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

go to store
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

go to store
Best Seller
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

go to store
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

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

go to store
Men's Findley Chukka Boots by Propet in Black (Size 15 M)

Men's Findley Chukka Boots by Propet in Black (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 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
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

go to store
Taddeo Leather Chukka Boots

Taddeo Leather Chukka Boots

Men's Bruno Magli Taddeo Leather Chukka Boots - Black - Casual boots Bruno Magli "Taddeo" chukka boots in soft Italian calf leather 1.25 in / 30 mm stacked heel Round toe Laceup vamp Branded tongue and pull tab Boot shaft, approx. 6.0"H Rubber outsole... more

$375.00

FREE shipping

go to store
Bowery Leather Chukka Boots

Bowery Leather Chukka Boots

Men's Frye Bowery Leather Chukka Boots - Black - Casual boots Frye "Bowery" chukka boots featuring a recessed rubber lug forepart for added traction Goodyear welted construction Stacked heel Round toe Lace-up vamp Leather lining Debossed logo Leather... more

$328.00

FREE shipping

go to store
Side Zip Leather Chukka Boots

Side Zip Leather Chukka Boots

Men's Karl Lagerfeld Side Zip Leather Chukka Boots - Brown - Casual boots Karl Lagerfeld Paris chukka boots in box leather 1.25 in / 30 mm stacked heel Round toe Laceup vamp Side zip eases on and off Pulltab at backstay Embossed metal ring at backstay... more

$375.00

FREE shipping

go to store
Irish Setter Soft Paw Chukka Hiking Boots Leather Men's, Tan SKU - 375601

Irish Setter Soft Paw Chukka Hiking Boots Leather Men's, Tan SKU - 375601

The Irish Setter Soft Paw Chukka Leather Men's Hiking Boots are rugged and comfortably casual. The Soft Paw line features updated styling with new leathers and contrast stitching. The shoes also utilize a sole platform that combines ENERG material in... more

$174.95

go to store
Rocky Boots Dress Leather High Gloss Chukka - FQ00500-8EW100

Rocky Boots Dress Leather High Gloss Chukka - FQ00500-8EW100

Rocky Boots Dress Leather High Gloss Chukka - FQ00500-8EW100. It's A Footwear Experience Designed To Meet Daily Demands Of Your Job And Keep You Comfortable Long Past Clock-out. successful Work Requires A Durable Shoe. Goodyear Welt Construction And... more

$126.00

FREE shipping

go to store
Kenetrek Chukka Boots - Men's Brown 14 US Medium KE-0625-3 14.0MED

Kenetrek Chukka Boots - Men's Brown 14 US Medium KE-0625-3 14.0MED

Kenetrek Chukka Boots - Men's Brown 14 US Medium KE-0625-3 14.0MED. Made using an incredibly durable oil tanned leather material this pair of Men's Boots manufactured by the expert footwear manufacturers at Kenetrek will provide you with years of... more

$155.00

FREE shipping

go to store
Kenetrek Chukka Boots - Men's Brown 12 US Medium KE-0625-3 12.0MED

Kenetrek Chukka Boots - Men's Brown 12 US Medium KE-0625-3 12.0MED

Kenetrek Chukka Boots - Men's Brown 12 US Medium KE-0625-3 12.0MED. Made using an incredibly durable oil tanned leather material this pair of Men's Boots manufactured by the expert footwear manufacturers at Kenetrek will provide you with years of... more

$155.00

FREE shipping

go to store
TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 11.5

TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 11.5

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

go to store
TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 11

TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 11

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

go to store
TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 7

TOMS Men's Black Suede Travel Lite Moc Chukka Sneaker Shoes, Size 7

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

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
Men's Findley Chukka Boots by Propet in Tan (Size 9 M)

Men's Findley Chukka Boots by Propet in Tan (Size 9 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 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 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
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

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

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

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

go to store
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

go to store
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

go to store
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

go to store
Astor Sneaker-sole Leather Chukka Boots

Astor Sneaker-sole Leather Chukka Boots

Men's Frye Astor Sneaker-sole Leather Chukka Boots - Black 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
Bowery Leather Chukka Boots

Bowery Leather Chukka Boots

Men's Frye Bowery Leather Chukka Boots - Brown - Casual boots Frye "Bowery" chukka boots in distressed leather Stacked heel Round toe Lace-up vamp Goodyear welt Padded footbed Lining: Leather Made in Mexico. more

$328.00

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
Chandler Weatherproof Leather Chukka Boots

Chandler Weatherproof Leather Chukka Boots

Men's Allen Edmonds Chandler Weatherproof Leather Chukka Boots - Brown - Casual boots Allen Edmonds "Chandler" chukka boots in waterproof leather 360o bench welt construction for durability and stability 0.75 in / 20 mm stacked heel Round toe Lace-up... more

$495.00

FREE shipping

go to store
Leather Chukka Boots

Leather Chukka Boots

Men's Bruno Magli Leather Chukka Boots - Brown - Casual boots Bruno Magli "Alto" chukka boots in leather Flat heel Round moc toe Lace-up vamp Rubber sole Made in Italy. more

$279.00

FREE shipping

go to store
Crewson Crazy Horse Leather Chukka Boots

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

$150.00

FREE shipping

go to store
Astor Leather Chukka Boots

Astor Leather Chukka Boots

Men's Frye Astor Leather Chukka Boots - Brown - Casual boots Frye "Astor" chukka boots in premium soft leather feature a cushioned rubber sole Flat heel Round toe Lace-up vamp Comfort leather footbed Leather lining Debossed logo at side Imported Size... more

$228.00

FREE shipping

go to store
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

FREE shipping

go to store
Clarks(r) Wallabee Chukka Boot

Clarks(r) Wallabee Chukka Boot

Men's Clarks(r) Wallabee Chukka Boot - Black - Casual boots A classic crepe-rubber sole grounds a chunky leather chukka boot complete with a smartly stitched toe. more

$170.00

FREE shipping

go to store
Clarks(r) Wallabee Chukka Boot

Clarks(r) Wallabee Chukka Boot

Men's Clarks(r) Wallabee Chukka Boot - Natural - Casual boots A classic crepe-rubber sole grounds a chunky leather chukka boot complete with a smartly stitched toe. more

$170.00

FREE shipping

go to store
Clarks(r) Wallabee Chukka Boot

Clarks(r) Wallabee Chukka Boot

Men's Clarks(r) Wallabee Chukka Boot - Black - Casual boots A classic crepe-rubber sole grounds a chunky leather chukka boot complete with a smartly stitched toe. more

$170.00

FREE shipping

go to store

More information about Men's Shoes

Best prices on Leather 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.