Best Seller
Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 EE)

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 EE)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Men's TREVINO Ankle Boots by Drew in Black Leather (Size 10 1/2 D)

Men's TREVINO Ankle Boots by Drew in Black Leather (Size 10 1/2 D)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Best Seller
Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EE)

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EE)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Womens

Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Womens

Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... more

$69.99

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Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 557201

Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 557201

The Danner Bull Run Chelsea Work Boots provide electrical hazard protection to ASTM F2892-18 EH standards and feature a durable, oiled, full grain leather upper. These boots are both durable and comfortable, with slip on action, making them perfect for... more

$229.95

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Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 168992

Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 168992

The Danner Bull Run Chelsea Work Boots provide electrical hazard protection to ASTM F2892-18 EH standards and feature a durable, oiled, full grain leather upper. These boots are both durable and comfortable, with slip on action, making them perfect for... more

$229.95

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Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 562692

Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 562692

The Danner Bull Run Chelsea Work Boots provide electrical hazard protection to ASTM F2892-18 EH standards and feature a durable, oiled, full grain leather upper. These boots are both durable and comfortable, with slip on action, making them perfect for... more

$229.95

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Michael Kors Rue Snake Embossed Leather Ankle Boot Black 8

Michael Kors Rue Snake Embossed Leather Ankle Boot Black 8

Show off your wild side in our Rue ankle boot. Crafted from snake-embossed leather, they’re finished with a sleek almond-shape pointed toe and stiletto heels. We love this eye-catching bootie with just about anything—pair it with a printed dress for a... more

$215.00 $44.44

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Chelsea Boots, Ankle Boots

Chelsea Boots, Ankle Boots

Men's Santoni Chelsea Boots, Ankle Boots - Blue - Casual boots Chelsea' suede ankle boots with elastic side inserts, contrast lining, back logo tab and rubber sole. Colours: Blue Composition: 100% leather Dimension: UK MEN MPN: MGSI13414SMAISYWU60.... more

$696.00 $454.00

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Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

Reposhing This Item I Purchased From @Cooldudz. Used 1x For A Wedding Rehearsal And Now That I Am Working From Home I Don’t Wear/Need Heels Anymore. Loved Them, Fit Well And Very Stylish. more

$50.00

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Xtratuf Leather Ankle Deck Boot Lace Shoe - Men's Black 8.5 LAL-000-BLK-085

Xtratuf Leather Ankle Deck Boot Lace Shoe - Men's Black 8.5 LAL-000-BLK-085

Xtratuf Leather Ankle Deck Boot Lace Shoe - Men's Black 8.5 LAL-000-BLK-085. To ensure these Men's Boots & Footwear by XTRATUF last a long time they're made from 100percent waterproof leather. Plus these Xtratuf Leather Ankle Deck Boots w/ Lace Insert... more

$125.00

FREE shipping

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Shield Square-toe Chelsea Ankle Boots

Shield Square-toe Chelsea Ankle Boots

Men's Burberry Shield Square-toe Chelsea Ankle Boots - Black - Casual boots 65% Calf Leather, 25% Polyester, 10% Rubber, Lining: 70% Calf Leather, 12% Polyester, 10% Goatskin Leather, 8% Rubber. Made in Italy. more

$1,106.62 $885.29

FREE shipping

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Henry Ankle Chelsea Boot

Henry Ankle Chelsea Boot

Men's Tricker's Henry Ankle Chelsea Boot - Black - Casual boots 100% Leather. Made in Italy. more

$732.05 $597.36

FREE shipping

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J. Crew Shoes | J. Crew Gray Leather Ankle Chelsea Boot W/ Ankle Strap And Gold Hardware- Size 8 | Color: Gray | Size: 8

J. Crew Shoes | J. Crew Gray Leather Ankle Chelsea Boot W/ Ankle Strap And Gold Hardware- Size 8 | Color: Gray | Size: 8

J. Crew Gray Leather Chelsea Ankle Boot. Made In Italy With 2 Inch Heel, Ankle Strap And Gold Hardware. 03868 Color: Gray Size: Women's 8 more

$36.00

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Free People Shoes | Free People James Chelsea Boots White Leather Lug Sole Ankle Boots In Bone 40 | Color: White | Size: 9

Free People Shoes | Free People James Chelsea Boots White Leather Lug Sole Ankle Boots In Bone 40 | Color: White | Size: 9

Brand: Free People Style: James Chelsea Boots Heeled Ankle Booties Color: White Material: Leather With Rubber Gum Sole Size: Eu 40, Fits Like A 9 Has A Slightly Narrow Fit In My Opinion, Though I Do Better With Wider Fit Shoes Condition: New, No Box.... more

$54.00

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Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Medium Brown 10.5 GB00353-105M

Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Medium Brown 10.5 GB00353-105M

Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Medium Brown 10.5 GB00353-105M. The new Georgia Boot AMP LT Wedge Work Boots start out with durable pasture proof SPR leather just like their classic wedges but then we pack on... more

$187.00

FREE shipping

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Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Wide Brown 10.5 GB00353-105W

Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Wide Brown 10.5 GB00353-105W

Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Wide Brown 10.5 GB00353-105W. The new Georgia Boot AMP LT Wedge Work Boots start out with durable pasture proof SPR leather just like their classic wedges but then we pack on the... more

$187.00

FREE shipping

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Michael Kors Rue Logo and Leather Boot Brown 9.5

Michael Kors Rue Logo and Leather Boot Brown 9.5

Step forward in a sleek pair of ankle boots you’ll be reaching for on nights out. Crafted from a combination of leather and Signature-print canvas, the Rue features a sharp pointed toe and rest on a slim stiletto heel. Complement yours with all-black... more

$195.00 $55.69

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Michael Kors Rue Logo and Leather Boot Brown 7

Michael Kors Rue Logo and Leather Boot Brown 7

Step forward in a sleek pair of ankle boots you’ll be reaching for on nights out. Crafted from a combination of leather and Signature-print canvas, the Rue features a sharp pointed toe and rest on a slim stiletto heel. Complement yours with all-black... more

$195.00 $55.69

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Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 EE)

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 EE)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Men's TREVINO Ankle Boots by Drew in Black Leather (Size 10 EEEE)

Men's TREVINO Ankle Boots by Drew in Black Leather (Size 10 EEEE)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Men's TREVINO Ankle Boots by Drew in Black Leather (Size 10 6E)

Men's TREVINO Ankle Boots by Drew in Black Leather (Size 10 6E)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EEEE)

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EEEE)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Men's TREVINO Ankle Boots by Drew in Black Leather (Size 11 1/2 D)

Men's TREVINO Ankle Boots by Drew in Black Leather (Size 11 1/2 D)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 EEEE)

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 EEEE)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Men's TREVINO Ankle Boots by Drew in Black Leather (Size 9 1/2 D)

Men's TREVINO Ankle Boots by Drew in Black Leather (Size 9 1/2 D)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 D)

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 D)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 1/2 D)

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 1/2 D)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Men's Murphy Casual Boots by Drew in Camel Leather (Size 10 M)

Men's Murphy Casual Boots by Drew in Camel Leather (Size 10 M)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The... more

$280.99

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Men's Murphy Casual Boots by Drew in Camel Leather (Size 8 1/2 6E)

Men's Murphy Casual Boots by Drew in Camel Leather (Size 8 1/2 6E)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The... more

$286.99

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Men's Murphy Casual Boots by Drew in Camel Leather (Size 9 4W)

Men's Murphy Casual Boots by Drew in Camel Leather (Size 9 4W)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The... more

$286.99

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Men's Murphy Casual Boots by Drew in Camel Leather (Size 15 6E)

Men's Murphy Casual Boots by Drew in Camel Leather (Size 15 6E)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The... more

$286.99

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Men's Murphy Casual Boots by Drew in Black Nubuck Leather (Size 13 4W)

Men's Murphy Casual Boots by Drew in Black Nubuck Leather (Size 13 4W)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The... more

$286.99

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Men's TREVINO Ankle Boots by Drew in Black Leather (Size 14 D)

Men's TREVINO Ankle Boots by Drew in Black Leather (Size 14 D)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 D)

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 D)

Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

$220.99

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Wide Width Men's Murphy Casual Boots by Drew in Black Nubuck Leather (Size 11 W)

Wide Width Men's Murphy Casual Boots by Drew in Black Nubuck Leather (Size 11 W)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The... more

$286.99

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Men's Murphy Casual Boots by Drew in Black Nubuck Leather (Size 11 4W)

Men's Murphy Casual Boots by Drew in Black Nubuck Leather (Size 11 4W)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The... more

$286.99

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Men's Murphy Casual Boots by Drew in Camel Leather (Size 13 6E)

Men's Murphy Casual Boots by Drew in Camel Leather (Size 13 6E)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The... more

$286.99

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Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Black (Size 11 1/2 W)

Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Black (Size 11 1/2 W)

A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

$89.95

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Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 11 W)

Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 11 W)

A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

$89.95

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More information about Men's Shoes

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