Best Seller
Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 9 D

Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 9 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 $186.00

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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 $186.00

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Best Seller
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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Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 13 D

Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 13 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 $186.00

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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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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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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

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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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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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Reebok Postal Express Chukka Boots - Men's Black 4 Wide 690774227477

Reebok Postal Express Chukka Boots - Men's Black 4 Wide 690774227477

Reebok Postal Express Chukka Boots - Men's Black 4 Wide 690774227477. 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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Pendleton Chukka Boots

Pendleton Chukka Boots

Men's Maison Margiela Pendleton Chukka Boots - Brown - Casual boots 100% Wool, 100% Calf Leather, 100% Rubber. Made in Italy. more

$1,031.56 $577.08

FREE shipping

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Excursionist Suede Chukka Boots

Excursionist Suede Chukka Boots

Men's Peter Millar Excursionist Suede Chukka Boots - Gray - Casual boots Peter Millar "Excursionist" chukka boots in waterresistant suede with sneakerlike comfort Flat heel Round toe Laceless vamp Slipon style Leather/Rubber outsole Spot clean Made in... more

$295.00

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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Irish Setter Soft Paw Chukka Hiking Boots Leather Men's, Tan SKU - 816107

Irish Setter Soft Paw Chukka Hiking Boots Leather Men's, Tan SKU - 816107

The Irish Setter Soft Paw Chukka Leather Men's Hiking Boots are rugged and comfortably casual. The Soft Paw line features updated styling with new leathers and contrast stitching. The shoes also utilize a sole platform that combines ENERG material in... more

$174.95

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Irish Setter Soft Paw Chukka Hiking Boots Leather Men's, Tan SKU - 375601

Irish Setter Soft Paw Chukka Hiking Boots Leather Men's, Tan SKU - 375601

The Irish Setter Soft Paw Chukka Leather Men's Hiking Boots are rugged and comfortably casual. The Soft Paw line features updated styling with new leathers and contrast stitching. The shoes also utilize a sole platform that combines ENERG material in... more

$174.95

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TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 12

TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 12

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 8.5

TOMS Men's Brown Waxy Suede Travel Lite Moc Chukka Sneaker Shoes, Size 8.5

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 8.5

TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 8.5

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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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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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 13 Wide DDB0248-13-W

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

$141.50

FREE shipping

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Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 11 D

Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 11 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 $186.00

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Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 12 D

Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 12 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 $186.00

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Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 11½ D

Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 11½ 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 $186.00

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Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 10½ D

Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 10½ 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 $186.00

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Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 8½ D

Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 8½ 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 $186.00

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

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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

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
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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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
Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 8 D

Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 8 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 $186.00

go to store
Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 9½ D

Brooks Brothers Men's Hayden Camp Chukka Shoes | Tan | Size 9½ 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 $186.00

go to store
Wide Width Men's Findley Chukka Boots by Propet in Tan (Size 15 W)

Wide Width Men's Findley Chukka Boots by Propet in Tan (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

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

Men's Findley Chukka Boots by Propet in Tan (Size 15 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 15 M)

Men's Findley Chukka Boots by Propet in Black (Size 15 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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