Best Seller
Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Black (Size 12 M)

Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Black (Size 12 M)

These Deer Stags® Bangor Chukka Boots get an upgrade with contrast stitching and a crepe-like grippy bottom, great for formal and casual situations. Soft fabric linings help to wick moisture and keep your feet cool. Faux leatherContrast... more

$100.99 $69.99

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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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Best Seller
Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Black (Size 15 M)

Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Black (Size 15 M)

These Deer Stags® Bangor Chukka Boots get an upgrade with contrast stitching and a crepe-like grippy bottom, great for formal and casual situations. Soft fabric linings help to wick moisture and keep your feet cool. Faux leatherContrast... more

$100.99 $69.99

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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 12 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 12 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Danner Pilgrim Chukka 4.5" Boots Leather Men's, Bracken SKU - 310650

Danner Pilgrim Chukka 4.5" Boots Leather Men's, Bracken SKU - 310650

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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Brooks Brothers Men's 1818 Footwear Suede Chukka Boots | Beige | Size 7 D

Brooks Brothers Men's 1818 Footwear Suede Chukka Boots | Beige | Size 7 D

The 1818 Footwear Collection combines Italian craftsmanship, the finest materials and timeless designs to produce versatile, comfortable shoes that form a solid foundation for the polished wardrobe. These essential chukka boots are crafted from Italian... more

$298.00 $119.99

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Brooks Brothers Men's 1818 Footwear Suede Chukka Boots | Beige | Size 7½ D

Brooks Brothers Men's 1818 Footwear Suede Chukka Boots | Beige | Size 7½ D

The 1818 Footwear Collection combines Italian craftsmanship, the finest materials and timeless designs to produce versatile, comfortable shoes that form a solid foundation for the polished wardrobe. These essential chukka boots are crafted from Italian... more

$298.00 $119.99

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Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 10 D

Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 10 D

The ultimate camp boot is here with a soft suede upper, full leather lining, and rubber camp sole that keeps you dry while adding long-term durability. Our leather footbed houses a memory foam pad that ensures comfort during all-terrain wear. 100%... more

$248.00

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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 11 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 11 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 12 M)

Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 12 M)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 10 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 10 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Reebok Postal Express Chukka Boots - Men's Wide Black 14 690774475113

Reebok Postal Express Chukka Boots - Men's Wide Black 14 690774475113

Reebok Postal Express Chukka Boots - Men's Wide Black 14 690774475113. Specifications for Reebok Postal Express Chukka Boots - Men's: Manufacturer: Reebok Gender: Male Footwear Type: Boots Toe Type: Soft Color: Black Footwear Upper Fabric/Material:... more

$229.00

FREE shipping

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Reebok Postal Express Chukka Boots - Men's Black 5 Medium 690774227453

Reebok Postal Express Chukka Boots - Men's Black 5 Medium 690774227453

Reebok Postal Express Chukka Boots - Men's Black 5 Medium 690774227453. Specifications for Reebok Postal Express Chukka Boots - Men's: Manufacturer: Reebok Gender: Male Footwear Type: Boots Toe Type: Soft Color: Black Footwear Upper Fabric/Material:... more

$229.00

FREE shipping

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Reebok Postal Express Chukka Boots - Men's Black 4.5 Medium 690774227446

Reebok Postal Express Chukka Boots - Men's Black 4.5 Medium 690774227446

Reebok Postal Express Chukka Boots - Men's Black 4.5 Medium 690774227446. Specifications for Reebok Postal Express Chukka Boots - Men's: Manufacturer: Reebok Gender: Male Footwear Type: Boots Toe Type: Soft Color: Black Footwear Upper Fabric/Material:... more

$229.00

FREE shipping

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Papakū 'ili Waterproof Chukka Boot

Papakū 'ili Waterproof Chukka Boot

Men's Olukai Papakū 'ili Waterproof Chukka Boot - Black - Casual boots This waterproof-leather chukka boot will be a cold-weather go-to thanks to its plush quilted lining and a Wet Grip rubber sole providing superior traction. more

$160.00

FREE shipping

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Chandler Chukka Boot

Chandler Chukka Boot

Men's Allen Edmonds Chandler Chukka Boot - Brown - Casual boots Premium, finely napped suede elevates a classic chukka boot handcrafted with a comfortable cork insole, durable bench welt and rubber grip sole. 360o welt construction for durability and... more

$495.00

FREE shipping

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Theo Chukka Boot

Theo Chukka Boot

Men's Thomas & Vine Theo Chukka Boot - Black - 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

$49.99

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Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Red Wood (Size 14 M)

Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Red Wood (Size 14 M)

These Deer Stags® Bangor Chukka Boots get an upgrade with contrast stitching and a crepe-like grippy bottom, great for formal and casual situations. Soft fabric linings help to wick moisture and keep your feet cool. Faux leatherContrast... more

$100.99 $69.99

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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 13 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 13 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Red Wood (Size 13 M)

Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Red Wood (Size 13 M)

These Deer Stags® Bangor Chukka Boots get an upgrade with contrast stitching and a crepe-like grippy bottom, great for formal and casual situations. Soft fabric linings help to wick moisture and keep your feet cool. Faux leatherContrast... more

$100.99 $69.99

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Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Red Wood (Size 16 M)

Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Red Wood (Size 16 M)

These Deer Stags® Bangor Chukka Boots get an upgrade with contrast stitching and a crepe-like grippy bottom, great for formal and casual situations. Soft fabric linings help to wick moisture and keep your feet cool. Faux leatherContrast... more

$100.99 $69.99

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Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Black (Size 16 M)

Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Black (Size 16 M)

These Deer Stags® Bangor Chukka Boots get an upgrade with contrast stitching and a crepe-like grippy bottom, great for formal and casual situations. Soft fabric linings help to wick moisture and keep your feet cool. Faux leatherContrast... more

$100.99 $69.99

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Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Red Wood (Size 12 M)

Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Red Wood (Size 12 M)

These Deer Stags® Bangor Chukka Boots get an upgrade with contrast stitching and a crepe-like grippy bottom, great for formal and casual situations. Soft fabric linings help to wick moisture and keep your feet cool. Faux leatherContrast... more

$100.99 $69.99

go to store
Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Black (Size 14 M)

Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Black (Size 14 M)

These Deer Stags® Bangor Chukka Boots get an upgrade with contrast stitching and a crepe-like grippy bottom, great for formal and casual situations. Soft fabric linings help to wick moisture and keep your feet cool. Faux leatherContrast... more

$100.99 $69.99

go to store
Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Black (Size 13 M)

Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Black (Size 13 M)

These Deer Stags® Bangor Chukka Boots get an upgrade with contrast stitching and a crepe-like grippy bottom, great for formal and casual situations. Soft fabric linings help to wick moisture and keep your feet cool. Faux leatherContrast... more

$100.99 $69.99

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Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 9 1/2 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 9 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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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 14 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 14 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 10 1/2 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 10 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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Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 9 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 9 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 Propet Findley Men'S Chukka Boots by Propet in Desert Camel (Size 12 M)

Men's Propet Findley Men'S Chukka Boots by Propet in Desert Camel (Size 12 M)

Plain toe suede 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. Removable Footbed.FABRIC: SuedeFIT: True to... more

$109.99

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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 9 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 9 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

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Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 9 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 9 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 10 1/2 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 10 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

go to store
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

go to store
Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 10 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 10 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

go to store
Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 13 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 13 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

go to store
Men's Propet Findley Men'S Chukka Boots by Propet in Desert Camel (Size 15 M)

Men's Propet Findley Men'S Chukka Boots by Propet in Desert Camel (Size 15 M)

Plain toe suede 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. Removable Footbed.FABRIC: SuedeFIT: True to... more

$109.99

go to store
Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 14 M)

Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 14 M)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

go to store
Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 11 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 11 W)

They look like dress boots yet have the comfort of your favorite pair of sneakers! Made with a memory foam insole, the Deer Stags® Warren Chukka Boot is the reliable shoe to keep you comfortable during a night out and special occasion. Synthetic... more

$124.99 $74.99

go to store
Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 11 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 11 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

go to store

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