Men's Shoes › chukka boots

Otto Plain Toe Chukka Boot

Men's Nunn Bush Otto Plain Toe Chukka Boot - Blue - Casual boots The classic design of the Otto plain toe chukka boot from Nunn Bush brings versatile stylings to your wardrobe. The Defender Repellant upper offers a waterproof finish, while the Memory... more

Chukka Boot

Men's COACH Chukka Boot - Black - Casual boots Inspired by vintage desert boots worn by the military our rugged Chukka features an EVA outsole for comfort and traction. Crafted of soft suede it's finished with smooth leather details and our Signature... more

Tilden Chukka Boot

Men's Stacy Adams Tilden Chukka Boot - Blue - Casual boots You can only up your dapper quo pairing the Tilden chukka boot by Stacy Adams with your outfit. This suede boot is highlighted with contrast welt and stitching details for a stylish look.... 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

Papakū 'ili Waterproof Chukka Boot

Men's Olukai Papakū 'ili Waterproof Chukka Boot - Black - 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

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

Kenetrek Chukka Boots - Men's Brown 9 US Medium KE-0625-3 09.0MED

Kenetrek Chukka Boots - Men's Brown 9 US Medium KE-0625-3 09.0MED. 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

Otto Plain Toe Chukka Boot

Men's Nunn Bush Otto Plain Toe Chukka Boot - Brown - Casual boots The classic design of the Otto plain toe chukka boot from Nunn Bush brings versatile stylings to your wardrobe. The Defender Repellant upper offers a waterproof finish, while the Memory... more

Rawstin Chukka Boot

Men's Tommy Hilfiger Rawstin Chukka Boot - Brown - Casual boots Add a little extra elegance to your smart casual fits with the Tommy Hilfiger Rawstin chukka boot. A cap toe front and contrasting welt stitches add classic fashion touches to this ankle... more

Vaughn Chukka Boot

Men's Vance Co. Vaughn Chukka Boot - Black - Casual boots Opt for the Vance Co. Vaughn chukka boot that goes well with your off-duty style as well as party looks. Rendered in soft vegan synthetic, this boot displays embossed accents for an interesting... more

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

Clarks(r) Wallabee Chukka Boot

Men's Clarks(r) Wallabee Chukka Boot - Blue - Casual boots A natural rubber-crepe sole grounds an iconic chukka boot built with a suede upper, waxy laces and signature tonal logo fobs. 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

Men's Findley Chukka Boots by Propet in Black (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

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

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

Kezar Waterproof Suede Chukka Boots

Men's Sorel Kezar Waterproof Suede Chukka Boots - Brown - Casual boots Sorel "Kezar" waterproof suede boots. Round moccasin toe. Laceup vamp. Logo at tongue. Wool/polyester lining. EVA footbed. Sawtooth rubber sole. Imported. 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

Men's Deer Stags® Bangor Chukka Boots by Deer Stags in Red Wood (Size 13 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

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

Dixon Chukka Boot

Men's Blake McKay Dixon Chukka Boot - Black - Casual boots Premium suede lends old-world charm to this water-repellent Chukka boot with breathable linings and a cushy antimicrobial insole for all-day comfort. more

Norton Chukka Boot

Men's Dockers Norton Chukka Boot - Brown - Casual boots Add a hint of classic flair to your ensemble with the Norton chukka boot from Dockers. This lace-up boot features Supreme Comfort massaging EVA footbed to provide enhanced foot support and 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

Rugged Bucks Chukka Boot

Men's Rockport Rugged Bucks Chukka Boot - Brown - Casual boots Venture out in the wilderness with utmost comfort in the Rockport Rugged Bucks chukka boot. A flexible and outdoor-friendly design, this boot showcases Hydro-Shield construction that... more

Seneca Chukka Boot

Men's Eastland Seneca Chukka Boot - Brown - Casual boots Smarten your outfit with the Seneca chukka boot from Eastland. This lace-up showcases contoured insole with Active Memory Foam for all-day cushioned support and durable outsole that also absorbs... more

Aldwin Chukka Boot

Men's Vintage Foundry Aldwin Chukka Boot - Brown - Casual boots Step into timeless style with the Aldwin Chukka Boot from Vintage Foundry Co. Crafted from luxurious suede and featuring an EVA cushioned footbed along with a durable rubber sole, these... more

Corazon Chukka Boot

Men's Carlos By Carlos Santana Corazon Chukka Boot - Natural - 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

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

Billy Comfort Chukka Boot

Men's BILLY Footwear Billy Comfort Chukka Boot - Black - Casual boots Classic style meets everyday convenience in this versatile chukka boot featuring a wraparound zipper that ensures easy on and off. 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

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

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

Austin Chukka Boot

Men's Gordon Rush Austin Chukka Boot - Purple - 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

Harris Chukka Boot

Men's Allen Edmonds Harris Chukka Boot - Brown - Casual boots Stride in comfort with this stylish boot featuring a shock-absorbing insole and an XL Extralight® XGrip injection sole boasting an abrasion-resistant surface. more

Rock Chukka Boot

Men's Santoni Rock Chukka Boot - Brown - Casual boots Burnished suede lends handsome appeal to a laceless chukka boot set on a robust lug sole. Leather upper and lining/rubber sole Made in Italy. more