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Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10 Wide DDB0248-10-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10 Wide DDB0248-10-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

Theo Chukka Boot

Men's Thomas & Vine Theo Chukka Boot - Brown - Casual boots The Theo chukka boot from Thomas & Vine is a happy medium between casual and formal. Boasting a low-cut profile, this boot showcases 12mm Tru Comfort Foam insole that delivers cushioned... more

Livingston Chukka Boot

Men's Taft Livingston Chukka Boot - Brown - Casual boots Dare to experiment with the bold Livingston Chukka boot from Taft. Camo-printed inlays give an offbeat look to the clean leather upper of this chukka boot. Brogue accentuation elevates the style,... more

Aldridge Chukka Boot

Men's Thomas & Vine Aldridge Chukka Boot - Brown - Casual boots The Aldridge chukka boot from Thomas & Vine is an essential footwear for casual occasions. This lace-up shoe includes an embossed suede heel for added flair and a second pair of contrast... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Medium DDB0248-11-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Medium DDB0248-11-M. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Wide DDB0248-105-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Wide DDB0248-105-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Wide DDB0248-11-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Wide DDB0248-11-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

Carhartt Shoes | Carhartt Cmx4023 Lightweight Wedge Moc Toe Oil Tanned Chukka Boots | 10.5 W | Color: Brown/Tan | Size: 10.5

Carhartt Cmx4023 Lightweight Wedge Moc Toe Oil Tanned Chukka Boots | 10.5 W Men's Lightweight Work Boots For Everyday Wear. Leather Durability And Sneaker Comfort. These Lightweight Boots Blend A Stitched-Leather Upper And Cushioned Sneaker-Like... more

Carhartt Shoes | Men's Lightweight Wedge 4" Moc Toe Chukka Boots Size 8.5 | Color: Brown | Size: 8.5

Mfr # Cmx4023-9 Size 8.5 Description Elevate Your Casual Ensemble With The Men's Lightweight Wedge Moc Toe Chukka Boots. Merging The Timeless Elegance Of A Classic Leather Upper With Modern Comforts, These Boots Feature A Lightweight Cmeva Midsole And... more

Carhartt Shoes | Carhartt Mens Size 9.5 Lightweight Wedge Leather Chukka 4'' Work Boots Cmx4033 | Color: Brown | Size: 9.5

Carhartt Mens Size 9.5 Lightweight Wedge Leather Chukka 4'' Work Boots Cmx4033 more

Vance Co. Shoes Arturo Plain Toe Chukka Boot - Brown - 13

Introducing Arturo by Vance Co., the ankle boot that offers a classic look with modern comfort. Made with vegan leather and featuring an almond-toe and lace-up design, Arturo adds a touch of sophistication to any outfit. The lightweight EVA outsole, 12... more

Thomas and Vine Thomas & Vine Keegan Plain Toe Chukka Boot - Brown - 12

Casual enough for every day, suave enough for dinner, the Keegan by Thomas & Vine. This handsome round-toe chukka boot features genuine leather or suede uppers and a two-eye lace-up closure with a second pair of interchangeable laces. An 8 mm Tru... more

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Brown - 14

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

Lodge Plain Toe Chukka Boot - Brown - Florsheim Boots

Men's Florsheim Lodge Plain Toe Chukka Boot - Brown - Casual boots The clean design of the Florsheim Lodge Plain Toe Chukka Boot is highlighted by simple stitching details and a modern silhouette. Smooth leather upper with a burnished toe. Lace-up... more

Walkabout Men's Chukka - 8 Brown Boot E2

*This lightweight leather chukka features all the comfort, cushioning and flexibility of a quality walking shoe *Leather upper *Velcro® closure for easy on/off *FOOTONIC® II contoured cushioned insert is removable *Shock-absorbing EVA-TECH®... more

Nunn Bush Otto Plain Toe Chukka - Mens 12 Brown Boot XW

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

Nunn Bush Otto Plain Toe Chukka - Mens 9 Brown Boot XW

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

Kenetrek Mountain Extremes 10" Insulated Hunting Boots Leather and Nylon Men's, Brown SKU - 546164

A serious boot for rugged terrain, the 10 KenetrekMountain Extreme is made with a one piece vamp of 2.8 mm top grain leather on top of stiff nylon midsoles with high traction K-Talon outsoles. A waterproof, breathable Windtex membrane keeps you warm... more

Men's ROCKFORD Boots by Drew in Dark Brown (Size 9 1/2 EE)

From Drew® - Rockford boots uniquely comfortable. These popular orthotic boots offer double the added depth complements of the two removable footbeds found in the patented Plus Fitting System®. Ideal for extra-thick orthotics, they accommodate for even... more

Men's ROCKFORD Boots by Drew in Dark Brown (Size 9 1/2 EEEE)

From Drew® - Rockford boots uniquely comfortable. These popular orthotic boots offer double the added depth complements of the two removable footbeds found in the patented Plus Fitting System®. Ideal for extra-thick orthotics, they accommodate for even... more

Men's ROCKFORD Boots by Drew in Dark Brown (Size 10 1/2 EE)

From Drew® - Rockford boots uniquely comfortable. These popular orthotic boots offer double the added depth complements of the two removable footbeds found in the patented Plus Fitting System®. Ideal for extra-thick orthotics, they accommodate for even... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Wide DDB0248-13-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Wide DDB0248-13-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

Crewson Crazy Horse Leather Chukka Boots

Men's Dr. Martens Crewson Crazy Horse Leather Chukka Boots - Brown - Casual boots Taking cues from our 6-eye 101 silhouette, the Crewson Chukka boot unites our heritage markings in one of our lightest ever constructions. Engineered with functionality... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Wide DDB0248-105-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Wide DDB0248-105-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Medium DDB0248-11-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Medium DDB0248-11-M. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Medium DDB0248-13-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Medium DDB0248-13-M. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 12 Wide DDB0248-12-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 12 Wide DDB0248-12-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9.5 Medium DDB0248-95-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9.5 Medium DDB0248-95-M. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9 Medium DDB0248-9-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9 Medium DDB0248-9-M. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9 Wide DDB0248-9-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 9 Wide DDB0248-9-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank and... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 12 Wide DDB0248-12-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 12 Wide DDB0248-12-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Wide DDB0248-13-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Wide DDB0248-13-W. It has a soft mesh lining inside and the X-treme comfort removable polyurethane footbed with memory foam. It also has a cushion flex insole fiberglass shank... more

Davis Square Chukka Boot

Men's Timberland Davis Square Chukka Boot - Brown - Casual boots Elevate your casual wardrobe with the Davis Square chukka boot from Timberland. The plush trim on the collar lend a cozy touch, while the Defender Repellent Systems treatment deters... more

Columbia Shoes | Columbia 10 Irvington Ii Chukka Leather Waterproof Ankle Boots Winter Brown Lace | Color: Brown | Size: 10

Columbia Mens 10 Irvington Ii Chukka Leather Waterproof Boots Winter Brown Lace Rubber Sole Lace Up Ankle Boots Solid Non-Marking Rubber Outsole Techlite Lightweight Cushioned Midsole Waterproof Leather Boot With An Ultra-Cushioned Midsole Is Made For... more

Thomas and Vine Thomas & Vine Keegan Plain Toe Chukka Boot - Brown - 13

Casual enough for every day, suave enough for dinner, the Keegan by Thomas & Vine. This handsome round-toe chukka boot features genuine leather or suede uppers and a two-eye lace-up closure with a second pair of interchangeable laces. An 8 mm Tru... more

Vance Co. Shoes Arturo Plain Toe Chukka Boot - Brown - 13

Introducing Arturo by Vance Co., the ankle boot that offers a classic look with modern comfort. Made with vegan leather and featuring an almond-toe and lace-up design, Arturo adds a touch of sophistication to any outfit. The lightweight EVA outsole, 12... more

Thomas and Vine Thomas & Vine Keegan Plain Toe Chukka Boot - Brown - 10

Casual enough for every day, suave enough for dinner, the Keegan by Thomas & Vine. This handsome round-toe chukka boot features genuine leather or suede uppers and a two-eye lace-up closure with a second pair of interchangeable laces. An 8 mm Tru... more

Vance Co. Shoes Arturo Plain Toe Chukka Boot - Brown - 10

Introducing Arturo by Vance Co., the ankle boot that offers a classic look with modern comfort. Made with vegan leather and featuring an almond-toe and lace-up design, Arturo adds a touch of sophistication to any outfit. The lightweight EVA outsole, 12... more