October 15, 2018 6

 CLICK TO
Expert EDIT MASTER
Stylists TITLEGive
and Tailors STYLE
Men a Reason to Shop in Person

Men Want Help Putting Outfits Together

Experienced wardrobe consultants and tailors help men

feel confident and love the way they look.
They help men:
 Find the right fit
 Complete the outfit
 Tailor exact measurements
October 15, 2018 7
 CLICK TO EDIT Exclusive
Personalized, MASTER TITLE STYLE Keep Men Coming Back
Products

The Custom Experience Performance Exclusives

• We make buying a • Performance fabrics
custom suit as easy increasingly popular
and affordable to • Temperature
buy as a suit off the regulating Kenneth
rack Cole AWEARTECH
• More than doubled exclusively at Men’s
custom sales in FY17 Wearhouse and
to over $100 million; TravelTech at Jos. A.
1H 2018 run rate of Bank
$4mm per week • Performance fabric
• Best-in class delivery custom suits
speeds introduced in 2018

Men’s Wearhouse and Jos. A. Bank offer 70% and 95% exclusive brands, respectively.
October 15, 2018 8
CLICK TO EDIT MASTER TITLE STYLE
Store Located within 10 Miles of 70% of U.S. & Canada Customers

2Q FY 2018 Footprint – 1,469 Stores1 2Q FY18 Store Count by Brand

K&G
2
88
16
1
Moores
15 126
2
5

23 54 25 Men’s
1
2 3 4 Wearhouse
13
4
3
2 7681 Jos. A. Bank
21 1
2 9 487
1 18 72 45
49
9 7 11 24 5
11 64 47
113 52 5
25
24
62 26 5 48
14 5
14 50
22
25 48
6 11 8
22
9 22 47
121 20

93

1
85%
of stores located in strip or
power centers, not malls
Source: Company filings as of 9/12/18; 1 Includes one Joseph Abboud store in New York and 49 Men’s Wearhouse and Tux stores

October 15, 2018 9

CLICK TO EDITOmni-Channel
Convenient MASTER TITLE STYLE
Network Makes Shopping Easy

Comprehensive Omni-Channel Capabilities Across Formats

 Same day shipping

 Ship to store

 Mobile app

 Reserve online, pick up

in store

 Ship from store

 Int’l shipping to >100

countries

October 15, 2018 10

CLICK TO EDIT MASTER TITLE STYLE

Growth Strategy

October 15, 2018

CLICK TO EDIT MASTER TITLE STYLE
CLICK TO EDIT MASTER TITLE STYLE
Three Key Growth Strategies

1 Expand custom clothing business – disrupt the mass market for suits

2 Elevate the brand promise and enhance marketing effectiveness

3 Enhance omni-channel experience – make shopping easier, more personalized

October 15, 2018 12

 CLICK TO EDIT Custom
Multi-Pronged MASTER TITLE
GrowthSTYLE
Strategy With Large Addressable Market

Launch New
Products

Attract New
Customers

Improve
Delivery Speed

Increase Penetration
2017 with Existing Customers
$100M+
Up >100%
y-o-y

October 15, 2018 13

 CLICK TO
Custom EDIT MASTER
Enhances TITLE STYLEExperience; Increases Operating Profit
the Customer

 Higher Average Unit Retail

 Higher Gross Margin Dollars

 Greater Customer Frequency

Higher Average Annual Spend



 Greater Inventory Efficiency

October 15, 2018 14

CLICK TO EDIT
Marketing MASTER Driving
Strategy TITLE STYLE
New-to-File Customers

Shift Messaging Mix to Shift Channel Mix to

More Branding vs. Promotion More Digital vs. Broadcast

• New branding campaigns launched in August • TTM 2Q 2018 advertising expense down 30
2017 for Men’s Wearhouse, June 2018 for Jos. basis points as a percent of sales, reflecting
A. Bank more efficient mix of broadcast and digital

• Elevated story-telling about what our brands • Social media and videos complement
stand for and offer our customers broadcast campaigns

• Generated lift in New-To-File customers for • Digital marketing (SEM, SEO, email) driving
both brands traffic to stores and e-commerce sites

October 15, 2018 15

 CLICK TO EDIT MASTER
Omni-Channel TITLE
Approach STYLECustomers Wherever They Want to Shop
Serves

• Launched LIVE! online service that connects e-commerce shoppers with in-store
sales associates
• Sales associates use live chat, and photo and video sharing to help guide shoppers
• 1,600+ sales associates actively engaging with customers as of September 2018
• Driving increased average order values and conversion rates

65 Million Visits to e-Commerce Sites in FY 2017, up 8% Y-o-Y

October 15, 2018 16
CLICK TO EDIT MASTER TITLE STYLE

Financial Highlights

October 15, 2018

 CLICK TO
Strong EDIT
Free MASTER
Cash FlowTITLE
andSTYLE
Focus on Debt Reduction

($ in mm)
Free Cash Flow 1 Total Debt2
$323
$1,656 $1,596
$256 $1,397
$1,216

$143

$16
2015 2016 2017 2Q 2018
2015 2016 2017 TTM 2Q 2018
Total liquidity3 4.6x 4.7x 3.9x 3.5x

$609 Debt / LTM Adjusted EBITDA4

$451 $486
$400
• During FY16 through 2Q 2018, reduced debt balance by
$440mm
• Sr. notes reduced by $371mm, including partial
redemption of $175mm (2Q 2018) using cash and ABL
• Free cash flow has increased from $16mm at FY15 to
2015 2016 2017 2Q 2018 $323mm at TTM 2Q 2018
Source: Company filings
1 Calculated as (Cash from operations – Capital Expenditures); see appendix for reconciliation
2Calculated net of deferred financing costs and OID
3 Calculated as (Cash + Undrawn R/C availability)
4Calculated as Total Debt/(Adjusted EBIT + Depreciation and Amortization)

October 15, 2018 18

 CLICK
Cost TO EDIT MASTER
Structure ReflectsTITLE STYLEStore Fleet and SG&A Savings
Smaller

TLRD has completed a store rationalization plan and profit improvement program targeting SG&A cost reduction

Adjusted SG&A1 Expense / % of Sales Store Count

36.0% 1,724
35.8%
1,667

35.1%
34.9% 1,477 1,469

2015 2016 2017 TTM 2Q 2018 2015 2016 2017 2Q 2018

Source: Company filings

1 Includes advertising expense

October 15, 2018 19

 CLICK TO EDIT
Historical MASTER
Comp TITLE
Sales STYLE
by Brand

Comparable sales by brand

FY FY FY
Q1 Q2 Q3 Q4 2015 Q1 Q2 Q3 Q4 2016 Q1 Q2 Q3 Q4 2017 Q1 Q2

6.8% 3.1% 5.3% 4.3% 4.9% (3.5)% 2.9% 0.1% (2.2)% (0.6)% (3.1)% (2.2)% (1.0)% 2.3% (1.1)% 3.2% 1.0%

(1.1)% (9.0)% (14.4)% (32.3)% (16.3)% (16.0)% (16.3)% (9.8)% 3.6% (9.5)% 3.5% 7.8% 4.9% 5.3% 5.4% 1.2% 2.0%

7.3% 6.7% 3.7% 1.9% 5.0% 0.2% (2.2)% (3.0)% (5.2)% (2.4)% (7.4)% (1.7)% (0.6)% (1.7)% (3.1)% (1.7)% 3.5%

0.8% 0.7% (5.4)% (2.7)% (1.7)% (3.9)% (1.5)% (0.4)% (5.4)% (2.6)% (5.3)% 0.3% (2.6)% (1.4)% (2.0)% 1.8% 3.7%

Overall Retail
4.4% 0.0% (1.1)% (10.6%) (2.0%) (6.2)% (2.8)% (2.6)% (1.2)% (3.2)% (2.4)% 0.1% 0.1% 2.5% 0.1% 2.1% 1.7%
segment

5 consecutive quarters of positive comps

Positive Comps for All Brands in 2Q 2018

Source: Company information and filings

October 15, 2018 20

 CLICK TO EDIT
Historical MASTEROverview
Financial TITLE STYLE

($ in mm)
Revenue Adj. EPS2
1
MW Jos. A. Bank K&G Moores Other $2.32
$3,496
$2.20
$3,379 $3,304 $3,312
277 $1.80 $1.79
223 314 286 275
338 215 216 223
330 324 322
867 750 735 735

1,791 1,771 1,743 1,757

2015 2016 2017 TTM 2Q 2018 2015 2016 2017 TTM 2Q 2018

($ in mm)
Adj. Gross Margin2 Adj. EBITDA2

42.9% 42.6% 42.7% 42.2%

$359 $355
$337 $346

2015 2016 2017 TTM 2Q 2018 2015 2016 2017 TTM 2Q 2018

Source: Company filings

Note: 1 Includes Corporate Apparel and MW Cleaners (which was sold in March 2018 for $18mm); 2 Adjusted EPS, Gross Margin and EBITDA reconciliation at the end of this presentation

October 15, 2018 21

CLICK Financial
2018 TO EDIT MASTER TITLE STYLE
Priorities

Execute growth initiatives to increase market share and drive positive

1
comparable sales performance

Maintain healthy gross margin rate through disciplined promotional activity

2
and sales from exclusive merchandise

3 Continue to focus on improving cost structure

4 Reduce interest expense with continued focus on debt pay down

Generate strong cash flow from operations through improved working capital
5
management and unlocking additional cost savings

Invest capex to support growth initiatives; maintain dividend and use

6
remaining free cash flow to pay down debt

October 15, 2018 22

 CLICK
FY TO EDIT
2018 MASTER
Outlook 1 TITLE STYLE

Adjusted Diluted EPS $2.35 to $2.50

- Up low-single-digit %
Retail Comp Sales
- Flat-to-up-slightly

Effective Tax Rate ~25%

Store Closures ~Net 10

Inventory Down high-single-digit %

Capital Expenditures ~$100 million

Depreciation &
~$100 million
Amortization
Source: Company information and filings; 1FY 2018 Outlook as of September 12, 2018

October 15, 2018 23

CLICK TO EDIT MASTER TITLE STYLE

APPENDIX

GAAP/NON-GAAP RECONCILIATIONS

October 15, 2018

CLICK TO
GAAP toEDIT MASTER TITLE
Non-GAAP STYLE
Reconciliations – TTM 2Q 2018

Closure of Rental Partial

Divestiture of Product Distribution Refinancing of Redemption of Total Non-GAAP
($ in thousands, except per share amounts) GAAP Results MW Cleaners (1) Center (2) Term Loan (3) Senior Notes (4) Adjustments Adjusted Results
GAAP to Non-GAAP Adjusted Statement of Earnings for TTM Q218:
$ 343,007 $ - $ 4,010 $ - $ - $ 4,010 $ 347,017
Rental services gross margin

1,327,027 4,010 1,331,037

Total retail gross margin - 4,010 - -
1,393,756 4,010 1,397,766
Total gross margin - 4,010 - -
Adjusted GM 42.2%

991,760 (5,266) (5,631) 986,129

Selling, general and administrative expenses (365) - -

230,832 5,266 4,375 9,641 240,473

Operating income - -

(19,384) 11,858 8,122 19,980 596

(Loss) gain on extinguishment of debt - -

Provision for income taxes(5) 19,985 12,401 32,386

Net earnings 99,540 17,222 116,762

$ 1.98 $ 0.34 $ 2.32

Net earnings per diluted common share

(1) Consists of a $3.8 million loss upon divestiture of MW Cleaners business and a $1.5 million goodwill impairment charge, all related to the retail segment.
(2) Consists of $4.0 million of rental product writeoffs, $0.2 million of accelerated depreciation and $0.2 million of severance costs, all related to the retail segment.
(3) Consists of the elimination of unamortized deferred financing costs and original issue discount related to the refinancing of the Term Loan totaling $11.9 million.
(4) Consists of the $6.1 million premium and elimination of unamortized deferred financing costs totaling $2.0 million related to the partial redemption of senior notes.
(5) The tax effect of the excluded items is computed as the difference between tax expense on a GAAP basis and tax expense on an adjusted non-GAAP basis.

Source: Company Filings

October 15, 2018 25

CLICK TO
GAAP toEDIT MASTER TITLE
Non-GAAP STYLE
Reconciliations – FY17

Macy's Divestiture of MW Total Non-GAAP

($ in thousands, except per share amounts) GAAP Results Termination(1) Cleaners(2) Adjustments Adjusted Results

GAAP to Non-GAAP Adjusted Statement of Earnings for FY17:

Rental services gross margin $ 358,382 $ 1,416 $ - $ 1,416 $ 359,798

Total retail gross margin 1,342,961 1,416 - 1,416 1,344,377

Total gross margin 1,408,766 1,416 - 1,416 1,410,182
Adjusted GM 42.7%
Selling, general and administrative expenses 1,000,892 (15,736) - (15,736) 985,156
Goodwill impairment charge 1,500 - (1,500) (1,500) -

Operating income 229,416 17,152 1,500 18,652 248,068

Provision for income taxes(3) 38,251 6,756 45,007

Net earnings 96,703 11,896 108,599

Net earnings per diluted common share allocated to common $ 1.95 $ 0.25 $ 2.20
shareholders

(1) Consists of $12.3 million of termination costs, $1.4 million of rental product write-offs, $1.2 million of asset impairment charges and $2.3 million of other costs, all related to
the retail segment.
(2) Consists of a $1.5 million goodwill impairment charge for MW Cleaners and related to the retail segment.
(3) The tax effect of the excluded items is computed as the difference between tax expense on a GAAP basis and tax expense on an adjusted non-GAAP basis. The adjusted non-
GAAP rate also excludes one-time items primarily related to a favorable tax resolution of $18.3 million offset by a change in our position on permanently reinvested foreign
earnings and other impacts of the recently enacted Tax Cuts and Jobs Act of 2017 totaling $17.2 million.
Source: Company Filings

October 15, 2018 26

CLICK TO
GAAP toEDIT MASTER TITLE
Non-GAAP STYLE
Reconciliations – FY16

Jos. A. Bank Profit Total Non-GAAP

($ in thousands, except per share amounts) GAAP Results Integration(1) Improvement(2) Other(3) Adjustments Adjusted Results

GAAP to Non-GAAP Adjusted Statement of Earnings for FY16:

Retail clothing product gross margin $ 1,352,283 $ - $ - $ (23) $ (23) $ 1,352,260
Rental services gross margin 374,680 - - 1,069 1,069 375,749
Alteration and other services gross margin 58,131 - 255 - 255 58,386
Occupancy costs (431,298) 2,126 (4,109) (564) (2,547) (433,845)

Total retail gross margin 1,353,796 2,126 (3,854) 482 (1,246) 1,352,550
Total gross margin 1,441,468 2,126 (3,854) 482 (1,246) 1,440,222
Adjusted GM 42.6%
Selling, general and administrative expenses 1,099,328 (6,656) (69,848) (1,754) (78,258) 1,021,070
Asset impairment charges 19,358 - (2,093) (17,265) (19,358) -

Operating income(4) 132,826 8,782 68,087 19,501 96,370 229,196

Gain on extinguishment of debt, net(5) 1,737 (1,737) (1,737) -

Provision for income taxes(6) 6,625 33,436 40,061

Net earnings 24,956 61,197 86,153

Net earnings per diluted common share allocated to common

$ 0.51 $ 1.28 $ 1.79
shareholders
(1) Primarily consists of severance costs and accelerated depreciation.
(2) Primarily consists of $43.1 million of lease termination costs, $15.1 million of consulting costs and $6.1 million of severance costs.
(3) Primarily consists of asset impairment charges related to Macy's and severance costs.
(4) Of the $96.4 million in total adjustments to operating income, $69.9 million relates to the retail segment and $26.5 million relates to shared services.
(5) Recast to remove adjustments previously made for gains/losses on extinguishment of debt, which changes non-GAAP diluted EPS to $1.79 from $1.76.

(6) The tax effect of the excluded items is computed as the difference between tax expense on a GAAP basis and tax expense on an adjusted non-GAAP basis. Source: Company Filings
October 15, 2018 27
 CLICK TO
GAAP toEDIT MASTER TITLE
Non-GAAP STYLE
Reconciliations – FY15

Purchase Goodwill &

Acquisition and Accounting Profit Intangible Asset Total Non-GAAP
($ in thousands, except per share amounts) GAAP Results Integration(1) Allocation(2) Improvement(3) Impairments(4) Other(5) Adjustments Adjusted Results

GAAP to Non-GAAP Adjusted Statement of Earnings for FY15:

$ 1,439,611 $ 63 $ 969 $ 11,009 $ - $ - $ 12,041 $ 1,451,652
Retail clothing product gross margin
(455,486) 804 1,610 - 2,414 (453,072)
Occupancy costs - -

1,414,087 867 2,579 11,009 14,455 1,428,542

Total retail gross margin - -
1,484,423 867 2,579 11,009 14,455 1,498,878
Total gross margin - -
Adjusted GM 42.9%
1,085,900 (17,836) (8,121) (1,775) (30,800) 1,055,100
Selling, general and administrative expenses - (3,068)
1,243,354 - (5,533) (1,237,821) (1,243,354)
Goodwill and intangible asset impairment charges - - -
27,480 - (23,146) (4,074) (27,220)
Asset impairment charges - - -

Operating income(6) (1,077,296) 18,703 10,700 41,463 1,237,821 7,142 1,315,829 238,533

(12,675) 12,675 12,675

Loss on extinguishment of debt -

Provision for income taxes(7) (169,042) 214,148 45,106

Net earnings (1,026,719) 1,114,356 87,637

Net earnings per diluted common share allocated to common

$ (21.26) $ 23.06 $ 1.80
shareholders
(1) Acquisition & integration primarily relates to Jos. A. Bank.

(2) Consists of depreciation and amortization adjustments resulting from the recognition of intangible assets and step up in fair value for PP&E for Jos. A. Bank.
(3) Consists of $28.7 million in intangible and other asset impairment charges, $11.0 million of inventory write-downs and $1.8 million of consulting costs.
(4) Consists of asset impairment charges related to Jos. A. Bank with $769.0 million for goodwill, $425.9 million for trade name, $41.5 million for customer relationships and $1.4 million for favorable leases.

(5) Primarily consists of $4.1 million in store impairment charges.

(6) Of the $1,315.8 million in total adjustments to operating (loss) income, $1,310.9 million relates to the retail segment and $4.8 million relates to shared services.

(7) The tax effect of the excluded items is computed as the difference between tax expense on a GAAP basis and tax expense on an adjusted non-GAAP basis.
Source: Company Filings

October 15, 2018 28

CLICK TO
GAAP toEDIT MASTER TITLE
Non-GAAP STYLE
Reconciliations – Adjusted EBITDA

($ in millions) 2015 2016 2017 TTM Q2 2018

Adjusted EBITDA Reconciliation:
Net Earnings ($1,026.7) $25.0 $96.7 $99.5
Plus: Provision for Income Taxes (169.0) 6.6 38.3 20.0
Plus: Interest Expense 106.0 103.1 100.5 92.5
Less: Gain (Loss) on Extinguishment of Debt (12.7) 1.7 5.5 (19.4)
Less: Interest Income 0.2 0.2 0.6 0.6

EBIT ($1,077.3) $132.8 $229.4 $230.8

Plus: Acquisition & Integration Charges for Jos. A. Bank 18.7 0.0 0.0 0.0
Plus: Purchase Accounting Allocation Charges 10.7 0.0 0.0 0.0
Plus: Profit Improvement 41.5 68.1 0.0 0.0
Plus: Goodwill & Intangible Asset Impairments 1,237.8 0.0 1.5 1.5
Plus: Jos. A. Bank Integration 0.0 8.8 0.0 0.0
Plus: Macy's Termination 0.0 0.0 17.2 0.0
Plus: Divestiture of MW Cleaners 0.0 0.0 0.0 3.8
Plus: Closure of Rental Product Distribution Center 0.0 0.0 0.0 4.4
Plus: Other 7.1 19.5 0.0 0.0
Adjusted EBIT $238.5 $229.2 $248.1 $240.5
Plus: Depreciation and amortization 120.4 107.9 106.5 105.6
Adjusted EBITDA $358.9 $337.1 $354.6 $346.1

Note: Added depreciation and amortization to the Company’s adjusted EBIT calculations to arrive at adjusted EBITDA; may not sum due to rounding
Source: Company Filings

October 15, 2018 29

CLICK TO
GAAP toEDIT MASTER TITLE
Non-GAAP STYLE
Reconciliations – Free Cash Flow

($ in millions) 2015 2016 2017 TTM Q2 2018

Free Cash Flow Reconciliation:
Net cash provided by operating activities $131.7 $242.6 $350.8 $408.2
Capex (115.5) (99.7) (95.0) (85.6)

Free Cash Flow Reconciliation: $16.2 $142.9 $255.8 $322.6

Note: Amounts may not sum due to rounding

Source: Company Filings

October 15, 2018 30