Best Seller
Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (Size 14 M)

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

Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Wheat Nubuck (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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Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 11M 690774413337

Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 11M 690774413337

Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 11M 690774413337. ASTM F2413 Slip Resistant Electrical Hazard Protection Steel Toe truTECH Specifications for Rockport Prestige Point Chukka Steel Toe Work Boot - Mens: Manufacturer:... more

$167.00

FREE shipping

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Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 9.5M 690774413306

Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 9.5M 690774413306

Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 9.5M 690774413306. 5M more

$167.00

FREE shipping

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Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 8W 690774413405

Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 8W 690774413405

Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 8W 690774413405. ASTM F2413 Slip Resistant Electrical Hazard Protection Steel Toe truTECH Specifications for Rockport Prestige Point Chukka Steel Toe Work Boot - Mens: Manufacturer:... more

$167.00

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 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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TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 14

TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 14

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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Tilden Chukka Boot

Tilden Chukka Boot

Men's Stacy Adams Tilden Chukka Boot - Blue - Casual boots You can only up your dapper quo pairing the Tilden chukka boot by Stacy Adams with your outfit. This suede boot is highlighted with contrast welt and stitching details for a stylish look.... more

$79.99 $59.98

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Harken Chukka Boot

Harken Chukka Boot

Men's Steve Madden Harken Chukka Boot - Brown - Casual boots Boasting a classic look ready to pair with favorite formal or professional looks, the Harken chukka boot is sure to please. The contrast stitching makes for an eye-catching statement, while... more

$94.96

FREE shipping

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Neumel Leather Shoes Chukka Boots

Neumel Leather Shoes Chukka Boots

Women's Ugg Neumel Leather Shoes Chukka Boots - Black - Ankle boots Combining premium materials and effortless style, the Neumel is our iconic Heritage chukka. A timeless boot made of rich suede, it's lined in upcycled UGGplush wool and finished with a... more

$140.00 $97.99

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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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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 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
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

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 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 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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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
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 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
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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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

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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

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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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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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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

go to store
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

go to store
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

go to store
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

go to store
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

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