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Gaspen Chukka Boot

Gaspen Chukka Boot

Men's Crown Vintage Gaspen Chukka Boot - Green - Casual boots Transition from the weekend to the office with the Gaspen chukka boot from Crown Vintage. This pair features a classic silhouette and is elevated by detailed craftsmanship. What they are:... more

$59.99

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Gaspen Chukka Boot

Gaspen Chukka Boot

Men's Crown Vintage Gaspen Chukka Boot - Brown - Casual boots Transition from the weekend to the office with the Gaspen chukka boot from Crown Vintage. This pair features a classic silhouette and is elevated by detailed craftsmanship. What they are:... more

$59.99

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Best Seller
Tadesse Chukka Boot

Tadesse Chukka Boot

Men's Vince Camuto Tadesse Chukka Boot - Brown - Casual boots With a classic style made to pair well with a favorite professional or semi-formal fit, the Tadesse chukka boot is a great add to your wardrobe. The Flex 365 Technology keeps you extra... more

$178.99 $129.98

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J. Crew Shoes | J.Crew Brown Suede Chukka Desert Field Ankle Boot Lace Up Chunky 8.5 Preppy | Color: Brown | Size: 8.5

J. Crew Shoes | J.Crew Brown Suede Chukka Desert Field Ankle Boot Lace Up Chunky 8.5 Preppy | Color: Brown | Size: 8.5

J. Crew Desert Chukka Ankle Boots. Genuine Butter Soft Suede Upper In Dark Brown. Adjustable Laces. Round Toe. Made In Italy. Leather Lining. Crepe Rubber Sole. Chunky Rugged Classic Preppy Equestrian Casual Chic Collegiate Academia Timeless Retro... more

$50.00

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Levi's Shoes | Levi's Mens Dean Wx Ul Rugged Casual Hiker Chukka Boot | Color: Brown | Size: 11

Levi's Shoes | Levi's Mens Dean Wx Ul Rugged Casual Hiker Chukka Boot | Color: Brown | Size: 11

These Levi's Dean Wx Ul Men's Chukka Boots Feature A Synthetic Vegan Leather Upper With A Classic Hiker Design. Boot Features 6 Hole Lace-Up Closure With Rugged Metal Eyelets Lightly Padded Collar For Extra Comfort Subtle Levi's Logo And Tab Details... more

$59.00

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Levi's Shoes | Levi's "Dean Wx Ul" Men's Cedar/Brown Chukka Boot Size: 11 - New W/Tags | Color: Brown/Tan | Size: 11

Levi's Shoes | Levi's "Dean Wx Ul" Men's Cedar/Brown Chukka Boot Size: 11 - New W/Tags | Color: Brown/Tan | Size: 11

These Levi's Dean Wx Ul Men's Chukka Boots Feature A Synthetic Vegan Leather Upper With A Classic Hiker Design. Boot Features 6 Hole Lace-Up Closure With Rugged Metal Eyelets Lightly Padded Collar For Extra Comfort Subtle Levi's Logo And Tab Details... more

$50.00

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Gaspen Chukka Boot - Green - Crown Vintage Boots

Gaspen Chukka Boot - Green - Crown Vintage Boots

Men's Crown Vintage Gaspen Chukka Boot - Green - Casual boots Transition from the weekend to the office with the Gaspen chukka boot from Crown Vintage. This pair features a classic silhouette and is elevated by detailed craftsmanship. What they are:... more

$60.00

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® Neumel Weather Hybrid Suede/waterproof Classic Boots - Black - Ugg Boots

® Neumel Weather Hybrid Suede/waterproof Classic Boots - Black - Ugg Boots

Men's Ugg ® Neumel Weather Hybrid Suede/waterproof Classic Boots - Black - Casual boots Our iconic heritage chukka gets a weatherized upgrade. A timeless boot made of rich, waterproof suede, it's lined in our UGG®plush upcycled wool blend and finished... more

$180.00 $126.00

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Eastland Oscar - Mens 11 Grey Boot D

Eastland Oscar - Mens 11 Grey Boot D

*The classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style *Leather upper with a detailed stitched moc toe design *4" shaft height *Comfort leather sock lining and insole supports and conforms to the curves of your foot... more

$209.95

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Eastland Oscar - Mens 11.5 Grey Boot D

Eastland Oscar - Mens 11.5 Grey Boot D

*The classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style *Leather upper with a detailed stitched moc toe design *4" shaft height *Comfort leather sock lining and insole supports and conforms to the curves of your foot... more

$209.95

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Eastland Oscar - Mens 13 Grey Boot D

Eastland Oscar - Mens 13 Grey Boot D

*The classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style *Leather upper with a detailed stitched moc toe design *4" shaft height *Comfort leather sock lining and insole supports and conforms to the curves of your foot... more

$209.95

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Barbour Readhead Chukka Boot - Brown

Barbour Readhead Chukka Boot - Brown

A staple of their men's footwear range, the Barbour Readhead chukka boots are designed to be an effortless go-to for any smart casual look.Offered in a range of versatile leather and suede colours, the boots feature classic two eyelet styling with a... more

$276.00 $163.00

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Barbour Readhead Chukka Boot - Brown

Barbour Readhead Chukka Boot - Brown

A staple of their men's footwear range, the Barbour Readhead chukka boots are designed to be an effortless go-to for any smart casual look.Offered in a range of versatile leather and suede colours, the boots feature classic two eyelet styling with a... more

$276.00 $163.00

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Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(Black 11)

Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(Black 11)

Sleek lines and a classic design lends this men s lace-up shoe a look that s timeless and modern all at once. The durable rubber outsole has shock-absorbing properties and provides traction for enhanced stability. Goes with everything from suits and... more

$36.28

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Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(Black 5.5)

Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(Black 5.5)

Sleek lines and a classic design lends this men s lace-up shoe a look that s timeless and modern all at once. The durable rubber outsole has shock-absorbing properties and provides traction for enhanced stability. Goes with everything from suits and... more

$33.97

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Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(White 13)

Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(White 13)

Sleek lines and a classic design lends this men s lace-up shoe a look that s timeless and modern all at once. The durable rubber outsole has shock-absorbing properties and provides traction for enhanced stability. Goes with everything from suits and... more

$50.26

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Wide Width Men's Findley Chukka Boots by Propet in Black (Size 15 W)

Wide Width Men's Findley Chukka Boots by Propet in Black (Size 15 W)

Plain toe leather Chukka boot with detailed stitching. Long lasting high-density Open Cell foam breaths and allows air to circulate keeping feet naturally cool. Rubber outsole with cushioning EVA layer.FABRIC: Leather UpperRemovable footbedDetailes... more

$134.99

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Men's Findley Chukka Boots by Propet in Tan (Size 14 M)

Men's Findley Chukka Boots by Propet in Tan (Size 14 M)

Plain toe leather Chukka boot with detailed stitching. Long lasting high-density Open Cell foam breaths and allows air to circulate keeping feet naturally cool. Rubber outsole with cushioning EVA layer.FABRIC: Leather UpperRemovable footbedDetailes... more

$134.99

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Men's Findley Chukka Boots by Propet in Black (Size 12 M)

Men's Findley Chukka Boots by Propet in Black (Size 12 M)

Plain toe leather Chukka boot with detailed stitching. Long lasting high-density Open Cell foam breaths and allows air to circulate keeping feet naturally cool. Rubber outsole with cushioning EVA layer.FABRIC: Leather UpperRemovable footbedDetailes... more

$134.99

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Danner Pilgrim Chukka 4.5" Boots Leather Men's, Bracken SKU - 548397

Danner Pilgrim Chukka 4.5" Boots Leather Men's, Bracken SKU - 548397

The Danner Pilgrim Chukka 4.5 Boots features a premium, durable nubuck upper with 360-degree leather lined for comfort and natural moisture-wicking. The Low-density PU footbed offers lightweight cushioning and lasting durability and as well as a nylon... more

$159.95

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Muck Boots Fieldblazer Classic Hunting Boots Rubber and Nylon Men's, Mossy Oak Break-Up Country SKU - 747083

Muck Boots Fieldblazer Classic Hunting Boots Rubber and Nylon Men's, Mossy Oak Break-Up Country SKU - 747083

The Muck Fieldblazer Classic Hunting Boots are both comfortable and original. The Fieldblazer classic brings back the boot that started a revolution in the hunting industry. Refreshed with a new lining package that acts as both a safety and comfort... more

$145.00

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Muck Boots Fieldblazer Classic Hunting Boots Rubber and Nylon Men's, Mossy Oak Break-Up Country SKU - 510826

Muck Boots Fieldblazer Classic Hunting Boots Rubber and Nylon Men's, Mossy Oak Break-Up Country SKU - 510826

The Muck Fieldblazer Classic Hunting Boots are both comfortable and original. The Fieldblazer classic brings back the boot that started a revolution in the hunting industry. Refreshed with a new lining package that acts as both a safety and comfort... more

$145.00

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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

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

$141.50

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Muck Boots Chore Mid XpressCool Classic Work Boot - Men's Brown 9 CMCT-900-BRN-090

Muck Boots Chore Mid XpressCool Classic Work Boot - Men's Brown 9 CMCT-900-BRN-090

Muck Boots Chore Mid XpressCool Classic Work Boot - Men's Brown 9 CMCT-900-BRN-090. Muck Boots ensured these Men's Footwear are 100percent waterproof and constructed using a rugged Spandura upper that's nearly impossible to tear and these Muck Boot... more

$170.00

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

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

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

$141.50

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Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 13 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 13 M)

A chukka boot is a versatile yet stylish option and these Eastland® brand boots feature hand sewn construction and quality comfort. They have memory foam comfort insoles that support and conform to feet while the shock absorbing natural rubber outsole... more

$110.00

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Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 11 1/2 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 11 1/2 M)

A chukka boot is a versatile yet stylish option and these Eastland® brand boots feature hand sewn construction and quality comfort. They have memory foam comfort insoles that support and conform to feet while the shock absorbing natural rubber outsole... more

$110.00

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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

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

$141.50

FREE shipping

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Men's Findley Chukka Boots by Propet in Tan (Size 14 M)

Men's Findley Chukka Boots by Propet in Tan (Size 14 M)

Plain toe leather Chukka boot with detailed stitching. Long lasting high-density Open Cell foam breaths and allows air to circulate keeping feet naturally cool. Rubber outsole with cushioning EVA layer.FABRIC: Leather UpperRemovable footbedDetailes... more

$134.99

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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

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

$141.50

FREE shipping

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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

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

$141.50

FREE shipping

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Casper Chukka Boot

Casper Chukka Boot

Men's Crown Vintage Casper Chukka Boot - Brown - Casual boots Show off classic tailored appeal with the Casper chukka boot from Crown Vintage. This leather lace-up pairs perfectly with dark-wash denim and sweaters for date night. Leather upper. Lace-up... more

$44.99

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Bushacre Chukka Boot

Bushacre Chukka Boot

Men's Clarks Bushacre Chukka Boot - Brown - Casual boots Go for classic appeal in the Bushacre chukka boot from Clarks. The smooth leather upper and Ultimate Comfort footbed work together for high-quality style you can pair with any outfit. Leather or... more

$89.99

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Vandick Chukka Boot

Vandick Chukka Boot

Men's Sandro Moscoloni Vandick Chukka Boot - Black - Casual boots The Vandick chukka boot from Sandro Moscoloni proves a versatile must-have with a classic design to finish off favorite fits. This leather pair's cushioned footbed adds a comfortable... more

$198.99

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Vandick Chukka Boot

Vandick Chukka Boot

Men's Sandro Moscoloni Vandick Chukka Boot - Blue - Casual boots The Vandick chukka boot from Sandro Moscoloni proves a versatile must-have with a classic design to finish off favorite fits. This leather pair's cushioned footbed adds a comfortable... more

$198.99

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® Neumel Weather Hybrid Suede/waterproof Classic Boots

® Neumel Weather Hybrid Suede/waterproof Classic Boots

Men's Ugg ® Neumel Weather Hybrid Suede/waterproof Classic Boots - Black - Casual boots Our iconic heritage chukka gets a weatherized upgrade. A timeless boot made of rich, waterproof suede, it's lined in our UGG®plush upcycled wool blend and finished... more

$180.00 $125.99

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® Neumel Weather Hybrid Suede/waterproof Classic Boots

® Neumel Weather Hybrid Suede/waterproof Classic Boots

Men's Ugg ® Neumel Weather Hybrid Suede/waterproof Classic Boots - Black - Casual boots Our iconic heritage chukka gets a weatherized upgrade. A timeless boot made of rich, waterproof suede, it's lined in our UGG®plush upcycled wool blend and finished... more

$180.00

FREE shipping

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Saveli Chukka Boot

Saveli Chukka Boot

Men's Vince Camuto Saveli Chukka Boot - Green - Casual boots Rock the classic style in a comfier design with the Saveli chukka boot by Vince Camuto. This lace-up boot boasts the timeless ankle-length silhouette in a breathable fabric upper to make you... more

$104.99

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J. Crew Shoes | J.Crew Chukka Lace Up Tan Suede Desert Wedge Bootie Made In Italy Classic Chic 8 | Color: Tan | Size: 8

J. Crew Shoes | J.Crew Chukka Lace Up Tan Suede Desert Wedge Bootie Made In Italy Classic Chic 8 | Color: Tan | Size: 8

J.Crew Chukka Desert Wedge Boot. Genuine Suede Upper In Tan. Leather Lining. Adjustable Laces. Round Toe. Rounded Top Line. Crepe Rubber Wedge And Sole. Made In Italy. Classic Preppy Chic Neutral Light Academia Casual Office Dress Rugged Urban... more

$55.00

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Levi's Shoes | Levi's Mens Dean Wx Ul Rugged Casual Hiker Chukka Boot | Color: Brown | Size: 8

Levi's Shoes | Levi's Mens Dean Wx Ul Rugged Casual Hiker Chukka Boot | Color: Brown | Size: 8

These Levi's Dean Wx Ul Men's Chukka Boots Feature A Synthetic Vegan Leather Upper With A Classic Hiker Design. Boot Features 6 Hole Lace-Up Closure With Rugged Metal Eyelets Lightly Padded Collar For Extra Comfort Subtle Levi's Logo And Tab Details... more

$59.00

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