Best Seller
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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Theo Chukka Boot

Theo Chukka Boot

Men's Born Theo Chukka Boot - Brown - Casual boots A sophisticated mix of timeless style and modern comfort, the Theo chukka boot from Born smoothly transitions from workdays to weekends. This lace-up boot features a hand-finished leather upper that... more

$129.99

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Best Seller
Colton Chukka Boot

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

$165.00

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Morello Chukka Boot

Morello Chukka Boot

Men's Carlos By Carlos Santana Morello Chukka Boot - Blue - Casual boots Sharpen up a formal look with the suave Morello chukka boot from Carlos by Carlos Santana. Croc-print detailing along the leather upper brings in ferocious style, while the... more

$149.99

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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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Husky Chukka Boot

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

$179.00

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Camron Chukka Boot

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

$150.00

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Bowery Chukka Boots

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

$328.00

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Chukka Boot

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

$294.99

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Seneca Camp Moc Chukka Boot

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

$125.00 $90.00

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Austin Chukka Boot

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

$265.00 $174.90

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Leandro Chukka Boot

Leandro Chukka Boot

Men's Vince Camuto Leandro Chukka Boot - Brown - Casual boots Whether it's a casual gathering or a formal meeting, the Leandro Chukka boot from Vince Camuto is a relevant pick. Classic lace-up silhouette with luxe leather upper and light burnished toe... more

$109.99 $69.98

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Renton Chukka Boot

Renton Chukka Boot

Men's Crown Vintage Renton Chukka Boot - Brown - Casual boots The Renton chukka boot from Crown Vintage is a put-together yet practical footwear option. Crafted from leather for a look that improves with every wear. Leather upper. Lace-up closure.... more

$59.99

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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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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 $136.00

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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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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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Chukka Boot

Chukka Boot

Men's Taft Chukka Boot - Brown - Casual boots Minimal detailing brings maximum versatility to a wardrobe-staple chukka boot shaped from rich pebbled leather. Lace-up style Leather upper and lining/rubber sole Made in Spain. more

$295.00

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Wilson Chukka Boot

Wilson Chukka Boot

Men's Anthony Veer Wilson Chukka Boot - Brown - Casual boots Your smart looks get a touch of elegance with the Wilson Chukka boot by Anthony Veer. This leather boot is improved with the Goodyear welt construction, leather lining and cushioned Ortholite... more

$139.99

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Attleboro Chukka Boot

Attleboro Chukka Boot

Men's Timberland Attleboro Chukka Boot - Black - Casual boots Step out in handsome style with the Attleboro Chukka boot from Timberland. Crafted from premium Timberland leather upper for long-term wear, this boot comes with steel shank for enhanced... more

$129.99

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Papakū 'ili Waterproof Chukka Boot

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

$160.00

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Len Chukka Boot

Len Chukka Boot

Men's Sandro Moscoloni Len Chukka Boot - Blue - Casual boots Showcasing broguing detailing, this Sandro Moscoloni Len chukka boot adds subtle elegance to any of your formal outfit. Made of leather, this 3-eyelet boot has almond toe, leather lining,... more

$149.99

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The Livingston Chukka Boot

The Livingston Chukka Boot

Men's Taft The Livingston Chukka Boot - Black - 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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Landon Chukka Boot

Landon Chukka Boot

Men's Sandro Moscoloni Landon Chukka Boot - Black - Casual boots Bring a sleek look to your formal wear with the Landon boot from Sandro Moscoloni. This lace-up pair features a smooth leather upper and rubber sole for durable wear! Leather upper.... more

$179.99

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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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Jack Chukka Boot

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

$125.00

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Alder Chukka Boot

Alder Chukka Boot

Men's Blake McKay Alder Chukka Boot - Black - Casual boots Your casual look will get a whole lot better with the Blake McKay Alder Chukka boot. With a plush OrthoLite footbed and durable rubber sole, you will love to wear this classic leather lace-up.... more

$164.99

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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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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

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Clinton Chukka Boot

Clinton Chukka Boot

Men's ALDO Clinton Chukka Boot - Brown - Casual boots Elevate your style statement with the Aldo Clinton chukka boot. The leather-blend lace-up comes with a memory foam footbed for daylong comfort. A contrasting sole brings a sporty element. Leather &... more

$129.99

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Clarks(r) Torhill Hi Chukka Boot

Clarks(r) Torhill Hi Chukka Boot

Men's Clarks(r) Torhill Hi Chukka Boot - White - Casual boots Smooth leather and soft sheepskin lining enrich a handsome boot in a classic silhouette with a chunky rubber sole. more

$130.00

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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

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Leandro Chukka Boot

Leandro Chukka Boot

Men's Vince Camuto Leandro Chukka Boot - Brown - Casual boots Whether it's a casual gathering or a formal meeting, the Leandro Chukka boot from Vince Camuto is a relevant pick. Classic lace-up silhouette with luxe leather upper and light burnished toe... more

$109.99 $59.98

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Wilson Chukka Boot

Wilson Chukka Boot

Men's Anthony Veer Wilson Chukka Boot - Black - Casual boots Your smart looks get a touch of elegance with the Wilson Chukka boot by Anthony Veer. This leather boot is improved with the Goodyear welt construction, leather lining and cushioned Ortholite... more

$199.99

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Corazon Chukka Boot

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

$153.99

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Renton Chukka Boot

Renton Chukka Boot

Men's Crown Vintage Renton Chukka Boot - Brown - Casual boots The Renton chukka boot from Crown Vintage is a put-together yet practical footwear option. Crafted from leather for a look that improves with every wear. Leather upper. Lace-up closure.... more

$59.99

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Alto Suede Chukka Boot

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

$349.00

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Papakū 'ili Waterproof Chukka Boot

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

$160.00

FREE shipping

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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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More information about Men's Shoes

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