Best Seller
Women's Oscar Bootie by Eastland in Grey (Size 13 D)

Women's Oscar Bootie by Eastland in Grey (Size 13 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

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Women's Oscar Bootie by Eastland in Grey (Size 11 1/2 D)

Women's Oscar Bootie by Eastland in Grey (Size 11 1/2 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

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Best Seller
Women's Oscar Bootie by Eastland in Grey (Size 11 D)

Women's Oscar Bootie by Eastland in Grey (Size 11 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store
Women's Oscar Bootie by Eastland in Grey (Size 11 1/2 D)

Women's Oscar Bootie by Eastland in Grey (Size 11 1/2 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

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Women's Oscar Bootie by Eastland in Grey (Size 9 1/2 D)

Women's Oscar Bootie by Eastland in Grey (Size 9 1/2 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

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Women's Oscar Bootie by Eastland in Grey (Size 9 D)

Women's Oscar Bootie by Eastland in Grey (Size 9 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

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Women's Oscar Bootie by Eastland in Grey (Size 9 1/2 D)

Women's Oscar Bootie by Eastland in Grey (Size 9 1/2 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

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Women's Oscar Bootie by Eastland in Grey (Size 13 D)

Women's Oscar Bootie by Eastland in Grey (Size 13 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

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Women's Oscar Bootie by Eastland in Grey (Size 11 D)

Women's Oscar Bootie by Eastland in Grey (Size 11 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

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Wide Width Men's Findley Chukka Boots by Propet in Black (Size 9 W)

Wide Width Men's Findley Chukka Boots by Propet in Black (Size 9 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 Black (Size 10 1/2 M)

Men's Findley Chukka Boots by Propet in Black (Size 10 1/2 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 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... more

$110.00

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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 $124.99

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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 $124.99

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

Wide Width Men's 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 Warren Chukka Boot by Deer Stags® is a reliable shoe to keep you comfortable during a night out and special occasions. Lace-up... more

$124.99 $86.99

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

Men's 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 Warren Chukka Boot by Deer Stags® is a reliable shoe to keep you comfortable during a night out and special occasions. Lace-up... more

$124.99 $86.99

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Wide Width Men's Warren Chukka Boot by Deer Stags in Black (Size 9 W)

Wide Width Men's 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 Warren Chukka Boot by Deer Stags® is a reliable shoe to keep you comfortable during a night out and special occasions. Lace-up... more

$124.99 $86.99

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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 $124.99

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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 12W 690774413481

Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 12W 690774413481

Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 12W 690774413481. 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 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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Men's Trvl Lite Forrest Dark Leather Ankle Boot | Brown | Size 7 | TOMS Official Site - Shoes, Accessories, & Apparel

Men's Trvl Lite Forrest Dark Leather Ankle Boot | Brown | Size 7 | TOMS Official Site - Shoes, Accessories, & Apparel

Trek forward in the Forrest boot, made with a low-profile Chukka silhouette and waxed brown canvas and leather. Fitted with TRVL LITE technology for superior comfort. Wear with jeans for a classic look that never goes out of style. Leather and... more

$129.95

FREE shipping

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Men's Trvl Lite Forrest Dark Leather Ankle Boot | Brown | Size 7.5 | TOMS Official Site - Shoes, Accessories, & Apparel

Men's Trvl Lite Forrest Dark Leather Ankle Boot | Brown | Size 7.5 | TOMS Official Site - Shoes, Accessories, & Apparel

Trek forward in the Forrest boot, made with a low-profile Chukka silhouette and waxed brown canvas and leather. Fitted with TRVL LITE technology for superior comfort. Wear with jeans for a classic look that never goes out of style. Leather and... more

$129.95

FREE shipping

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Men's Trvl Lite Forrest Dark Leather Ankle Boot | Brown | Size 8.5 | TOMS Official Site - Shoes, Accessories, & Apparel

Men's Trvl Lite Forrest Dark Leather Ankle Boot | Brown | Size 8.5 | TOMS Official Site - Shoes, Accessories, & Apparel

Trek forward in the Forrest boot, made with a low-profile Chukka silhouette and waxed brown canvas and leather. Fitted with TRVL LITE technology for superior comfort. Wear with jeans for a classic look that never goes out of style. Leather and... more

$129.95

FREE shipping

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Women's Oscar Bootie by Eastland in Grey (Size 10 1/2 D)

Women's Oscar Bootie by Eastland in Grey (Size 10 1/2 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store
Women's Oscar Bootie by Eastland in Grey (Size 9 D)

Women's Oscar Bootie by Eastland in Grey (Size 9 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store
Women's Oscar Bootie by Eastland in Grey (Size 9 1/2 D)

Women's Oscar Bootie by Eastland in Grey (Size 9 1/2 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store
Women's Oscar Bootie by Eastland in Grey (Size 11 1/2 D)

Women's Oscar Bootie by Eastland in Grey (Size 11 1/2 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store
Women's Oscar Bootie by Eastland in Grey (Size 9 D)

Women's Oscar Bootie by Eastland in Grey (Size 9 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store
Women's Oscar Bootie by Eastland in Grey (Size 8 D)

Women's Oscar Bootie by Eastland in Grey (Size 8 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

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® Neumel Moc Suede Classic Boots

® Neumel Moc Suede Classic Boots

Men's Ugg ® Neumel Moc Suede Classic Boots - Brown - Casual boots Adapting our timeless chukka silhouette with moc-style stitching for a refined finish, the Neumel Moc effortlessly combines premium materials and style. Crafted from rich suede, this... more

$150.00

FREE shipping

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® Infants' Neumel Leather Shoes Chukka Boots

® Infants' Neumel Leather Shoes Chukka Boots

Women's Ugg ® Infants' Neumel Leather Shoes Chukka Boots - Black Allow your little ones to face the elements fashionably as well. Crafted from smooth suede and featuring a wool lining, the Baby Neumel comes with a hook-and-loop closure for... more

$55.00

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Suede Lace-up Chukka Boots

Suede Lace-up Chukka Boots

Men's Tod's Suede Lace-up Chukka Boots - Blue - Casual boots Tods mens boots. Polacco gomma leggero tf series. Shoe style: chukka boots. Vamp style: lace-up. Upper material: suede. Solematerial: rubber. Tods mens suede lace-up chukka boots. Lace-up... more

$445.00 $249.97

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Women's Oscar Bootie by Eastland in Grey (Size 8 D)

Women's Oscar Bootie by Eastland in Grey (Size 8 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store
Women's Oscar Bootie by Eastland in Grey (Size 10 1/2 D)

Women's Oscar Bootie by Eastland in Grey (Size 10 1/2 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store
Women's Oscar Bootie by Eastland in Grey (Size 9 D)

Women's Oscar Bootie by Eastland in Grey (Size 9 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store
Women's Oscar Bootie by Eastland in Grey (Size 10 1/2 D)

Women's Oscar Bootie by Eastland in Grey (Size 10 1/2 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store
Women's Oscar Bootie by Eastland in Grey (Size 8 D)

Women's Oscar Bootie by Eastland in Grey (Size 8 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store
Women's Oscar Bootie by Eastland in Grey (Size 8 D)

Women's Oscar Bootie by Eastland in Grey (Size 8 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store
Women's Oscar Bootie by Eastland in Grey (Size 10 1/2 D)

Women's Oscar Bootie by Eastland in Grey (Size 10 1/2 D)

This classic chukka boot gets a modern, sporty redesign in this comfortable, go-to style. Leather upper with a detailed stitched mock toe design. Comfort leather sock lining and insole supports and conforms to the curves of your foot. Rubber outsole... more

$216.99

go to store

More information about Men's Shoes

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