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

Size 7.5 Ankle Leather Comfort Products

35 items found

Sort By

Your Selections

Search Results

Frye - The Safety-Crafted Wellington Work Boots. Color Dark Brown. On sale for $179.95. MSRP $206.00. 13% off.

Brown Frye The Safety-Crafted Wellington Work Boots

Brown Frye The Safety-Crafted Wellington Work Boots

Brand Name: Frye
Product Name: The Safety-Crafted Wellington Work Boots
Gender: Men's
Color: Dark Brown
Price: $179.95MSRP: $206.0013% OFF
Rating

Nunn Bush - Odell Wingtip Boot with KORE Walking Comfort Technology. Color Brown CH. On sale for $97.75. MSRP $115.00. 15% off. 4.2 out of 5 stars

Brown Nunn Bush Odell Wingtip Boot with KORE Walking Comfort Technology

Brown Nunn Bush Odell Wingtip Boot with KORE Walking Comfort Technology

+3

Brand Name: Nunn Bush
Product Name: Odell Wingtip Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Brown CH
Price: $97.75MSRP: $115.0015% OFF
Rating: 4Rated 4 stars out of 5(128)

Dansko - Lizanne. Color Black Oiled Pull Up. On sale for $129.46. MSRP $184.95. 30% off. 3.5 out of 5 stars

Black Dansko Lizanne

Black Dansko Lizanne

+2

Brand Name: Dansko
Product Name: Lizanne
Gender: Women's
Color: Black Oiled Pull Up
Price: $129.46MSRP: $184.9530% OFF
Rating: 4Rated 4 stars out of 5(15)

Nunn Bush - Odell 2.0 Wingtip Dress Casual Chukka Leather Boot. Color Brown. On sale for $79.95. MSRP $109.95. 27% off. 4.5 out of 5 stars

Brown Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boot

Brown Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boot

+1

Brand Name: Nunn Bush
Product Name: Odell 2.0 Wingtip Dress Casual Chukka Leather Boot
Gender: Men's
Color: Brown
Price: $79.95MSRP: $109.9527% OFF
Rating: 5Rated 5 stars out of 5(8)

Dockers - Esmond. Color Cognac. On sale for $59.50. MSRP $85.00. 30% off.

Tan Dockers Esmond

Tan Dockers Esmond

+4

Brand Name: Dockers
Product Name: Esmond
Gender: Men's
Color: Cognac
Price: $59.50MSRP: $85.0030% OFF
Rating

Florsheim - Duke. Color Black Cavello. On sale for $140.71. MSRP $150.00. 6% off. 4.5 out of 5 stars

Black Florsheim Duke

Black Florsheim Duke

+2

Brand Name: Florsheim
Product Name: Duke
Gender: Men's
Color: Black Cavello
Price: $140.71MSRP: $150.006% OFF
Rating: 5Rated 5 stars out of 5(939)

ECCO Sport - Ultra Terrain Waterproof Mid Hiking. Color Mocha/Mocha/Black. On sale for $191.63. MSRP $225.00. 15% off.

Black ECCO Sport Ultra Terrain Waterproof Mid Hiking

Black ECCO Sport Ultra Terrain Waterproof Mid Hiking

Brand Name: ECCO Sport
Product Name: Ultra Terrain Waterproof Mid Hiking
Gender: Men's
Color: Mocha/Mocha/Black
Price: $191.63MSRP: $225.0015% OFF
Rating

Nunn Bush - Otis 2.0 Chelsea Fashion Leather Boot. Color Brown. On sale for $79.95. MSRP $109.95. 27% off. 4.2 out of 5 stars

Brown Nunn Bush Otis 2.0 Chelsea Fashion Leather Boot

Brown Nunn Bush Otis 2.0 Chelsea Fashion Leather Boot

+3

Brand Name: Nunn Bush
Product Name: Otis 2.0 Chelsea Fashion Leather Boot
Gender: Men's
Color: Brown
Price: $79.95MSRP: $109.9527% OFF
Rating: 4Rated 4 stars out of 5(6)

Allen Edmonds - Higginsfplug. Color Black. Low Stock. On sale for $346.50. MSRP $495.00. 30% off. 4.3 out of 5 stars

Low Stock

Black Allen Edmonds Higginsfplug

Black Allen Edmonds Higginsfplug

+3

Brand Name: Allen Edmonds
Product Name: Higginsfplug
Gender: Men's
Color: Black
Price: $346.50MSRP: $495.0030% OFF
Rating: 4Rated 4 stars out of 5(13)

Florsheim - Rucci Plain Toe Chukka Boot. Color Black Smooth. On sale for $119.99. MSRP $140.00. 14% off. 4.3 out of 5 stars

Black Florsheim Rucci Plain Toe Chukka Boot

Black Florsheim Rucci Plain Toe Chukka Boot

Brand Name: Florsheim
Product Name: Rucci Plain Toe Chukka Boot
Gender: Men's
Color: Black Smooth
Price: $119.99MSRP: $140.0014% OFF
Rating: 4Rated 4 stars out of 5(44)

Tommy Hilfiger - Bage. Color Dark Brown. On sale for $65.40. MSRP $109.00. 40% off. 5.0 out of 5 stars

Brown Tommy Hilfiger Bage

Brown Tommy Hilfiger Bage

+3

Brand Name: Tommy Hilfiger
Product Name: Bage
Gender: Men's
Color: Dark Brown
Price: $65.40MSRP: $109.0040% OFF
Rating: 5Rated 5 stars out of 5(1)

Clarks - Shepton. Color Taupe Distressed Leather. On sale for $79.96. MSRP $100.00. 20% off. 2.0 out of 5 stars

Taupe Clarks Shepton

Taupe Clarks Shepton

+5

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Taupe Distressed Leather
Price: $79.96MSRP: $100.0020% OFF
Rating: 2Rated 2 stars out of 5(4)

Vans - U MTE™ Crestline Waterproof. Color Teak. Low Stock. On sale for $143.95. MSRP $160.00. 10% off. 5.0 out of 5 stars

Low Stock

Brown Vans U MTE™ Crestline Waterproof

Brown Vans U MTE™ Crestline Waterproof

+7

Brand Name: Vans
Product Name: U MTE™ Crestline Waterproof
Gender: Unisex
Color: Teak
Price: $143.95MSRP: $160.0010% OFF
Rating: 5Rated 5 stars out of 5(1)

Clarks - Shepton Easy. Color Black Leather. On sale for $100.75. MSRP $120.00. 16% off.

Black Clarks Shepton Easy

Black Clarks Shepton Easy

+2

Brand Name: Clarks
Product Name: Shepton Easy
Gender: Men's
Color: Black Leather
Price: $100.75MSRP: $120.0016% OFF
Rating

L.L.Bean - Trailfinder Waterproof Hiker Mid. Color Carbon Navy. On sale for $139.00. MSRP $169.00. 18% off. 4.8 out of 5 stars

Navy L.L.Bean Trailfinder Waterproof Hiker Mid

Navy L.L.Bean Trailfinder Waterproof Hiker Mid

+2

Brand Name: L.L.Bean
Product Name: Trailfinder Waterproof Hiker Mid
Gender: Men's
Color: Carbon Navy
Price: $139.00MSRP: $169.0018% OFF
Rating: 5Rated 5 stars out of 5(5)

Florsheim - Rucci Plain Toe Chukka. Color Cognac. On sale for $119.00. MSRP $140.00. 15% off. 5.0 out of 5 stars

Tan Florsheim Rucci Plain Toe Chukka

Tan Florsheim Rucci Plain Toe Chukka

Brand Name: Florsheim
Product Name: Rucci Plain Toe Chukka
Gender: Men's
Color: Cognac
Price: $119.00MSRP: $140.0015% OFF
Rating: 5Rated 5 stars out of 5(10)

Stacy Adams - Henry Cap Toe Lace-Up Boot. Color Black. Low Stock. On sale for $127.50. MSRP $150.00. 15% off. 5.0 out of 5 stars

Low Stock

Black Stacy Adams Henry Cap Toe Lace-Up Boot

Black Stacy Adams Henry Cap Toe Lace-Up Boot

Brand Name: Stacy Adams
Product Name: Henry Cap Toe Lace-Up Boot
Gender: Men's
Color: Black
Price: $127.50MSRP: $150.0015% OFF
Rating: 5Rated 5 stars out of 5(2)

Red Wing Heritage - Classic Chelsea. Color Black Harness. On sale for $299.99. MSRP $329.99. 9% off. 4.8 out of 5 stars

Black Red Wing Heritage Classic Chelsea

Black Red Wing Heritage Classic Chelsea

+3

Brand Name: Red Wing Heritage
Product Name: Classic Chelsea
Gender: Men's
Color: Black Harness
Price: $299.99MSRP: $329.999% OFF
Rating: 5Rated 5 stars out of 5(13)

Rockport - Flynn. Color Black Leather. On sale for $149.95. MSRP $159.95. 6% off. 2.8 out of 5 stars

Black Rockport Flynn

Black Rockport Flynn

+2

Brand Name: Rockport
Product Name: Flynn
Gender: Men's
Color: Black Leather
Price: $149.95MSRP: $159.956% OFF
Rating: 3Rated 3 stars out of 5(4)

Florsheim - Rucci Wingtip Lace Boot. Color Black. On sale for $136.89. MSRP $140.00. 2% off. 5.0 out of 5 stars

Black Florsheim Rucci Wingtip Lace Boot

Black Florsheim Rucci Wingtip Lace Boot

+2

Brand Name: Florsheim
Product Name: Rucci Wingtip Lace Boot
Gender: Men's
Color: Black
Price: $136.89MSRP: $140.002% OFF
Rating: 5Rated 5 stars out of 5(7)

Clarks - Wallabee Boot. Color Black Leather. Low Stock. On sale for $160.00. MSRP $170.00. 6% off. 4.5 out of 5 stars

Low Stock

Black Clarks Wallabee Boot

Black Clarks Wallabee Boot

+4

Brand Name: Clarks
Product Name: Wallabee Boot
Gender: Men's
Color: Black Leather
Price: $160.00MSRP: $170.006% OFF
Rating: 4Rated 4 stars out of 5(59)

Steve Madden - Noby. Color Brown Leather. On sale for $87.00. MSRP $150.00. 42% off. 4.0 out of 5 stars

Brown Steve Madden Noby

Brown Steve Madden Noby

+1

Brand Name: Steve Madden
Product Name: Noby
Gender: Men's
Color: Brown Leather
Price: $87.00MSRP: $150.0042% OFF
Rating: 4Rated 4 stars out of 5(2)

Josef Seibel - Erroll 50. Color Black. On sale for $136.95. MSRP $165.00. 17% off.

Black Josef Seibel Erroll 50

Black Josef Seibel Erroll 50

+2 colors/patterns

Brand Name: Josef Seibel
Product Name: Erroll 50
Gender: Men's
Color: Black
Price: $136.95MSRP: $165.0017% OFF
Rating

Josef Seibel - Erroll 52 Boots. Color Moro. On sale for $161.00. MSRP $175.00. 8% off. 5.0 out of 5 stars

Brown Josef Seibel Erroll 52 Boots

Brown Josef Seibel Erroll 52 Boots

+2

Brand Name: Josef Seibel
Product Name: Erroll 52 Boots
Gender: Men's
Color: Moro
Price: $161.00MSRP: $175.008% OFF
Rating: 5Rated 5 stars out of 5(1)

Tommy Hilfiger - Berton. Color Black. On sale for $79.57. MSRP $109.00. 27% off.

Black Tommy Hilfiger Berton

Black Tommy Hilfiger Berton

+2

Brand Name: Tommy Hilfiger
Product Name: Berton
Gender: Men's
Color: Black
Price: $79.57MSRP: $109.0027% OFF
Rating

Rockport - Caspe. Color Black Leather. On sale for $109.29. MSRP $149.95. 27% off. 5.0 out of 5 stars

Black Rockport Caspe

Black Rockport Caspe

+3

Brand Name: Rockport
Product Name: Caspe
Gender: Men's
Color: Black Leather
Price: $109.29MSRP: $149.9527% OFF
Rating: 5Rated 5 stars out of 5(1)

Mephisto - Fosco. Color Tobacco. Low Stock. On sale for $377.52. MSRP $429.00. 12% off.

Low Stock

Brown Mephisto Fosco

Brown Mephisto Fosco

+2

Brand Name: Mephisto
Product Name: Fosco
Gender: Men's
Color: Tobacco
Price: $377.52MSRP: $429.0012% OFF
Rating

SOREL - Buxton™ Lite Lace Plus Waterproof. Color Black/Black. Low Stock. On sale for $91.77. MSRP $135.00. 32% off. 3.0 out of 5 stars

Low Stock

Black SOREL Buxton™ Lite Lace Plus Waterproof

Black SOREL Buxton™ Lite Lace Plus Waterproof

+2

Brand Name: SOREL
Product Name: Buxton™ Lite Lace Plus Waterproof
Gender: Men's
Color: Black/Black
Price: $91.77MSRP: $135.0032% OFF
Rating: 3Rated 3 stars out of 5(1)

Thorogood - American Heritage Independence Square Toe Waterproof Safety. Color Crazy Horse. Low Stock. On sale for $244.95. MSRP $280.00. 13% off. 1.5 out of 5 stars

Low Stock

Brown Thorogood American Heritage Independence Square Toe Waterproof Safety

Brown Thorogood American Heritage Independence Square Toe Waterproof Safety

Brand Name: Thorogood
Product Name: American Heritage Independence Square Toe Waterproof Safety
Gender: Men's
Color: Crazy Horse
Price: $244.95MSRP: $280.0013% OFF
Rating: 2Rated 2 stars out of 5(2)

Dansko - Stephanie. Color Black Waterproof Suede. On sale for $132.96. MSRP $189.99. 30% off. 3.7 out of 5 stars

Black Dansko Stephanie

Black Dansko Stephanie

Brand Name: Dansko
Product Name: Stephanie
Gender: Women's
Color: Black Waterproof Suede
Price: $132.96MSRP: $189.9930% OFF
Rating: 4Rated 4 stars out of 5(6)

Polo Ralph Lauren - Bryson Chelsea Boot. Color Brown 1. On sale for $198.00. MSRP $228.00. 13% off. 3.8 out of 5 stars

Brown Polo Ralph Lauren Bryson Chelsea Boot

Brown Polo Ralph Lauren Bryson Chelsea Boot

+2

Brand Name: Polo Ralph Lauren
Product Name: Bryson Chelsea Boot
Gender: Men's
Color: Brown 1
Price: $198.00MSRP: $228.0013% OFF
Rating: 4Rated 4 stars out of 5(4)

Timberland - Britton Road Mid Lace Up Waterproof. Color Burgundy Full Grain. On sale for $152.71. MSRP $170.00. 10% off. 4.6 out of 5 stars

Mahogany Timberland Britton Road Mid Lace Up Waterproof

Mahogany Timberland Britton Road Mid Lace Up Waterproof

+4

Brand Name: Timberland
Product Name: Britton Road Mid Lace Up Waterproof
Gender: Men's
Color: Burgundy Full Grain
Price: $152.71MSRP: $170.0010% OFF
Rating: 5Rated 5 stars out of 5(31)

Volcom - Street Shield Slip-On Station Tactical Boots. Color Black. On sale for $134.95. MSRP $160.00. 16% off.

Black Volcom Street Shield Slip-On Station Tactical Boots

Black Volcom Street Shield Slip-On Station Tactical Boots

Brand Name: Volcom
Product Name: Street Shield Slip-On Station Tactical Boots
Gender: Men's
Color: Black
Price: $134.95MSRP: $160.0016% OFF
Rating

SOREL - Mac Hill™ Lite Mid Plus Waterproof. Color Black/Quarry. Low Stock. On sale for $105.00. MSRP $175.00. 40% off. 4.0 out of 5 stars

Low Stock

Black SOREL Mac Hill™ Lite Mid Plus Waterproof

Black SOREL Mac Hill™ Lite Mid Plus Waterproof

+2

Brand Name: SOREL
Product Name: Mac Hill™ Lite Mid Plus Waterproof
Gender: Men's
Color: Black/Quarry
Price: $105.00MSRP: $175.0040% OFF
Rating: 4Rated 4 stars out of 5(4)

Rocky - Rebound Wedge Composite Toe. Color Brown. Low Stock. On sale for $198.00. MSRP $208.00. 5% off. 3.2 out of 5 stars

Low Stock

Brown Rocky Rebound Wedge Composite Toe

Brown Rocky Rebound Wedge Composite Toe

Brand Name: Rocky
Product Name: Rebound Wedge Composite Toe
Gender: Men's
Color: Brown
Price: $198.00MSRP: $208.005% OFF
Rating: 3Rated 3 stars out of 5(18)

Join Our List, Get 10% Off

Sign up for Zappos emails—new subscribers get 10% off a future order!* Plus, get early access to sales, coupons, and more. (One code per email address.)