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Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 12 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

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

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

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

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

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

Seneca Camp Moc Chukka Boot

Men's Eastland Seneca Camp Moc Chukka Boot - Brown - Casual boots Crafted from premium leather, this classic chukka boot is hand-sewn with a memory foam footbed and slip-resistant outsole for both city and outdoor wear. more

Clarks(r) Wallabee Chukka Boot

Men's Clarks(r) Wallabee Chukka Boot - Brown - Boots A durable crepe rubber sole grounds a classic chukka boot done in a retro checked suede with perforations on the footbed for ventilation. Leather upper and lining/synthetic sole Made in Portugal. more

Austin Chukka Boot

Men's Gordon Rush Austin Chukka Boot - Brown - Casual boots Elevate your work-to-weekend look in this refined Italian-leather chukka boot featuring Blake stitch construction, breathable lining and an Ortho Lite® insole. more

Theo Chukka Boot

Men's Børn Theo Chukka Boot - Brown - 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

Bushacre Chukka Boot

Men's Clarks Bushacre Chukka Boot - Brown - Casual boots Go for classic appeal in the Bushacre chukka boot from Clarks. The smooth leather upper and Ultimate Comfort footbed work together for high-quality style you can pair with any outfit. Leather or... more

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

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

Husky Chukka Boot

Men's Warfield & Grand Husky Chukka Boot - Brown - Casual boots Classic chukka styling defines this handsome leather boot furnished with an arch-supporting footbed and set on a slim rubber sole. more

Alden For Unlined Chukka Boots

Men's J.Crew Alden For Unlined Chukka Boots - Brown - Casual boots Founded in Massachusetts by Charles H. Alden in 1884, the Alden Shoe Company is now in its fourth generation, making it the oldest shoemaker in New England. This handsome chukka is... 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

Papakū 'ili Waterproof Chukka Boot

Men's Olukai Papakū 'ili Waterproof Chukka Boot - Brown - Casual boots This waterproof-leather chukka boot will be a cold-weather go-to thanks to its plush quilted lining and a Wet Grip rubber sole providing superior traction. more

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

Readhead Chukka Boot

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

Everyday Chukka Boot

Men's Nisolo Everyday Chukka Boot - Brown - 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

Toby Chukka Boot

Men's Blake McKay Toby Chukka Boot - Brown - Casual boots Natural rubber crepe soles cushion every step you take in these versatile chukka boots that develop more interesting character with wear. Leather upper and lining/rubber sole Made in Brazil. 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

Colton Chukka Boot

Men's Blake McKay Colton Chukka Boot - Brown - Casual boots Contrast stitching highlights the classic silhouette of a smooth leather chukka boot grounded by a cushioned, arch-supporting OrthoLite® footbed. more

Suede Chukka Boot

Men's Brunello Cucinelli Suede Chukka Boot - Brown - Casual boots Clean lines and minimal detailing keep things casual and relaxed in a chukka boot that sets brushed Italian suede on a bright rubber sole. Lace-up style Leather upper and lining/rubber... more

Chandler Chukka Boot

Men's Allen Edmonds Chandler Chukka Boot - Brown - Casual boots Premium, finely napped suede elevates a classic chukka boot handcrafted with a comfortable cork insole, durable bench welt and rubber grip sole. 360o welt construction for durability and... more

Alder Chukka Boot

Men's Blake McKay Alder Chukka Boot - Brown - 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

Papakū 'ili Waterproof Chukka Boot

Men's Olukai Papakū 'ili Waterproof Chukka Boot - Brown - Casual boots This waterproof-leather chukka boot will be a cold-weather go-to thanks to its plush quilted lining and a Wet Grip rubber sole providing superior traction. more

Corazon Chukka Boot

Men's Carlos By Carlos Santana Corazon Chukka Boot - Brown - Casual boots Add tailored appeal to any outfit with the Corazon chukka boot from Carlos by Carlos Santana. A soft suede upper, breathable leather lining, and sleek 3-eye lace-up keep this... 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

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

Clarks(r) Wallabee Chukka Boot

Men's Clarks(r) Wallabee Chukka Boot - Brown - Casual boots A pebbly crepe-rubber sole grounds an iconic leather chukka boot complete with a smartly stitched toe and tonal fobs. more

Toby Chukka Boot

Men's Blake McKay Toby Chukka Boot - White - Casual boots Natural rubber crepe soles cushion every step you take in these versatile chukka boots that develop more interesting character with wear. Leather upper and lining/rubber sole Made in Brazil. more

Richard Chukka Boot

Men's To Boot New York Richard Chukka Boot - Brown - Casual boots Soft suede adds a laid-back vintage-inspired touch to this dapper Italian-made chukka boot built on a sturdy leather sole featuring grippy rubber tread. Leather upper and lining/rubber... more

Cairngorm Chukka Boot

Men's Barbour Cairngorm Chukka Boot - Brown - Casual boots Lightly weathered leather elevates a waterproof chukka boot in a classic silhouette. more

Taddeo Suede Chukka Boots

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