GOING FAST
EXTRA 20% OFF*
Save on select styles with code EXTRA20
Shop Now
*Exclusions apply

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

Size 8.5 Medium Size Ankle Leather Products

156 items found

Filters

Search Results

Ariat - Turbo Duratread 6" Waterproof Work Boots. Color Dark Brown. $169.95. 4.3 out of 5 stars

Brown Ariat Turbo Duratread 6" Waterproof Work Boots

Brown Ariat Turbo Duratread 6" Waterproof Work Boots

Brand Name: Ariat
Product Name: Turbo Duratread 6" Waterproof Work Boots
Gender: Men's
Color: Dark Brown
Price: $169.95
Rating: 4Rated 4 stars out of 5(6)

Taft - Lewis. Color Oro Viejo. On sale for $295.00. MSRP $349.00. 15% off.

Brown Taft Lewis

Brown Taft Lewis

Brand Name: Taft
Product Name: Lewis
Gender: Men's
Color: Oro Viejo
Price: $295MSRP: $34915% OFF
Rating

Taft - Glen. Color Black Suede. $348.99.

Black Taft Glen

Black Taft Glen

Brand Name: Taft
Product Name: Glen
Gender: Men's
Color: Black Suede
Price: $348.99
Rating

To Boot New York - Bailey. Color Black 1. Low Stock. $550.00. 5.0 out of 5 stars

Low Stock

Black To Boot New York Bailey

Black To Boot New York Bailey

Brand Name: To Boot New York
Product Name: Bailey
Gender: Men's
Color: Black 1
Price: $550
Rating: 5Rated 5 stars out of 5(2)

Allen Edmonds - Tanner Chelsea Short Boots. Color Black. $550.00.

Black Allen Edmonds Tanner Chelsea Short Boots

Black Allen Edmonds Tanner Chelsea Short Boots

Brand Name: Allen Edmonds
Product Name: Tanner Chelsea Short Boots
Gender: Men's
Color: Black
Price: $550
Rating

Magnanni - Java. Color Indigo. Low Stock. On sale for $440.00. MSRP $550.00. 20% off.

Low Stock

Blue Magnanni Java

Blue Magnanni Java

Brand Name: Magnanni
Product Name: Java
Gender: Men's
Color: Indigo
Price: $440MSRP: $55020% OFF
Rating

Frye - Hudson Workboot Plain Toe. Color Whiskey. On sale for $220.80. MSRP $368.00. 40% off. 4.0 out of 5 stars

Brown Frye Hudson Workboot Plain Toe

Brown Frye Hudson Workboot Plain Toe

+2

Brand Name: Frye
Product Name: Hudson Workboot Plain Toe
Gender: Men's
Color: Whiskey
Price: $220.80MSRP: $36840% OFF
Rating: 4Rated 4 stars out of 5(3)

To Boot New York - Monaco. Color Slate. $425.00.

Gray To Boot New York Monaco

Gray To Boot New York Monaco

+2

Brand Name: To Boot New York
Product Name: Monaco
Gender: Men's
Color: Slate
Price: $425
Rating

To Boot New York - Gilmour. Color Black. Low Stock. $525.00.

Low Stock

Black To Boot New York Gilmour

Black To Boot New York Gilmour

Brand Name: To Boot New York
Product Name: Gilmour
Gender: Men's
Color: Black
Price: $525
Rating

Vince - Jerome. Color Cocoa Brown Leather. On sale for $300.00. MSRP $330.00. 9% off.

Brown Vince Jerome

Brown Vince Jerome

Brand Name: Vince
Product Name: Jerome
Gender: Men's
Color: Cocoa Brown Leather
Price: $300MSRP: $3309% OFF
Rating

Allen Edmonds - Higgins Mill Lace-Up. Color Brown Waxed Suede. On sale for $385.00. MSRP $550.00. 30% off.

Brown Allen Edmonds Higgins Mill Lace-Up

Brown Allen Edmonds Higgins Mill Lace-Up

Brand Name: Allen Edmonds
Product Name: Higgins Mill Lace-Up
Gender: Men's
Color: Brown Waxed Suede
Price: $385MSRP: $55030% OFF
Rating

Taft - Darcey. Color Brown. $295.00.

Brown Taft Darcey

Brown Taft Darcey

Brand Name: Taft
Product Name: Darcey
Gender: Men's
Color: Brown
Price: $295
Rating

Ariat - Longview Shock Shield 8" Waterproof Work Boots. Color Copper Brown. $199.95.

Brown Ariat Longview Shock Shield 8" Waterproof Work Boots

Brown Ariat Longview Shock Shield 8" Waterproof Work Boots

Brand Name: Ariat
Product Name: Longview Shock Shield 8" Waterproof Work Boots
Gender: Men's
Color: Copper Brown
Price: $199.95
Rating

Ariat - Longview Shock Shield 8" Waterproof Composite Toe Work Boots. Color Copper Brown. $209.95. 5.0 out of 5 stars

Brown Ariat Longview Shock Shield 8" Waterproof Composite Toe Work Boots

Brown Ariat Longview Shock Shield 8" Waterproof Composite Toe Work Boots

Brand Name: Ariat
Product Name: Longview Shock Shield 8" Waterproof Composite Toe Work Boots
Gender: Men's
Color: Copper Brown
Price: $209.95
Rating: 5Rated 5 stars out of 5(2)

Taft - Boston. Color Olive. $295.00.

Olive Taft Boston

Olive Taft Boston

+3

Brand Name: Taft
Product Name: Boston
Gender: Men's
Color: Olive
Price: $295
Rating

Mephisto - Clement. Color Dark Brown. $449.00.

Brown Mephisto Clement

Brown Mephisto Clement

Brand Name: Mephisto
Product Name: Clement
Gender: Men's
Color: Dark Brown
Price: $449
Rating

Caterpillar - Threshold Rebound Waterproof Non Metallic Composite Toe. Color Pyramid. $154.95. 4.0 out of 5 stars

Black Caterpillar Threshold Rebound Waterproof Non Metallic Composite Toe

Black Caterpillar Threshold Rebound Waterproof Non Metallic Composite Toe

+3

Brand Name: Caterpillar
Product Name: Threshold Rebound Waterproof Non Metallic Composite Toe
Gender: Men's
Color: Pyramid
Price: $154.95
Rating: 4Rated 4 stars out of 5(17)

Asolo - Nuptse GV. Color Brown 1. $520.00. 2.3 out of 5 stars

Brown Asolo Nuptse GV

Brown Asolo Nuptse GV

Brand Name: Asolo
Product Name: Nuptse GV
Gender: Men's
Color: Brown 1
Price: $520
Rating: 2Rated 2 stars out of 5(3)

To Boot New York - Jonathan. Color Dark Brown. Low Stock. $450.00.

Low Stock

Brown To Boot New York Jonathan

Brown To Boot New York Jonathan

Brand Name: To Boot New York
Product Name: Jonathan
Gender: Men's
Color: Dark Brown
Price: $450
Rating

Allen Edmonds - Durango Zip Short Boots. Color Black. Low Stock. On sale for $416.50. MSRP $595.00. 30% off.

Low Stock

Black Allen Edmonds Durango Zip Short Boots

Black Allen Edmonds Durango Zip Short Boots

+2

Brand Name: Allen Edmonds
Product Name: Durango Zip Short Boots
Gender: Men's
Color: Black
Price: $416.50MSRP: $59530% OFF
Rating

Ariat - Rebar Flex SD Composite Toe Work Boots. Color Distressed Brown/Stone. $209.95. 3.3 out of 5 stars

Brown Ariat Rebar Flex SD Composite Toe Work Boots

Brown Ariat Rebar Flex SD Composite Toe Work Boots

Brand Name: Ariat
Product Name: Rebar Flex SD Composite Toe Work Boots
Gender: Men's
Color: Distressed Brown/Stone
Price: $209.95
Rating: 3Rated 3 stars out of 5(3)

Steve Madden - Millsen. Color Tan. Low Stock. On sale for $91.00. MSRP $130.00. 30% off.

Low Stock

Tan Steve Madden Millsen

Tan Steve Madden Millsen

Brand Name: Steve Madden
Product Name: Millsen
Gender: Men's
Color: Tan
Price: $91MSRP: $13030% OFF
Rating

. Timberland PRO - Tempe 6 Inch Alloy Safety Toe Waterproof Industrial Work Boots. Color Rust Full Grain. On sale for $149.95. MSRP $160.00. 6% off.

Tan Timberland PRO Tempe 6 Inch Alloy Safety Toe Waterproof Industrial Work Boots

Tan Timberland PRO Tempe 6 Inch Alloy Safety Toe Waterproof Industrial Work Boots

Brand Name: Timberland PRO
Product Name: Tempe 6 Inch Alloy Safety Toe Waterproof Industrial Work Boots
Gender: Men's
Color: Rust Full Grain
Price: $149.95MSRP: $1606% OFF
Rating

Cole Haan - Zerogrand Remastered Waterproof Chelsea Boots. Color Dark Coffee/Oxford Tan. On sale for $161.00. MSRP $230.00. 30% off.

Brown Cole Haan Zerogrand Remastered Waterproof Chelsea Boots

Brown Cole Haan Zerogrand Remastered Waterproof Chelsea Boots

Brand Name: Cole Haan
Product Name: Zerogrand Remastered Waterproof Chelsea Boots
Gender: Men's
Color: Dark Coffee/Oxford Tan
Price: $161MSRP: $23030% OFF
Rating

Hoss - Scout ST 6". Color Brown. $109.95. 4.0 out of 5 stars

Brown Hoss Scout ST 6"

Brown Hoss Scout ST 6"

Brand Name: Hoss
Product Name: Scout ST 6"
Gender: Men's
Color: Brown
Price: $109.95
Rating: 4Rated 4 stars out of 5(1)

Eastland 1955 Edition - Allagash Standard. Color Peanut. Low Stock. $145.00. 5.0 out of 5 stars

Low Stock

Brown Eastland 1955 Edition Allagash Standard

Brown Eastland 1955 Edition Allagash Standard

+3

Brand Name: Eastland 1955 Edition
Product Name: Allagash Standard
Gender: Men's
Color: Peanut
Price: $145
Rating: 5Rated 5 stars out of 5(1)

Cole Haan - Roundhill Grand Chukka Boots. Color Woodbury/Dark Natural/Dark Natural. Low Stock. $259.95.

Low Stock

Brown Cole Haan Roundhill Grand Chukka Boots

Brown Cole Haan Roundhill Grand Chukka Boots

+3

Brand Name: Cole Haan
Product Name: Roundhill Grand Chukka Boots
Gender: Men's
Color: Woodbury/Dark Natural/Dark Natural
Price: $259.95
Rating

Steve Madden - Hatford. Color Tan. On sale for $70.00. MSRP $100.00. 30% off.

Tan Steve Madden Hatford

Tan Steve Madden Hatford

+4

Brand Name: Steve Madden
Product Name: Hatford
Gender: Men's
Color: Tan
Price: $70MSRP: $10030% OFF
Rating

Red Wing Heritage - 6" Moc Toe. Color Black Cherry Excalibur. Low Stock. $319.99. 4.5 out of 5 stars

Low Stock

Red Red Wing Heritage 6" Moc Toe

Red Red Wing Heritage 6" Moc Toe

+7

Brand Name: Red Wing Heritage
Product Name: 6" Moc Toe
Gender: Men's
Color: Black Cherry Excalibur
Price: $319.99
Rating: 5Rated 5 stars out of 5(264)

Frye - Paul Chukka. Color Mushroom. Low Stock. On sale for $169.20. MSRP $188.00. 10% off. 4.0 out of 5 stars

Low Stock

Neutral Frye Paul Chukka

Neutral Frye Paul Chukka

+2

Brand Name: Frye
Product Name: Paul Chukka
Gender: Men's
Color: Mushroom
Price: $169.20MSRP: $18810% OFF
Rating: 4Rated 4 stars out of 5(9)

KEEN Utility - Speedworks Work Sneakers (Carbon-Fiber Toe). Color Black/Steel Grey. $145.00. 3.0 out of 5 stars

Black KEEN Utility Speedworks Work Sneakers (Carbon-Fiber Toe)

Black KEEN Utility Speedworks Work Sneakers (Carbon-Fiber Toe)

+2

Brand Name: KEEN Utility
Product Name: Speedworks Work Sneakers (Carbon-Fiber Toe)
Gender: Men's
Color: Black/Steel Grey
Price: $145
Rating: 3Rated 3 stars out of 5(36)

Clarks - Shepton. Color Dark Brown Leather. On sale for $77.00. MSRP $110.00. 30% off. 1.6 out of 5 stars

Brown Clarks Shepton

Brown Clarks Shepton

+6

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Dark Brown Leather
Price: $77MSRP: $11030% OFF
Rating: 2Rated 2 stars out of 5(7)

Allen Edmonds - Tanner. Color Light Brown Suede. $550.00.

Brown Allen Edmonds Tanner

Brown Allen Edmonds Tanner

+3

Brand Name: Allen Edmonds
Product Name: Tanner
Gender: Men's
Color: Light Brown Suede
Price: $550
Rating

Timberland PRO - Morphix 6" Composite Safety Toe Waterproof. Color Black/Orange. On sale for $159.95. MSRP $170.00. 6% off. 4.2 out of 5 stars

Black Timberland PRO Morphix 6" Composite Safety Toe Waterproof

Black Timberland PRO Morphix 6" Composite Safety Toe Waterproof

+3

Brand Name: Timberland PRO
Product Name: Morphix 6" Composite Safety Toe Waterproof
Gender: Men's
Color: Black/Orange
Price: $159.95MSRP: $1706% OFF
Rating: 4Rated 4 stars out of 5(162)

Allen Edmonds - Tompkins. Color Brown Leather. $550.00. 3.5 out of 5 stars

Brown Allen Edmonds Tompkins

Brown Allen Edmonds Tompkins

+2

Brand Name: Allen Edmonds
Product Name: Tompkins
Gender: Men's
Color: Brown Leather
Price: $550
Rating: 4Rated 4 stars out of 5(2)

SOREL - Buxton™ Lace Waterproof. Color Black/Quarry. Low Stock. $150.00. 4.2 out of 5 stars

Low Stock

Black SOREL Buxton™ Lace Waterproof

Black SOREL Buxton™ Lace Waterproof

+3

Brand Name: SOREL
Product Name: Buxton™ Lace Waterproof
Gender: Men's
Color: Black/Quarry
Price: $150
Rating: 4Rated 4 stars out of 5(4)

Cole Haan - American Classics Chelsea Boots. Color Morel Nubuck Waterproof/Black. On sale for $140.00. MSRP $200.00. 30% off. 3.0 out of 5 stars

Taupe Cole Haan American Classics Chelsea Boots

Taupe Cole Haan American Classics Chelsea Boots

+3

Brand Name: Cole Haan
Product Name: American Classics Chelsea Boots
Gender: Men's
Color: Morel Nubuck Waterproof/Black
Price: $140MSRP: $20030% OFF
Rating: 3Rated 3 stars out of 5(1)

L.L.Bean - 8" Bean Boots. Color Brown/Tan Opaque. $149.00. 4.5 out of 5 stars

Brown L.L.Bean 8" Bean Boots

Brown L.L.Bean 8" Bean Boots

+2

Brand Name: L.L.Bean
Product Name: 8" Bean Boots
Gender: Men's
Color: Brown/Tan Opaque
Price: $149
Rating: 4Rated 4 stars out of 5(879)

L.L.Bean - Rubber Moc. Color Field Olive/Bean Boot Brown/Sail Orange. $99.95. 4.0 out of 5 stars

Olive L.L.Bean Rubber Moc

Olive L.L.Bean Rubber Moc

+4

Brand Name: L.L.Bean
Product Name: Rubber Moc
Gender: Men's
Color: Field Olive/Bean Boot Brown/Sail Orange
Price: $99.95
Rating: 4Rated 4 stars out of 5(216)

Johnston & Murphy - Xc+ Parker Chukka. Color Brown Waterproof Full Grain. Low Stock. On sale for $115.61. MSRP $189.00. 39% off.

Low Stock

Red Johnston & Murphy Xc+ Parker Chukka

Red Johnston & Murphy Xc+ Parker Chukka

+2

Brand Name: Johnston & Murphy
Product Name: Xc+ Parker Chukka
Gender: Men's
Color: Brown Waterproof Full Grain
Price: $115.61MSRP: $18939% OFF
Rating

Johnston & Murphy - XC+ Durham Cap Toe Boots. Color Black Waterproof Full Grain. $218.95. 4.0 out of 5 stars

Black Johnston & Murphy XC+ Durham Cap Toe Boots

Black Johnston & Murphy XC+ Durham Cap Toe Boots

+2

Brand Name: Johnston & Murphy
Product Name: XC+ Durham Cap Toe Boots
Gender: Men's
Color: Black Waterproof Full Grain
Price: $218.95
Rating: 4Rated 4 stars out of 5(1)

Clarks - Shepton Easy. Color Beeswax Leather. On sale for $101.50. MSRP $130.00. 22% off. 5.0 out of 5 stars

Brown Clarks Shepton Easy

Brown Clarks Shepton Easy

+2

Brand Name: Clarks
Product Name: Shepton Easy
Gender: Men's
Color: Beeswax Leather
Price: $101.50MSRP: $13022% OFF
Rating: 5Rated 5 stars out of 5(1)

Dunham - Brisco. Color Black Leather. On sale for $122.50. MSRP $159.95. 23% off. 4.0 out of 5 stars

Black Dunham Brisco

Black Dunham Brisco

+2

Brand Name: Dunham
Product Name: Brisco
Gender: Men's
Color: Black Leather
Price: $122.50MSRP: $159.9523% OFF
Rating: 4Rated 4 stars out of 5(1)

Cole Haan - Chamberlin Grand Chelsea Boots. Color Black Nubuck/Black Water Resistant. $150.00.

Black Cole Haan Chamberlin Grand Chelsea Boots

Black Cole Haan Chamberlin Grand Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: Chamberlin Grand Chelsea Boots
Gender: Men's
Color: Black Nubuck/Black Water Resistant
Price: $150
Rating

Sperry - Mini Lug Chukka. Color Other Beige. $150.00.

Pink Sperry Mini Lug Chukka

Pink Sperry Mini Lug Chukka

+2

Brand Name: Sperry
Product Name: Mini Lug Chukka
Gender: Men's
Color: Other Beige
Price: $150
Rating

Johnston & Murphy - Barrett Plain Toe Boots. Color Tan Full Grain 1. On sale for $179.10. MSRP $199.00. 10% off. 4.5 out of 5 stars

Brown Johnston & Murphy Barrett Plain Toe Boots

Brown Johnston & Murphy Barrett Plain Toe Boots

Brand Name: Johnston & Murphy
Product Name: Barrett Plain Toe Boots
Gender: Men's
Color: Tan Full Grain 1
Price: $179.10MSRP: $19910% OFF
Rating: 5Rated 5 stars out of 5(131)

Johnston & Murphy - Calder Chelsea Boots. Color Brown Oiled Full Grain. $178.95. 5.0 out of 5 stars

Brown Johnston & Murphy Calder Chelsea Boots

Brown Johnston & Murphy Calder Chelsea Boots

Brand Name: Johnston & Murphy
Product Name: Calder Chelsea Boots
Gender: Men's
Color: Brown Oiled Full Grain
Price: $178.95
Rating: 5Rated 5 stars out of 5(1)

Red Wing Heritage - Blacksmith. Color Copper Rough & Tough. $329.99. 4.5 out of 5 stars

Tan Red Wing Heritage Blacksmith

Tan Red Wing Heritage Blacksmith

+2

Brand Name: Red Wing Heritage
Product Name: Blacksmith
Gender: Men's
Color: Copper Rough & Tough
Price: $329.99
Rating: 5Rated 5 stars out of 5(24)

Cole Haan - Judson Grand Chelsea Boots. Color Black Waterproof/Black/Black. $259.95.

Black Cole Haan Judson Grand Chelsea Boots

Black Cole Haan Judson Grand Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: Judson Grand Chelsea Boots
Gender: Men's
Color: Black Waterproof/Black/Black
Price: $259.95
Rating

Eastland 1955 Edition - Chimney Pond. Color Black. On sale for $87.00. MSRP $145.00. 40% off. 5.0 out of 5 stars

Black Eastland 1955 Edition Chimney Pond

Black Eastland 1955 Edition Chimney Pond

+2

Brand Name: Eastland 1955 Edition
Product Name: Chimney Pond
Gender: Men's
Color: Black
Price: $87MSRP: $14540% OFF
Rating: 5Rated 5 stars out of 5(2)

Johnston & Murphy - Upton Chelsea Boots. Color Tan Full Grain. On sale for $119.99. MSRP $179.00. 33% off. 2.0 out of 5 stars

Tan Johnston & Murphy Upton Chelsea Boots

Tan Johnston & Murphy Upton Chelsea Boots

+2

Brand Name: Johnston & Murphy
Product Name: Upton Chelsea Boots
Gender: Men's
Color: Tan Full Grain
Price: $119.99MSRP: $17933% OFF
Rating: 2Rated 2 stars out of 5(1)

Clarks - Desert Boots. Color Brown Suede. On sale for $139.04. MSRP $140.00. 1% off. 4.0 out of 5 stars

Brown Clarks Desert Boots

Brown Clarks Desert Boots

+2

Brand Name: Clarks
Product Name: Desert Boots
Gender: Men's
Color: Brown Suede
Price: $139.04MSRP: $1401% OFF
Rating: 4Rated 4 stars out of 5(1)

Tommy Hilfiger - Berton. Color Cognac. On sale for $59.50. MSRP $119.00. 50% off.

Tan Tommy Hilfiger Berton

Tan Tommy Hilfiger Berton

+2

Brand Name: Tommy Hilfiger
Product Name: Berton
Gender: Men's
Color: Cognac
Price: $59.50MSRP: $11950% OFF
Rating

Stacy Adams - Bradley Chelsea Boot. Color Black. On sale for $119.90. MSRP $160.00. 25% off. 4.2 out of 5 stars

Black Stacy Adams Bradley Chelsea Boot

Black Stacy Adams Bradley Chelsea Boot

+2

Brand Name: Stacy Adams
Product Name: Bradley Chelsea Boot
Gender: Men's
Color: Black
Price: $119.90MSRP: $16025% OFF
Rating: 4Rated 4 stars out of 5(5)

Rockport - Ezra Waterproof Boots. Color Dark Brown Leather. $159.95. 2.8 out of 5 stars

Brown Rockport Ezra Waterproof Boots

Brown Rockport Ezra Waterproof Boots

Brand Name: Rockport
Product Name: Ezra Waterproof Boots
Gender: Men's
Color: Dark Brown Leather
Price: $159.95
Rating: 3Rated 3 stars out of 5(6)

Allen Edmonds - Park Boot. Color Chili. Low Stock. On sale for $385.00. MSRP $550.00. 30% off. 3.9 out of 5 stars

Low Stock

Brown Allen Edmonds Park Boot

Brown Allen Edmonds Park Boot

+2

Brand Name: Allen Edmonds
Product Name: Park Boot
Gender: Men's
Color: Chili
Price: $385MSRP: $55030% OFF
Rating: 4Rated 4 stars out of 5(15)

2 of 2

Join Our Email List

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

*One code per email address.