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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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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Best Seller
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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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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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 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 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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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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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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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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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 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 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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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 5.5 Wide 690774227507

Reebok Postal Express Chukka Boots - Men's Black 5.5 Wide 690774227507

Reebok Postal Express Chukka Boots - Men's Black 5.5 Wide 690774227507. 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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Astor Sneaker-sole Leather Chukka Boots

Astor Sneaker-sole Leather Chukka Boots

Men's Frye Astor Sneaker-sole Leather Chukka Boots - Brown Frye "Astor" leather chukka boots feature a rubber sneaker sole Flat heel Round toe Leather lace-up vamp Stamped logo on the side Lining: Leather Imported. more

$228.00

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 $318.40

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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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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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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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

go to store
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
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® 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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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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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 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

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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

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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 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 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 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

go to store
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

go to store
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

go to store
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

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

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