Men's Shoes › Leather › chukka boots

Maxwell Chukka Boot

Men's Stacy Adams Maxwell Chukka Boot - Brown - Casual boots The Maxwell chukka boot by Stacy Adams can look absolutely slick, be it tuxedos or distressed jeans. Smooth burnished leather, RedZone insole with molded heel and rubber sole make this... more

Kenetrek Chukka Boots - Men's Brown 6 US Medium KE-0625-3 06.0MED

Kenetrek Chukka Boots - Men's Brown 6 US Medium KE-0625-3 06.0MED. 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

Reebok Postal Express Chukka Boots - Men's Black 4.5 Medium 690774227446

Reebok Postal Express Chukka Boots - Men's Black 4.5 Medium 690774227446. Specifications for Reebok Postal Express Chukka Boots - Men's: Manufacturer: Reebok Gender: Male Footwear Type: Boots Toe Type: Soft Color: Black Footwear Upper Fabric/Material:... more

Bowery Chukka Boots

Men's Frye Bowery 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

Thorne Chukka Boot

Men's Crosby Square Thorne Chukka Boot - Brown - Casual boots A rear pull-tab lends easy entry to a supple suede chukka boot grounded by a cushioned footbed and flexible crepe sole. Lace-up style Cushioned footbed with arch support Leather upper and... more

Maple Grove Chukka Boot

Men's Timberland Maple Grove Chukka Boot - White - Casual boots Sporty yet refined, this leather chukka boot is one you can feel good about, with a lining made partially from post-consumer plastic bottles. more

Everyday Chukka Boot

Men's Nisolo Everyday Chukka Boot - Blue - Casual boots Meeting daily errands or heading to occasions can look stylish in the NISOLO Everyday chukka boot. The sustainable ankle boot features a 5-layer memory foam antimicrobial insole offering a fresh... more

Keegan Chukka Boot

Men's Thomas & Vine Keegan Chukka Boot - Brown - 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

Shacre Chukka Boot

Men's Clarks Shacre Chukka Boot - Brown - Casual boots Finish off chilly weather looks with the classic vibe of the Shacre chukka boot from Clarks. The leather construction proves a lasting highlight, while the Extreme Comfort insole pads your steps... more

Detroit Chukka Boot

Men's Hush Puppies Detroit Chukka Boot - Brown - Casual boots Own your weekend look with the Detroit chukka boot by Hush Puppies. It features water-resistant WorryFree® leather upper, recycled sock lining and supportive Bounce® and Memory foam footbed... more

Alto Suede Chukka Boot

Men's AllSaints Alto Suede Chukka Boot - Brown - Casual boots Contrast stitching and traditional three-hole lacing further the relaxed, wear-everywhere appeal of a suede chukka boot set on a sole of cushy crepe rubber. Lace-up style Leather upper and... more

Navi Water Resistant Chukka Boot

Men's TOMS Navi Water Resistant Chukka Boot - Black - Casual boots Perfect for both casual and active wear, this chukka boot features a water-resistant leather upper and a cushioned insole. more

Larrado Weatherproof Chukka Boot

Men's Ron White Larrado Weatherproof Chukka Boot - Brown - Casual boots A leather upper and soft flannel collar add modern elements to a sophisticated chukka boot grounded by a cushioned footbed and durable lug sole. Multilayered, PORON®-cushioned... more

Alder Chukka Boot

Men's Blake McKay Alder Chukka Boot - Black - Casual boots Crafted from rich, breathable leather and durable rubber, this flexible chukka boot is a wardrobe workhorse that's sure to be on heavy rotation all year long. The antimicrobial insole means a... more

Bilton Chukka Boot

Men's AllSaints Bilton Chukka Boot - Brown - Casual boots A classic crepe rubber sole lends a surefooted stride in this derby-inspired chukka boot crafted from supple, velvety suede. Lace-up style Leather upper and lining/rubber sole Made in Portugal. more

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

Detroit Chukka Boot

Men's Hush Puppies Detroit Chukka Boot - Black - Casual boots Own your weekend look with the Detroit chukka boot by Hush Puppies. It features water-resistant WorryFree® leather upper, recycled sock lining and supportive Bounce® and Memory foam footbed... more

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

Jack Chukka Boot

Men's Eastland Jack Chukka Boot - Brown - Casual boots Burnished leather and a streamlined silhouette add modern sophistication to a versatile chukka boot designed with optimal cushioning and a flexible sole. more

Theo Chukka Boot

Men's Børn Theo Chukka Boot - Blue - Casual boots Handcrafted of full-grain leather using signature Opanka construction for a flexible fit, this sporty chukka boot is sure to become your everyday go-to. more

Chukka Boots

Men's COACH Chukka Boots - Black - Casual boots Ankle-high paneled coated canvas and buffed leather boots in black. more

Chukka Boot

Men's Taft Chukka Boot - Black - Casual boots Add to your professional wardrobe with the TAFT Chukka boot. Crafted from premium leather, this pair sports a classic look that pairs well with all manner of professional or formal ensemble. Leather upper.... more

Reebok Postal Express Chukka Boots - Men's Black 5.5 Medium 690774227460

Reebok Postal Express Chukka Boots - Men's Black 5.5 Medium 690774227460. Specifications for Reebok Postal Express Chukka Boots - Men's: Manufacturer: Reebok Gender: Male Footwear Type: Boots Toe Type: Soft Color: Black Footwear Upper Fabric/Material:... more

Camron Chukka Boot

Men's Dune Camron Chukka Boot - Brown - Casual boots Smarten up your daily look with a classic chukka boot crafted from luxe leather and grounded by a contemporary wedge sole with cleated traction. more

Gomma Chukka Boot

Men's Tod's Gomma Chukka Boot - Brown - Casual boots The brand's monogram is artfully, subtly etched into the suede of this luxurious chukka boot classic in every way but for the pebbled-tread sole. Lace-up style Leather upper and lining/rubber sole... more

Break Chukka Boots

Men's Rockport Break Chukka Boots - Brown - Casual boots The Rockport Classic Break Chukka has versatile style to get you through the day and into the evening. Premium leather or suede uppers. Lace-up closure. Soft knit fabric linings. EVA footbed and... more

Readhead Chukka Boot

Men's Barbour Readhead Chukka Boot - Purple - Casual boots Burnished leather elevates a versatile chukka boot in a clean, classic silhouette. more

'harrison' Chukka Boot

Men's Børn 'harrison' Chukka Boot - Brown - Casual boots Opanka construction lends signature comfort to a classically styled chukka boot crafted from vintaged leather. Lace-up style. Steel shank support. Leather upper and lining/rubber sole. Available... more

Bridgeport 2 Chukka Boot

Men's Hush Puppies Bridgeport 2 Chukka Boot - Brown - Casual boots Authentic style and hug-like comfort technology are why you should opt the Hush Puppies Bridgeport 2 chukka boot. Apart from these, this ankle boot comes with feel-good suede, extended... more

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

Earl 04 Chukka Boot

Men's Josef Seibel Earl 04 Chukka Boot - Brown - Casual boots High-quality full-grain leather defines a stylish chukka boot built with a flexible, durable sole and cushioned arch support. more

The Livingston Chukka Boot

Men's Taft The Livingston Chukka Boot - Brown - Casual boots Soft felted fabric is surrounded by smooth leather on this versatile chukka boot that brings sophisticated style to any ensemble. 4" shaft Lace-up style Cushioned footbed Leather upper and... more

Banks Chukka Boot

Men's Thomas & Vine Banks Chukka Boot - Black - Casual boots Get the trend-right look with the Banks chukka boot by Thomas & Vine. This ankle boot made using genuine leather keeps you cozy with a Tru Comfort foam insole. An Extralight EVA sole keeps... more

George Chukka Boot

Men's Anthony Veer George Chukka Boot - Blue - Casual boots Accent a formal or professional look with the laidback George chukka boot from Anthony Veer. This leather pair sports an OrthoLite footbed for added comfort. Suede upper. Lace-up closure.... more

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

Upton Chukka Boot

Men's Johnston & Murphy Upton Chukka Boot - Brown - Casual boots Minimal detailing brings maximum versatility to a wardrobe-staple chukka boot shaped from rich full-grain leather with luxe memory foam cushioning underfoot. more

Theo Chukka Boot

Men's Thomas & Vine Theo Chukka Boot - Brown - Casual boots The Theo chukka boot from Thomas & Vine is a happy medium between casual and formal. Boasting a low-cut profile, this boot showcases 12mm Tru Comfort Foam insole that delivers cushioned... more

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