Best Seller
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

go to store
Wide Width Men's Warren Chukka Boot by Deer Stags in Black (Size 10 W)

Wide Width Men's 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 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 $74.99

go to store
Best Seller
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 $74.99

go to store
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 $74.99

go to store
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 $124.99

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 $124.99

go to store
Lace-Up Chukka Boot

Lace-Up Chukka Boot

Designed with a lace-up closure, this boot shows off a chukka-inspired silhouette and our J-class icon embossed at the tongue. more

$70.00 $39.99

go to store
Lace-Up Chukka Boot

Lace-Up Chukka Boot

Designed with a lace-up closure, this boot shows off a chukka-inspired silhouette and our J-class icon embossed at the tongue. more

$70.00 $39.99

go to store
Lace-Up Chukka Boot

Lace-Up Chukka Boot

Designed with a lace-up closure, this boot shows off a chukka-inspired silhouette and our J-class icon embossed at the tongue. more

$70.00 $39.99

go to store
Men's Warren Chukka Boot by Deer Stags in Black (Size 12 M)

Men's 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 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 $74.99

go to store
Men's Warren Chukka Boot by Deer Stags in Wheat Nubuck (Size 12 M)

Men's Warren Chukka Boot by Deer Stags in Wheat Nubuck (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 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 $74.99

go to store
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 $74.99

go to store
Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 13M 690774413368

Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 13M 690774413368

Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 13M 690774413368. 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

go to store
Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 7M 690774413252

Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 7M 690774413252

Rockport Prestige Point Chukka Steel Toe Work Boot - Men's Brown 7M 690774413252. 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

go to store
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

go to store
TOMS Men's Brown Water Resistant Topaz Navi Boots, Size 11

TOMS Men's Brown Water Resistant Topaz Navi Boots, Size 11

For dressing up or buckling down, the Navi is your trusty lace-up chukka boot durable enough to withstand whatever life-or the weather-throws your way. | Water-resistant leather upper Welted, lightweight injection outsole with serrated tread for... more

$119.95

FREE shipping

go to store
TOMS Men's Brown Water Resistant Topaz Navi Boots, Size 14

TOMS Men's Brown Water Resistant Topaz Navi Boots, Size 14

For dressing up or buckling down, the Navi is your trusty lace-up chukka boot durable enough to withstand whatever life-or the weather-throws your way. | Water-resistant leather upper Welted, lightweight injection outsole with serrated tread for... more

$119.95

FREE shipping

go to store
TOMS Men's Brown Water Resistant Topaz Navi Boots, Size 10.5

TOMS Men's Brown Water Resistant Topaz Navi Boots, Size 10.5

For dressing up or buckling down, the Navi is your trusty lace-up chukka boot durable enough to withstand whatever life-or the weather-throws your way. | Water-resistant leather upper Welted, lightweight injection outsole with serrated tread for... more

$119.95

FREE shipping

go to store
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

go to store
Livingston Chukka Boot

Livingston Chukka Boot

Men's Taft Livingston Chukka Boot - Black - Casual boots Keep your look distinguished with the Livingston chukka boot from Taft. A wingtip toe with brogue accentuation creates a tasteful look to the leather and wool boot, made cozy with a cushioned... more

$294.99

FREE shipping

go to store
Vandick Chukka Boot

Vandick Chukka Boot

Men's Sandro Moscoloni Vandick Chukka Boot - Blue - Casual boots The Vandick chukka boot from Sandro Moscoloni proves a versatile must-have with a classic design to finish off favorite fits. This leather pair's cushioned footbed adds a comfortable... more

$198.99

FREE shipping

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
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 Warren Chukka Boot by Deer Stags in Black (Size 14 M)

Men's 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 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 $74.99

go to store
Wide Width Men's Warren Chukka Boot by Deer Stags in Wheat Nubuck (Size 10 W)

Wide Width Men's 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 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 $74.99

go to store
Men's Warren Chukka Boot by Deer Stags in Black (Size 12 M)

Men's 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 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 $74.99

go to store
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

go to store
Wide Width Men's Warren Chukka Boot by Deer Stags in Black (Size 13 W)

Wide Width Men's 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 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 $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

go to store
Wide Width Men's Warren Chukka Boot by Deer Stags in Black (Size 12 W)

Wide Width Men's 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 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 $74.99

go to store
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

go to store
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

go to store
Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 13 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Bomber Brown (Size 13 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 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

go to store
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 Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 14 M)

Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 14 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 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

go to store
Men's Warren Chukka Boot by Deer Stags in Black (Size 13 M)

Men's 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 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 $74.99

go to store
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

go to store
Wide Width Men's Warren Chukka Boot by Deer Stags in Wheat Nubuck (Size 13 W)

Wide Width Men's Warren Chukka Boot by Deer Stags in Wheat Nubuck (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 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 $74.99

go to store

More information about Men's Shoes

Best prices on Chukka boots in Men's Shoes online. Visit Bizrate to find the best deals on top brands. Read reviews on Clothing & Accessories merchants and buy with confidence.