Best Seller
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

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

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (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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Best Seller
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

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

Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 13 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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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 Black (Size 14 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (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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TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 7

TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 7

A suede spin on the Desert Boot. The coffee undertones and fully-lined canvas paired with our iconic OrthoLite® comfort will keep you looking good while feeling good. Wear TOMS. WEAR GOOD. | Suede upper. TOMS leather products support responsible... more

$119.95 $99.99

FREE shipping

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TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 10

TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 10

A suede spin on the Desert Boot. The coffee undertones and fully-lined canvas paired with our iconic OrthoLite® comfort will keep you looking good while feeling good. Wear TOMS. WEAR GOOD. | Suede upper. TOMS leather products support responsible... more

$119.95 $99.99

FREE shipping

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TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 10.5

TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 10.5

A suede spin on the Desert Boot. Fully-lined canvas paired with our iconic OrthoLite® comfort will keep you looking good while feeling good. Wear TOMS. WEAR GOOD. | Suede upper. TOMS leather products support responsible manufacturing via the Leather... more

$119.95 $99.99

FREE shipping

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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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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 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 6.5 Wide 690774213777

Reebok Postal Express Chukka Boots - Men's Black 6.5 Wide 690774213777

Reebok Postal Express Chukka Boots - Men's Black 6.5 Wide 690774213777. 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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Varick Leather Chukka Boot

Varick Leather Chukka Boot

Men's John Varvatos Varick Leather Chukka Boot - Black - Casual boots A smooth leather construction enhances the dapper look of this chukka boot styled with a fabric heel loop for easy entry. Leather upper, lining and sole Made in Portugal. more

$398.00

FREE shipping

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Taddeo Suede Chukka Boots

Taddeo Suede Chukka Boots

Men's Bruno Magli Taddeo Suede Chukka Boots - Brown - Casual boots Bruno Magli "Taddeo" chukka boots in soft Italian suede 1.25 in / 30 mm stacked heel Round toe Laceup vamp Branded tongue and pull tab Boot shaft, approx. 6.0"H Rubber outsole Item... more

$375.00

FREE shipping

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Colton Chukka Boot

Colton Chukka Boot

Men's Blake McKay Colton Chukka Boot - Brown - Casual boots Contrast stitching highlights the classic silhouette of a smooth leather chukka boot grounded by a cushioned, arch-supporting OrthoLite® footbed. more

$165.00

FREE shipping

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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 Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 12 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 12 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 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 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 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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Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 11 1/2 M)

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

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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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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

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

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

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

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

go to store
Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 9 W)

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

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

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

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

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

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

go to store
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 Tan (Size 13 M)

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

Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (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
Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 12 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 12 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 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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