EXTRA 20% OFF*
*Offer ends 12/29/25 at 11:59pm PST. Exclusions apply.
Hurry, hurry: use code SAVE20
Select styles only.
Shop Now

Skip to search results Skip to filters Skip to sort Skip to selected filters

Size 8.5 Ankle Tan On Sale Products

43 items found

Filters

Search Results

Kenneth Cole - Wilhem. Color Light Brown. On sale for $123.75. MSRP $164.95. 25% off.

Tan Kenneth Cole Wilhem

Tan Kenneth Cole Wilhem

+2

Brand Name: Kenneth Cole
Product Name: Wilhem
Gender: Men's
Color: Light Brown
Price: $123.75MSRP: $164.9525% OFF
Rating

Nunn Bush - Otis 2.0 Chelsea Fashion Leather Boots. Color Tan. On sale for $84.99. MSRP $120.00. 29% off. 4.2 out of 5 stars

Tan Nunn Bush Otis 2.0 Chelsea Fashion Leather Boots

Tan Nunn Bush Otis 2.0 Chelsea Fashion Leather Boots

+3

Brand Name: Nunn Bush
Product Name: Otis 2.0 Chelsea Fashion Leather Boots
Gender: Men's
Color: Tan
Price: $84.99MSRP: $12029% OFF
Rating: 4Rated 4 stars out of 5(8)

Timberland PRO - Direct Attach 6" Steel Toe. Color Wheat-2024 NEW. On sale for $159.95. MSRP $180.00. 11% off. 4.4 out of 5 stars

Tan Timberland PRO Direct Attach 6" Steel Toe

Tan Timberland PRO Direct Attach 6" Steel Toe

Brand Name: Timberland PRO
Product Name: Direct Attach 6" Steel Toe
Gender: Men's
Color: Wheat-2024 NEW
Price: $159.95MSRP: $18011% OFF
Rating: 4Rated 4 stars out of 5(1456)

Steve Madden - Merrnie. Color Tan. On sale for $67.99. MSRP $79.99. 15% off.

Tan Steve Madden Merrnie

Tan Steve Madden Merrnie

+2

Brand Name: Steve Madden
Product Name: Merrnie
Gender: Men's
Color: Tan
Price: $67.99MSRP: $79.9915% OFF
Rating

SOREL - Slabtown 62' Six Waterproof. Color Canoe/Bleached Ceramic. On sale for $111.10. MSRP $175.00. 37% off.

Tan SOREL Slabtown 62' Six Waterproof

Tan SOREL Slabtown 62' Six Waterproof

+2

Brand Name: SOREL
Product Name: Slabtown 62' Six Waterproof
Gender: Men's
Color: Canoe/Bleached Ceramic
Price: $111.10MSRP: $17537% OFF
Rating

Stacy Adams - Platt Chelsea Boots. Color Cognac. On sale for $88.00. MSRP $110.00. 20% off.

Tan Stacy Adams Platt Chelsea Boots

Tan Stacy Adams Platt Chelsea Boots

+2

Brand Name: Stacy Adams
Product Name: Platt Chelsea Boots
Gender: Men's
Color: Cognac
Price: $88MSRP: $11020% OFF
Rating

Johnston & Murphy - Upton Chukka Boots. Color Tan Full Grain. On sale for $109.85. MSRP $169.00. 35% off. 4.7 out of 5 stars

Tan Johnston & Murphy Upton Chukka Boots

Tan Johnston & Murphy Upton Chukka Boots

Brand Name: Johnston & Murphy
Product Name: Upton Chukka Boots
Gender: Men's
Color: Tan Full Grain
Price: $109.85MSRP: $16935% OFF
Rating: 5Rated 5 stars out of 5(173)

Nunn Bush - Excavate Plain Toe Chukka Boots. Color Tan. On sale for $64.95. MSRP $95.00. 32% off. 4.4 out of 5 stars

Tan Nunn Bush Excavate Plain Toe Chukka Boots

Tan Nunn Bush Excavate Plain Toe Chukka Boots

+1

Brand Name: Nunn Bush
Product Name: Excavate Plain Toe Chukka Boots
Gender: Men's
Color: Tan
Price: $64.95MSRP: $9532% OFF
Rating: 4Rated 4 stars out of 5(24)

Polo Ralph Lauren - Asher Leather Chelsea Boots. Color Tan. On sale for $175.28. MSRP $198.00. 11% off. 3.0 out of 5 stars

Tan Polo Ralph Lauren Asher Leather Chelsea Boots

Tan Polo Ralph Lauren Asher Leather Chelsea Boots

+2

Brand Name: Polo Ralph Lauren
Product Name: Asher Leather Chelsea Boots
Gender: Men's
Color: Tan
Price: $175.28MSRP: $19811% OFF
Rating: 3Rated 3 stars out of 5(1)

Florsheim - Launch Plain Toe Chukka Boots. Color Cognac Multi. On sale for $121.50. MSRP $135.00. 10% off.

Tan Florsheim Launch Plain Toe Chukka Boots

Tan Florsheim Launch Plain Toe Chukka Boots

Brand Name: Florsheim
Product Name: Launch Plain Toe Chukka Boots
Gender: Men's
Color: Cognac Multi
Price: $121.50MSRP: $13510% OFF
Rating

Sperry - Stringer. Color Tan. On sale for $117.00. MSRP $130.00. 10% off.

Tan Sperry Stringer

Tan Sperry Stringer

Brand Name: Sperry
Product Name: Stringer
Gender: Men's
Color: Tan
Price: $117MSRP: $13010% OFF
Rating

Johnston & Murphy - Connelly Plain Toe Boots. Color Tan Full Grain. Low Stock. On sale for $149.99. MSRP $219.00. 32% off. 4.2 out of 5 stars

Low Stock

Tan Johnston & Murphy Connelly Plain Toe Boots

Tan Johnston & Murphy Connelly Plain Toe Boots

Brand Name: Johnston & Murphy
Product Name: Connelly Plain Toe Boots
Gender: Men's
Color: Tan Full Grain
Price: $149.99MSRP: $21932% OFF
Rating: 4Rated 4 stars out of 5(60)

Tommy Hilfiger - Oregon. Color Cognac. On sale for $35.98. MSRP $89.95. 60% off.

Tan Tommy Hilfiger Oregon

Tan Tommy Hilfiger Oregon

Brand Name: Tommy Hilfiger
Product Name: Oregon
Gender: Men's
Color: Cognac
Price: $35.98MSRP: $89.9560% OFF
Rating

Frye - Astor Chukka. Color Tan. Low Stock. On sale for $129.98. MSRP $178.00. 27% off. 4.0 out of 5 stars

Low Stock

Tan Frye Astor Chukka

Tan Frye Astor Chukka

Brand Name: Frye
Product Name: Astor Chukka
Gender: Men's
Color: Tan
Price: $129.98MSRP: $17827% OFF
Rating: 4Rated 4 stars out of 5(23)

Nunn Bush - Ozark 2.0 Plain Toe Chukka Leather Boots. Color Tan. On sale for $84.99. MSRP $120.00. 29% off. 4.2 out of 5 stars

Tan Nunn Bush Ozark 2.0 Plain Toe Chukka Leather Boots

Tan Nunn Bush Ozark 2.0 Plain Toe Chukka Leather Boots

+3

Brand Name: Nunn Bush
Product Name: Ozark 2.0 Plain Toe Chukka Leather Boots
Gender: Men's
Color: Tan
Price: $84.99MSRP: $12029% OFF
Rating: 4Rated 4 stars out of 5(11)

Steve Madden - Millsen. Color Tan. Low Stock. On sale for $104.00. MSRP $130.00. 20% off.

Low Stock

Tan Steve Madden Millsen

Tan Steve Madden Millsen

Brand Name: Steve Madden
Product Name: Millsen
Gender: Men's
Color: Tan
Price: $104MSRP: $13020% OFF
Rating

Stacy Adams - Gabriel Chelsea Boot. Color Sand Suede. Low Stock. On sale for $94.95. MSRP $130.00. 27% off. 4.2 out of 5 stars

Low Stock

Tan Stacy Adams Gabriel Chelsea Boot

Tan Stacy Adams Gabriel Chelsea Boot

Brand Name: Stacy Adams
Product Name: Gabriel Chelsea Boot
Gender: Men's
Color: Sand Suede
Price: $94.95MSRP: $13027% OFF
Rating: 4Rated 4 stars out of 5(19)

Frye - Barrett Lace Up. Color Cognac. On sale for $173.60. MSRP $248.00. 30% off. 5.0 out of 5 stars

Tan Frye Barrett Lace Up

Tan Frye Barrett Lace Up

+3

Brand Name: Frye
Product Name: Barrett Lace Up
Gender: Men's
Color: Cognac
Price: $173.60MSRP: $24830% OFF
Rating: 5Rated 5 stars out of 5(2)

Nunn Bush - Circuit DC Plain Toe Chukka. Color Cognac. On sale for $59.95. MSRP $90.00. 33% off. 3.8 out of 5 stars

Tan Nunn Bush Circuit DC Plain Toe Chukka

Tan Nunn Bush Circuit DC Plain Toe Chukka

+3

Brand Name: Nunn Bush
Product Name: Circuit DC Plain Toe Chukka
Gender: Men's
Color: Cognac
Price: $59.95MSRP: $9033% OFF
Rating: 4Rated 4 stars out of 5(52)

Cole Haan - American Classics Plain Toe Boot Waterproof. Color Morel Suede/Golden Honey/Waterproof. On sale for $178.50. MSRP $210.00. 15% off. 4.4 out of 5 stars

Tan Cole Haan American Classics Plain Toe Boot Waterproof

Tan Cole Haan American Classics Plain Toe Boot Waterproof

+2

Brand Name: Cole Haan
Product Name: American Classics Plain Toe Boot Waterproof
Gender: Men's
Color: Morel Suede/Golden Honey/Waterproof
Price: $178.50MSRP: $21015% OFF
Rating: 4Rated 4 stars out of 5(140)

Nunn Bush - Karnak Plain Toe Boots Chukka. Color Tan. On sale for $84.99. MSRP $120.00. 29% off. 4.6 out of 5 stars

Tan Nunn Bush Karnak Plain Toe Boots Chukka

Tan Nunn Bush Karnak Plain Toe Boots Chukka

+1

Brand Name: Nunn Bush
Product Name: Karnak Plain Toe Boots Chukka
Gender: Men's
Color: Tan
Price: $84.99MSRP: $12029% OFF
Rating: 5Rated 5 stars out of 5(19)

Stacy Adams - Madison Cap Toe Lace-Up Boots. Color Cognac. On sale for $131.25. MSRP $175.00. 25% off. 5.0 out of 5 stars

Tan Stacy Adams Madison Cap Toe Lace-Up Boots

Tan Stacy Adams Madison Cap Toe Lace-Up Boots

+4

Brand Name: Stacy Adams
Product Name: Madison Cap Toe Lace-Up Boots
Gender: Men's
Color: Cognac
Price: $131.25MSRP: $17525% OFF
Rating: 5Rated 5 stars out of 5(1)

Dockers - Weston. Color Cognac. On sale for $69.99. MSRP $95.00. 26% off.

Tan Dockers Weston

Tan Dockers Weston

+3

Brand Name: Dockers
Product Name: Weston
Gender: Men's
Color: Cognac
Price: $69.99MSRP: $9526% OFF
Rating

Dockers - Esmond. Color Tan. On sale for $85.50. MSRP $95.00. 10% off. 3.5 out of 5 stars

Tan Dockers Esmond

Tan Dockers Esmond

+5

Brand Name: Dockers
Product Name: Esmond
Gender: Men's
Color: Tan
Price: $85.50MSRP: $9510% OFF
Rating: 4Rated 4 stars out of 5(2)

. Timberland PRO - Sawhorse 6" Composite Safety Toe. Color Wheat 1. On sale for $129.95. MSRP $150.00. 13% off. 3.4 out of 5 stars

Tan Timberland PRO Sawhorse 6" Composite Safety Toe

Tan Timberland PRO Sawhorse 6" Composite Safety Toe

+6

Brand Name: Timberland PRO
Product Name: Sawhorse 6" Composite Safety Toe
Gender: Unisex
Color: Wheat 1
Price: $129.95MSRP: $15013% OFF
Rating: 3Rated 3 stars out of 5(1440)

Nunn Bush - Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka. Color Tan. On sale for $89.95. MSRP $120.00. 25% off. 5.0 out of 5 stars

Tan Nunn Bush Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka

Tan Nunn Bush Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka

+2

Brand Name: Nunn Bush
Product Name: Karnak Plain Toe Chelsea Boots Lightweight Comfortable Chukka
Gender: Men's
Color: Tan
Price: $89.95MSRP: $12025% OFF
Rating: 5Rated 5 stars out of 5(2)

. Marc Joseph New York - Hudson Yards 2.0 (Hands Free Technology). Color Cognac Faux Leather. On sale for $79.95. MSRP $195.00. 59% off. 5.0 out of 5 stars

Tan Marc Joseph New York Hudson Yards 2.0 (Hands Free Technology)

Tan Marc Joseph New York Hudson Yards 2.0 (Hands Free Technology)

+4

Brand Name: Marc Joseph New York
Product Name: Hudson Yards 2.0 (Hands Free Technology)
Gender: Men's
Color: Cognac Faux Leather
Price: $79.95MSRP: $19559% OFF
Rating: 5Rated 5 stars out of 5(2)

Nunn Bush - Odell 2.0 Wingtip Dress Casual Chukka Leather Boots. Color Tan. On sale for $84.99. MSRP $120.00. 29% off. 4.6 out of 5 stars

Tan Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boots

Tan Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boots

+1

Brand Name: Nunn Bush
Product Name: Odell 2.0 Wingtip Dress Casual Chukka Leather Boots
Gender: Men's
Color: Tan
Price: $84.99MSRP: $12029% OFF
Rating: 5Rated 5 stars out of 5(11)

Rockport - Storm Surge Water Proof Plain Toe Boots. Color Tan. On sale for $99.95. MSRP $159.95. 38% off. 3.4 out of 5 stars

Tan Rockport Storm Surge Water Proof Plain Toe Boots

Tan Rockport Storm Surge Water Proof Plain Toe Boots

+2

Brand Name: Rockport
Product Name: Storm Surge Water Proof Plain Toe Boots
Gender: Men's
Color: Tan
Price: $99.95MSRP: $159.9538% OFF
Rating: 3Rated 3 stars out of 5(17)

Johnston & Murphy - Upton Chukka. Color Tan Oiled Full Grain. On sale for $119.99. MSRP $179.00. 33% off. 4.1 out of 5 stars

Tan Johnston & Murphy Upton Chukka

Tan Johnston & Murphy Upton Chukka

+4

Brand Name: Johnston & Murphy
Product Name: Upton Chukka
Gender: Men's
Color: Tan Oiled Full Grain
Price: $119.99MSRP: $17933% OFF
Rating: 4Rated 4 stars out of 5(265)

Stacy Adams - Eastmont Elastic Lace Boots. Color Cognac. Low Stock. On sale for $42.00. MSRP $140.00. 70% off.

Low Stock

Tan Stacy Adams Eastmont Elastic Lace Boots

Tan Stacy Adams Eastmont Elastic Lace Boots

+3

Brand Name: Stacy Adams
Product Name: Eastmont Elastic Lace Boots
Gender: Men's
Color: Cognac
Price: $42MSRP: $14070% OFF
Rating

Nunn Bush - Chase Plain Toe Chukka Contemporary Fashion Boot. Color Cognac. On sale for $64.95. MSRP $95.00. 32% off. 4.1 out of 5 stars

Tan Nunn Bush Chase Plain Toe Chukka Contemporary Fashion Boot

Tan Nunn Bush Chase Plain Toe Chukka Contemporary Fashion Boot

+3

Brand Name: Nunn Bush
Product Name: Chase Plain Toe Chukka Contemporary Fashion Boot
Gender: Men's
Color: Cognac
Price: $64.95MSRP: $9532% OFF
Rating: 4Rated 4 stars out of 5(16)

Frye - Tyler Flex Chelsea. Color Cognac. On sale for $187.60. MSRP $268.00. 30% off. 3.5 out of 5 stars

Tan Frye Tyler Flex Chelsea

Tan Frye Tyler Flex Chelsea

+4

Brand Name: Frye
Product Name: Tyler Flex Chelsea
Gender: Men's
Color: Cognac
Price: $187.60MSRP: $26830% OFF
Rating: 4Rated 4 stars out of 5(6)

Tommy Hilfiger - Bage. Color Cognac Tumble. On sale for $83.30. MSRP $119.00. 30% off. 4.5 out of 5 stars

Tan Tommy Hilfiger Bage

Tan Tommy Hilfiger Bage

+4

Brand Name: Tommy Hilfiger
Product Name: Bage
Gender: Men's
Color: Cognac Tumble
Price: $83.30MSRP: $11930% OFF
Rating: 5Rated 5 stars out of 5(2)

Steve Madden - Hatford. Color Tan. On sale for $75.03. MSRP $100.00. 25% off.

Tan Steve Madden Hatford

Tan Steve Madden Hatford

+4

Brand Name: Steve Madden
Product Name: Hatford
Gender: Men's
Color: Tan
Price: $75.03MSRP: $10025% OFF
Rating

Nunn Bush - Karnak Moc Toe Boots Lightweight Comfortable Chukka. Color Tan. On sale for $84.99. MSRP $120.00. 29% off. 4.3 out of 5 stars

Tan Nunn Bush Karnak Moc Toe Boots Lightweight Comfortable Chukka

Tan Nunn Bush Karnak Moc Toe Boots Lightweight Comfortable Chukka

+1

Brand Name: Nunn Bush
Product Name: Karnak Moc Toe Boots Lightweight Comfortable Chukka
Gender: Men's
Color: Tan
Price: $84.99MSRP: $12029% OFF
Rating: 4Rated 4 stars out of 5(11)

ECCO - Metropole Milan Chukka Boots. Color Camel Suede. On sale for $140.35. MSRP $194.95. 28% off. 4.0 out of 5 stars

Tan ECCO Metropole Milan Chukka Boots

Tan ECCO Metropole Milan Chukka Boots

+2

Brand Name: ECCO
Product Name: Metropole Milan Chukka Boots
Gender: Men's
Color: Camel Suede
Price: $140.35MSRP: $194.9528% OFF
Rating: 4Rated 4 stars out of 5(1)

Florsheim - Rucci Wingtip Lace Boots. Color Cognac. On sale for $139.15. MSRP $155.00. 10% off. 5.0 out of 5 stars

Tan Florsheim Rucci Wingtip Lace Boots

Tan Florsheim Rucci Wingtip Lace Boots

+2

Brand Name: Florsheim
Product Name: Rucci Wingtip Lace Boots
Gender: Men's
Color: Cognac
Price: $139.15MSRP: $15510% OFF
Rating: 5Rated 5 stars out of 5(25)

Johnston & Murphy - Connelly Wing Tip Boot. Color Tan Full Grain. On sale for $149.99. MSRP $219.00. 32% off. 3.2 out of 5 stars

Tan Johnston & Murphy Connelly Wing Tip Boot

Tan Johnston & Murphy Connelly Wing Tip Boot

Brand Name: Johnston & Murphy
Product Name: Connelly Wing Tip Boot
Gender: Men's
Color: Tan Full Grain
Price: $149.99MSRP: $21932% OFF
Rating: 3Rated 3 stars out of 5(58)

Tommy Hilfiger - Berton. Color Cognac. On sale for $83.30. MSRP $119.00. 30% off.

Tan Tommy Hilfiger Berton

Tan Tommy Hilfiger Berton

+2

Brand Name: Tommy Hilfiger
Product Name: Berton
Gender: Men's
Color: Cognac
Price: $83.30MSRP: $11930% OFF
Rating

Rockport - Rugged Bucks Waterproof Boot. Color Tan. On sale for $144.95. MSRP $169.95. 15% off. 3.9 out of 5 stars

Tan Rockport Rugged Bucks Waterproof Boot

Tan Rockport Rugged Bucks Waterproof Boot

Brand Name: Rockport
Product Name: Rugged Bucks Waterproof Boot
Gender: Men's
Color: Tan
Price: $144.95MSRP: $169.9515% OFF
Rating: 4Rated 4 stars out of 5(177)

Tommy Hilfiger - Tarlin. Color Cognac. On sale for $67.72. MSRP $119.00. 43% off.

Tan Tommy Hilfiger Tarlin

Tan Tommy Hilfiger Tarlin

Brand Name: Tommy Hilfiger
Product Name: Tarlin
Gender: Men's
Color: Cognac
Price: $67.72MSRP: $11943% OFF
Rating

Cole Haan - Zerogrand Remastered Hiking Boots Water Proof. Color Woodbury/Madeira/Birch. Low Stock. On sale for $169.95. MSRP $250.00. 32% off. 4.0 out of 5 stars

Low Stock

Tan Cole Haan Zerogrand Remastered Hiking Boots Water Proof

Tan Cole Haan Zerogrand Remastered Hiking Boots Water Proof

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Hiking Boots Water Proof
Gender: Men's
Color: Woodbury/Madeira/Birch
Price: $169.95MSRP: $25032% OFF
Rating: 4Rated 4 stars out of 5(3)

Join Our Email List

Never miss out on latest drops & sales—plus, new subscribers get 10% off.*

*One code per email address.