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Earl 04 Chukka Boot

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

$160.00

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The Livingston Chukka Boot

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

$295.00

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Best Seller
Banks Chukka Boot

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

$94.99

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George Chukka Boot

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

$165.99

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Reebok Postal Express Chukka Boots - Men's Black 5.5 Wide 690774227507

Reebok Postal Express Chukka Boots - Men's Black 5.5 Wide 690774227507

Reebok Postal Express Chukka Boots - Men's Black 5.5 Wide 690774227507. 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

$229.00

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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

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Keegan Chukka Boot

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

$84.99

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The Livingston Chukka Boot

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

$295.00

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Clarks(r) Wallabee Chukka Boot

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

$180.00

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Austin Chukka Boot

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

$265.00

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Rock Chukka Boot

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

$820.00 $451.00

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Maple Grove Chukka Boot

Maple Grove Chukka Boot

Men's Timberland Maple Grove Chukka Boot - Brown - 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

$125.00

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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

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Earl 04 Chukka Boot

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

$160.00

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Reebok Postal Express Chukka Boots - Men's Black 4 Medium 690774227439

Reebok Postal Express Chukka Boots - Men's Black 4 Medium 690774227439

Reebok Postal Express Chukka Boots - Men's Black 4 Medium 690774227439. 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

$229.00

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Everyday Chukka Boot

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

$227.99

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Suede Chukka Boot

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

$945.00

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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

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Readhead Chukka Boot

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

$220.00

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Seneca Chukka Boot

Seneca Chukka Boot

Men's Eastland Seneca Chukka Boot - Brown - Casual boots A traditional look of a camp moccasin combined with the styling of the chukka boot makes the Seneca from Eastland one great choice! Lace up this leather chukka boot with jeans or khakis for a... more

$99.99

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Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 14 W)

Wide Width Men's Deer Stags® Warren™ Chukka Boot by Deer Stags in Black (Size 14 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

$124.99 $74.99

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Davis Square Chukka Boot

Davis Square Chukka Boot

Men's Timberland Davis Square Chukka Boot - Brown - Casual boots Elevate your casual wardrobe with the Davis Square chukka boot from Timberland. The plush trim on the collar lend a cozy touch, while the Defender Repellent Systems treatment deters... more

$84.99 $59.98

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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

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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

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Chandler Chukka Boot

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

$475.00

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Alder Chukka Boot

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

$165.00 $119.90

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George Chukka Boot

George Chukka Boot

Men's Anthony Veer George Chukka Boot - Brown - 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

$165.99

FREE shipping

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Everyday Chukka Boot

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

$227.99

FREE shipping

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Corazon Chukka Boot

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

$153.99

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Jack Chukka Boot

Jack Chukka Boot

Men's Eastland Jack Chukka Boot - Brown - Casual boots The Jack chukka boot from Eastland will be perfect for your day-to-day lifestyle. This lace-up features a full grain leather upper and a Memory Foam insole that will leave you with daylong comfort!... more

$119.99

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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

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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

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

$155.00

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Otto Plain Toe Chukka Boot

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

$89.99

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Austin Chukka Boot

Austin Chukka Boot

Men's Gordon Rush Austin Chukka Boot - Black - 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

$265.00

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Larrado Weatherproof Chukka Boot

Larrado Weatherproof Chukka Boot

Men's Ron White Larrado Weatherproof Chukka Boot - Black - 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

$545.00

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Clarks(r) Wallabee Chukka Boot

Clarks(r) Wallabee Chukka Boot

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

$170.00

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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

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Manoa Chukka Boot

Manoa Chukka Boot

Men's Steve Madden Manoa Chukka Boot - Brown - Casual boots With a classic design and a leather construction, the Manoa chukka boot from Steve Madden is an easy add to your everyday looks. The versatile option features a simple silhouette, complete... more

$139.99

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Men's Seneca Camp Moc Chukka Boots by Eastland® in Tan (Size 9 1/2 M)

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

$110.00

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X Aries Ua Og Chukka Boots

X Aries Ua Og Chukka Boots

Men's Vans X Aries Ua Og Chukka Boots - Pink - Casual boots Dimensions: Height: 9.5cm, Sole: 3cm 100% Leather, 100% Cotton, 100% Rubber. Made in Vietnam. more

$128.96

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