Men's Shoes › chukka boots

Fremont Chukka Boot

Men's Gordon Rush Fremont Chukka Boot - Black - Casual boots A supple suede upper and plain toe distinguish a refined chukka boot set on a well-cushioned footbed and lightweight sole for long-lasting comfort. more

Jimmy Chukka Boot

Men's Vance Co. Jimmy Chukka Boot - Blue - Casual boots Want to look impressive around the clock? Then choose the Jimmy chukka boot by Vance Co. This lace-up sneaker ensures above-par comfort levels with its Tru Comfort foam insole. EVA sole stays... more

Booker Chukka Boot

Men's Thomas & Vine Booker Chukka Boot - Black - Casual boots The Booker chukka boot by Thomas & Vine is an all star that goes well with both casual and formal wardrobe. Set on a lightweight EVA sole, this boot features an 8mm Comfort FoamTM insole and... more

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

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Medium DDB0248-11-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 11 Medium DDB0248-11-M. 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

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Medium DDB0248-13-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 13 Medium DDB0248-13-M. 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

Danner Pilgrim Chukka 4.5" Boots Leather Men's, Timberwolf SKU - 745519

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

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

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 12 Wide DDB0248-12-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 12 Wide DDB0248-12-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

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

Columbia Shoes | Men's Columbia Davenport Chukka Boot | Color: Brown/Tan | Size: 7.5

Men'scolumbia Davenport Chukka Nubuck Leather Boot Very Good Used Condition. These Were Worn With Different Inserts So The Original Columbia Inserts, Which Will Be With These Boots, Are New Nubuck Upper Smooth, Composite Lining Decorative Metal Eyelet... more

Carhartt Shoes | Carhartt Cmx4023 Lightweight Wedge Moc Toe Oil Tanned Chukka Boots | 10.5 W | Color: Brown/Tan | Size: 10.5

Carhartt Cmx4023 Lightweight Wedge Moc Toe Oil Tanned Chukka Boots | 10.5 W Men's Lightweight Work Boots For Everyday Wear. Leather Durability And Sneaker Comfort. These Lightweight Boots Blend A Stitched-Leather Upper And Cushioned Sneaker-Like... more

Carhartt Shoes | Carhartt Lightweight 4-Inch Wedge Chukka Boots | Color: Brown | Size: Various

Carhartt Lightweight 4-Inch Wedge Chukka Boots. Soft Toe. Brown. Fastdry Lining Wicks Sweat. Model No, Fx4023-M more

Thomas and Vine Thomas & Vine Keegan Plain Toe Chukka Boot - Brown - 13

Casual enough for every day, suave enough for dinner, the Keegan by Thomas & Vine. This handsome round-toe chukka boot features genuine leather or suede uppers and a two-eye lace-up closure with a second pair of interchangeable laces. An 8 mm Tru... more

Vance Co. Shoes Arturo Plain Toe Chukka Boot - Brown - 13

Introducing Arturo by Vance Co., the ankle boot that offers a classic look with modern comfort. Made with vegan leather and featuring an almond-toe and lace-up design, Arturo adds a touch of sophistication to any outfit. The lightweight EVA outsole, 12... more

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Black - 8

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

Crewson Crazy Horse Leather Chukka Boots

Men's Dr. Martens Crewson Crazy Horse Leather Chukka Boots - Brown - Casual boots Taking cues from our 6-eye 101 silhouette, the Crewson Chukka boot unites our heritage markings in one of our lightest ever constructions. Engineered with functionality... more

Wythe Waterproof Chukka Boot

Men's GREATS Wythe Waterproof Chukka Boot - Blue - Casual boots A toothy sneaker-inspired sole adds a sporty touch to a lightweight chukka boot crafted with seam-sealed waterproof construction. more

Booker Chukka Boot

Men's Thomas & Vine Booker Chukka Boot - Brown - Casual boots The Booker chukka boot by Thomas & Vine is an all star that goes well with both casual and formal wardrobe. Set on a lightweight EVA sole, this boot features an 8mm Comfort FoamTM insole and... more

Davis Square Chukka Boot

Men's Timberland Davis Square Chukka Boot - Brown - Casual boots Elevate your casual wardrobe with the Davis Square chukka boot from Timberland. The plush trim on the collar lend a cozy touch, while the Defender Repellent Systems treatment deters... more

Keegan Chukka Boot

Men's Thomas & Vine Keegan Chukka Boot - Black - Casual boots The Keegan chukka boot by Thomas & Vine is your go-to footwear for the in-between occasions. Outfitted with a sporty outsole, this boot is topped with genuine leather upper and includes a... more

Wythe Waterproof Chukka Boot

Men's GREATS Wythe Waterproof Chukka Boot - White - Casual boots A toothy sneaker-inspired sole adds a sporty touch to a lightweight chukka boot crafted with seam-sealed waterproof construction. more

Distillery Waterproof Faux Shearling Lined Chukka Boot

Men's Baffin Distillery Waterproof Faux Shearling Lined Chukka Boot - Brown - Casual boots Keep your look on point as you brave icy sidewalks and slushy city streets with confidence in this waterproof leather boot lined with plush faux shearling. A... more

Fremont Chukka Boot

Men's Gordon Rush Fremont Chukka Boot - Brown - Casual boots A supple suede upper and plain toe distinguish a refined chukka boot set on a well-cushioned footbed and lightweight sole for long-lasting comfort. more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Medium DDB0248-105-M

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Medium DDB0248-105-M. 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... more

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Wide DDB0248-105-W

Durango Boot Red Dirt Rebel Square-Toe 5 inch Chukka - Men's Bark Brown 10.5 Wide DDB0248-105-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... more

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

Neumel High Moc Weather Boot

Men's Ugg Neumel High Moc Weather Boot - Brown - Casual boots Adapting the Neumel with distinctive moc stitching for a refined finish, this high-top take on our timeless chukka is cold-weather rated to -20C with seam-sealed construction and waterproof... more

® 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

® Neumel Moc Suede Classic Boots

Men's Ugg ® Neumel Moc Suede Classic Boots - Black - Casual boots Adapting our timeless chukka silhouette with moc-style stitching for a refined finish, the Neumel Moc combines premium materials and effortless style. Made of rich suede, it's lined in... more

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK11W

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK11W. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For... more

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK13W

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK13W. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For... more

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK115W

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK115W. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For... more

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK95M

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK95M. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For... more

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK9W

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK9W. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For The... more

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK75M

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK75M. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For... more

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK95W

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK95W. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For... more

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK11M

Rocky Boots Tmc Postal-approved Public Service Chukka Boots - FQ0005005BK11M. Thoughtfully Constructed With Solid Black Full-grain Leather That Is Both Water-resistant And Polishable The Excellent Appearance Of This Work Shoe Is Easy To Maintain For... more