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

Size 14 Ankle Leather Shoes On Sale

45 items found

Sort By

Your Selections

Search Results

Nunn Bush - Odell 2.0 Wingtip Dress Casual Chukka Leather Boot. Color Black. On sale for $89.95. MSRP $120.00. 25% off. 4.6 out of 5 stars

Black Nunn Bush Odell 2.0 Wingtip Dress Casual Chukka Leather Boot

Black 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: Black
Price: $89.95MSRP: $120.0025% OFF
Rating: 5Rated 5 stars out of 5(9)

Nunn Bush - Otis 2.0 Chelsea Fashion Leather Boot. Color Brown. On sale for $89.95. MSRP $120.00. 25% 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: $89.95MSRP: $120.0025% OFF
Rating: 4Rated 4 stars out of 5(6)

Born - Hemlock. Color Black Full Grain. On sale for $134.95. MSRP $145.00. 7% off. 4.3 out of 5 stars

Black Born Hemlock

Black Born Hemlock

+2

Brand Name: Born
Product Name: Hemlock
Gender: Men's
Color: Black Full Grain
Price: $134.95MSRP: $145.007% OFF
Rating: 4Rated 4 stars out of 5(189)

Clarks - Shepton Easy. Color Black Leather. On sale for $77.96. MSRP $120.00. 35% off.

Black Clarks Shepton Easy

Black Clarks Shepton Easy

+2

Brand Name: Clarks
Product Name: Shepton Easy
Gender: Men's
Color: Black Leather
Price: $77.96MSRP: $120.0035% OFF
Rating

Dunham - Brisco. Color Black Leather. On sale for $111.96. MSRP $159.95. 30% off. 4.0 out of 5 stars

Black Dunham Brisco

Black Dunham Brisco

+3

Brand Name: Dunham
Product Name: Brisco
Gender: Men's
Color: Black Leather
Price: $111.96MSRP: $159.9530% OFF
Rating: 4Rated 4 stars out of 5(1)

Dr. Martens - 101. Color Dark Brown Crazy Horse. On sale for $120.00. MSRP $160.00. 25% off. 4.7 out of 5 stars

Brown Dr. Martens 101

Brown Dr. Martens 101

Brand Name: Dr. Martens
Product Name: 101
Gender: Unisex
Color: Dark Brown Crazy Horse
Price: $120.00MSRP: $160.0025% OFF
Rating: 5Rated 5 stars out of 5(6)

Florsheim - Rucci Plain Toe Chukka Boot. Color Black Smooth. On sale for $117.63. MSRP $155.00. 24% 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: $117.63MSRP: $155.0024% OFF
Rating: 4Rated 4 stars out of 5(45)

Dr. Martens - 1460 Pascal Bex. Color Black Pisa. On sale for $149.95. MSRP $180.00. 17% off. 4.4 out of 5 stars

Black Dr. Martens 1460 Pascal Bex

Black Dr. Martens 1460 Pascal Bex

Brand Name: Dr. Martens
Product Name: 1460 Pascal Bex
Gender: Unisex
Color: Black Pisa
Price: $149.95MSRP: $180.0017% OFF
Rating: 4Rated 4 stars out of 5(42)

Dr. Martens - Anistone Lo Leather Boots. Color Sand. On sale for $135.96. MSRP $170.00. 20% off.

Beige Dr. Martens Anistone Lo Leather Boots

Beige Dr. Martens Anistone Lo Leather Boots

Brand Name: Dr. Martens
Product Name: Anistone Lo Leather Boots
Gender: Unisex
Color: Sand
Price: $135.96MSRP: $170.0020% OFF
Rating

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(5)

Stacy Adams - Henry Cap Toe Lace-Up Boot. Color Black. On sale for $148.50. MSRP $165.00. 10% off. 5.0 out of 5 stars

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: $148.50MSRP: $165.0010% OFF
Rating: 5Rated 5 stars out of 5(2)

Florsheim - Rucci Plain Toe Chukka. Color Cognac. On sale for $94.77. MSRP $155.00. 39% off. 4.9 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: $94.77MSRP: $155.0039% OFF
Rating: 5Rated 5 stars out of 5(11)

Timberland PRO - PRO Wedge 6 Inch Moc Soft Toe. Color Rust. On sale for $124.95. MSRP $145.00. 14% off. 4.2 out of 5 stars

Orange Timberland PRO PRO Wedge 6 Inch Moc Soft Toe

Orange Timberland PRO PRO Wedge 6 Inch Moc Soft Toe

Brand Name: Timberland PRO
Product Name: PRO Wedge 6 Inch Moc Soft Toe
Gender: Men's
Color: Rust
Price: $124.95MSRP: $145.0014% OFF
Rating: 4Rated 4 stars out of 5(211)

Dr. Martens - Hardie II. Color Black Pit Quarter. On sale for $109.95. MSRP $120.00. 8% off. 4.4 out of 5 stars

Black Dr. Martens Hardie II

Black Dr. Martens Hardie II

+2

Brand Name: Dr. Martens
Product Name: Hardie II
Gender: Unisex
Color: Black Pit Quarter
Price: $109.95MSRP: $120.008% OFF
Rating: 4Rated 4 stars out of 5(22)

Frye - The Safety-Crafted Wellington Work Boots. Color Dark Brown. On sale for $131.94. MSRP $206.00. 36% 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: $131.94MSRP: $206.0036% OFF
Rating

Rockport - Ezra Waterproof Boots. Color Taupe Leather. On sale for $119.29. MSRP $159.95. 25% off. 2.5 out of 5 stars

Taupe Rockport Ezra Waterproof Boots

Taupe Rockport Ezra Waterproof Boots

+3

Brand Name: Rockport
Product Name: Ezra Waterproof Boots
Gender: Men's
Color: Taupe Leather
Price: $119.29MSRP: $159.9525% OFF
Rating: 3Rated 3 stars out of 5(2)

Dr. Martens - Church Quad Archive. Color Dark Brown Crazy Horse. On sale for $120.00. MSRP $200.00. 40% off. 3.8 out of 5 stars

Brown Dr. Martens Church Quad Archive

Brown Dr. Martens Church Quad Archive

Brand Name: Dr. Martens
Product Name: Church Quad Archive
Gender: Unisex
Color: Dark Brown Crazy Horse
Price: $120.00MSRP: $200.0040% OFF
Rating: 4Rated 4 stars out of 5(4)

Dr. Martens - 1460 Crazy Horse Leather Boots. Color Dark Brown Crazy Horse. On sale for $139.95. MSRP $170.00. 18% off. 4.4 out of 5 stars

Brown Dr. Martens 1460 Crazy Horse Leather Boots

Brown Dr. Martens 1460 Crazy Horse Leather Boots

Brand Name: Dr. Martens
Product Name: 1460 Crazy Horse Leather Boots
Gender: Unisex
Color: Dark Brown Crazy Horse
Price: $139.95MSRP: $170.0018% OFF
Rating: 4Rated 4 stars out of 5(33)

Carhartt - Gilmore WP 6" Boot. Color Coyote Nubuck. On sale for $109.34. MSRP $174.99. 38% off. 3.9 out of 5 stars

Pewter Carhartt Gilmore WP 6" Boot

Pewter Carhartt Gilmore WP 6" Boot

Brand Name: Carhartt
Product Name: Gilmore WP 6" Boot
Gender: Men's
Color: Coyote Nubuck
Price: $109.34MSRP: $174.9938% OFF
Rating: 4Rated 4 stars out of 5(9)

Dr. Martens - 2976 Platform Faux-Fur Lined. Color Black. On sale for $154.00. MSRP $220.00. 30% off. 4.1 out of 5 stars

Black Dr. Martens 2976 Platform Faux-Fur Lined

Black Dr. Martens 2976 Platform Faux-Fur Lined

Brand Name: Dr. Martens
Product Name: 2976 Platform Faux-Fur Lined
Gender: Unisex
Color: Black
Price: $154.00MSRP: $220.0030% OFF
Rating: 4Rated 4 stars out of 5(15)

Ariat - Rebar Wedge Pull-On Waterproof Composite Toe Work Boots. Color Distressed Brown. On sale for $199.95. MSRP $209.95. 5% off. 4.1 out of 5 stars

Brown Ariat Rebar Wedge Pull-On Waterproof Composite Toe Work Boots

Brown Ariat Rebar Wedge Pull-On Waterproof Composite Toe Work Boots

Brand Name: Ariat
Product Name: Rebar Wedge Pull-On Waterproof Composite Toe Work Boots
Gender: Men's
Color: Distressed Brown
Price: $199.95MSRP: $209.955% OFF
Rating: 4Rated 4 stars out of 5(19)

Hey Dude - Branson Classic. Color Black/Black. On sale for $85.45. MSRP $94.95. 10% off. 4.2 out of 5 stars

Black Hey Dude Branson Classic

Black Hey Dude Branson Classic

+2

Brand Name: Hey Dude
Product Name: Branson Classic
Gender: Men's
Color: Black/Black
Price: $85.45MSRP: $94.9510% OFF
Rating: 4Rated 4 stars out of 5(38)

Dr. Martens - 1460 Bex. Color Dark Brown Crazy Horse. On sale for $159.95. MSRP $180.00. 11% off. 3.6 out of 5 stars

Brown Dr. Martens 1460 Bex

Brown Dr. Martens 1460 Bex

Brand Name: Dr. Martens
Product Name: 1460 Bex
Gender: Unisex
Color: Dark Brown Crazy Horse
Price: $159.95MSRP: $180.0011% OFF
Rating: 4Rated 4 stars out of 5(37)

Dr. Martens - 2976 Quad Chelsea. Color Cherry Red. On sale for $199.92. MSRP $210.00. 5% off.

Red Dr. Martens 2976 Quad Chelsea

Red Dr. Martens 2976 Quad Chelsea

Brand Name: Dr. Martens
Product Name: 2976 Quad Chelsea
Gender: Unisex
Color: Cherry Red
Price: $199.92MSRP: $210.005% OFF
Rating

Volcom - Street Shield Slip-On Station Tactical Boots. Color Black. On sale for $134.95. MSRP $160.00. 16% off. 4.0 out of 5 stars

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: 4Rated 4 stars out of 5(2)

KEEN - Targhee Lace High Polar Waterproof Insulated. Color Black/Raven. On sale for $182.70. MSRP $189.95. 4% off. 4.0 out of 5 stars

Black KEEN Targhee Lace High Polar Waterproof Insulated

Black KEEN Targhee Lace High Polar Waterproof Insulated

Brand Name: KEEN
Product Name: Targhee Lace High Polar Waterproof Insulated
Gender: Men's
Color: Black/Raven
Price: $182.70MSRP: $189.954% OFF
Rating: 4Rated 4 stars out of 5(49)

Ariat - Longview Shock Shield 8" Waterproof Work Boots. Color Copper Brown. On sale for $189.95. MSRP $199.95. 5% off.

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: $189.95MSRP: $199.955% OFF
Rating

Ariat - Rebar Flex SD Composite Toe Work Boots. Color Distressed Brown/Stone. On sale for $199.95. MSRP $209.95. 5% off.

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: $199.95MSRP: $209.955% OFF
Rating

Dr. Martens Work - 1460 SR 8-Tie Boot. Color Black. On sale for $169.95. MSRP $180.00. 6% off. 3.5 out of 5 stars

Black Dr. Martens Work 1460 SR 8-Tie Boot

Black Dr. Martens Work 1460 SR 8-Tie Boot

Brand Name: Dr. Martens Work
Product Name: 1460 SR 8-Tie Boot
Gender: Unisex
Color: Black
Price: $169.95MSRP: $180.006% OFF
Rating: 3Rated 3 stars out of 5(40)

DieHard - Malibu 8" Soft Toe. Color Rust. Low Stock. On sale for $110.00. MSRP $175.95. 37% off.

Low Stock

Orange DieHard Malibu 8" Soft Toe

Orange DieHard Malibu 8" Soft Toe

Brand Name: DieHard
Product Name: Malibu 8" Soft Toe
Gender: Men's
Color: Rust
Price: $110.00MSRP: $175.9537% OFF
Rating

Ariat - Turbo Duratread 6" Waterproof Work Boots. Color Dark Brown. On sale for $159.95. MSRP $169.95. 6% off.

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: $159.95MSRP: $169.956% OFF
Rating

Ariat - Longview Shock Shield 8" Waterproof Composite Toe Work Boots. Color Copper Brown. On sale for $199.95. MSRP $209.95. 5% off.

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: $199.95MSRP: $209.955% OFF
Rating

Dr. Martens - 2976. Color Saddle Tan. On sale for $138.89. MSRP $180.00. 23% off. 3.4 out of 5 stars

Brown Dr. Martens 2976

Brown Dr. Martens 2976

+3

Brand Name: Dr. Martens
Product Name: 2976
Gender: Men's
Color: Saddle Tan
Price: $138.89MSRP: $180.0023% OFF
Rating: 3Rated 3 stars out of 5(11)

Johnston & Murphy - Raleigh Double Buckle Boots. Color Mahogany Full Grain. Low Stock. On sale for $166.50. MSRP $185.00. 10% off.

Low Stock

Brown Johnston & Murphy Raleigh Double Buckle Boots

Brown Johnston & Murphy Raleigh Double Buckle Boots

Brand Name: Johnston & Murphy
Product Name: Raleigh Double Buckle Boots
Gender: Men's
Color: Mahogany Full Grain
Price: $166.50MSRP: $185.0010% OFF
Rating

DieHard - Malibu CT 6". Color Rust. Low Stock. On sale for $110.00. MSRP $157.95. 30% off. 3.5 out of 5 stars

Low Stock

Orange DieHard Malibu CT 6"

Orange DieHard Malibu CT 6"

Brand Name: DieHard
Product Name: Malibu CT 6"
Gender: Men's
Color: Rust
Price: $110.00MSRP: $157.9530% OFF
Rating: 4Rated 4 stars out of 5(4)

Anthony Veer - Rockefeller Hiking Boot. Color Chocolate Brown. Low Stock. On sale for $124.19. MSRP $254.95. 51% off. 4.0 out of 5 stars

Low Stock

Brown Anthony Veer Rockefeller Hiking Boot

Brown Anthony Veer Rockefeller Hiking Boot

Brand Name: Anthony Veer
Product Name: Rockefeller Hiking Boot
Gender: Men's
Color: Chocolate Brown
Price: $124.19MSRP: $254.9551% OFF
Rating: 4Rated 4 stars out of 5(55)

Thorogood - American Heritage Independence Square Toe Waterproof Safety. Color Crazy Horse. Low Stock. On sale for $168.84. MSRP $280.00. 40% 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: $168.84MSRP: $280.0040% OFF
Rating: 2Rated 2 stars out of 5(2)

DieHard - Crusader WP CT 6" Boot. Color Rust. Low Stock. On sale for $110.00. MSRP $120.00. 8% off. 2.8 out of 5 stars

Low Stock

Orange DieHard Crusader WP CT 6" Boot

Orange DieHard Crusader WP CT 6" Boot

Brand Name: DieHard
Product Name: Crusader WP CT 6" Boot
Gender: Men's
Color: Rust
Price: $110.00MSRP: $120.008% OFF
Rating: 3Rated 3 stars out of 5(6)

Hey Dude - Tahoe Classic. Color Taupe Grey. On sale for $80.74. MSRP $94.99. 15% off. 4.4 out of 5 stars

Multi Hey Dude Tahoe Classic

Multi Hey Dude Tahoe Classic

+2

Brand Name: Hey Dude
Product Name: Tahoe Classic
Gender: Men's
Color: Taupe Grey
Price: $80.74MSRP: $94.9915% OFF
Rating: 4Rated 4 stars out of 5(180)

. Clarks - Shepton. Color Dark Brown Leather. On sale for $94.99. MSRP $100.00. 5% off. 2.0 out of 5 stars

Brown Clarks Shepton

Brown Clarks Shepton

+5

Brand Name: Clarks
Product Name: Shepton
Gender: Men's
Color: Dark Brown Leather
Price: $94.99MSRP: $100.005% OFF
Rating: 2Rated 2 stars out of 5(4)

Timberland PRO - Morphix 6" Composite Safety Toe Waterproof. Color Black/Red. On sale for $159.95. MSRP $170.00. 6% off. 4.0 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/Red
Price: $159.95MSRP: $170.006% OFF
Rating: 4Rated 4 stars out of 5(96)

Stacy Adams - Maury Cap Toe Chelsea Boot. Color Black. On sale for $91.00. MSRP $145.00. 37% off. 4.7 out of 5 stars

Black Stacy Adams Maury Cap Toe Chelsea Boot

Black Stacy Adams Maury Cap Toe Chelsea Boot

+3

Brand Name: Stacy Adams
Product Name: Maury Cap Toe Chelsea Boot
Gender: Men's
Color: Black
Price: $91.00MSRP: $145.0037% OFF
Rating: 5Rated 5 stars out of 5(41)

Dr. Martens - Combs Jungle Zip Casual Boots. Color Dark Khaki. On sale for $83.97. MSRP $140.00. 40% off. 2.5 out of 5 stars

Khaki Dr. Martens Combs Jungle Zip Casual Boots

Khaki Dr. Martens Combs Jungle Zip Casual Boots

+3

Brand Name: Dr. Martens
Product Name: Combs Jungle Zip Casual Boots
Gender: Unisex
Color: Dark Khaki
Price: $83.97MSRP: $140.0040% OFF
Rating: 3Rated 3 stars out of 5(2)

Dr. Martens - 1460 Pascal. Color Light Tan Mini Leopard Spot. On sale for $154.80. MSRP $180.00. 14% off. 4.4 out of 5 stars

Brown Dr. Martens 1460 Pascal

Brown Dr. Martens 1460 Pascal

Brand Name: Dr. Martens
Product Name: 1460 Pascal
Gender: Unisex
Color: Light Tan Mini Leopard Spot
Price: $154.80MSRP: $180.0014% OFF
Rating: 4Rated 4 stars out of 5(17)

Florsheim - Forge Plain Toe Gore Boot. Color Black. Low Stock. On sale for $116.95. MSRP $130.00. 10% off. 3.7 out of 5 stars

Low Stock

Black Florsheim Forge Plain Toe Gore Boot

Black Florsheim Forge Plain Toe Gore Boot

+2

Brand Name: Florsheim
Product Name: Forge Plain Toe Gore Boot
Gender: Men's
Color: Black
Price: $116.95MSRP: $130.0010% OFF
Rating: 4Rated 4 stars out of 5(12)

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.)