Best Seller
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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Upton Chukka

Upton Chukka

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

$169.00

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Best Seller
Len Chukka Boot

Len Chukka Boot

Men's Sandro Moscoloni Len Chukka Boot - Brown - 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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Larrado Weatherproof Chukka Boot

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

$545.00

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Vandick Chukka Boot

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

$198.99

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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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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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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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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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Theo Chukka Boot

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

$130.00

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Gomma Chukka Boot

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

$745.00

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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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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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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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Chukka 2.1 Boots

Chukka 2.1 Boots

Men's Boris Bidjan Saberi Chukka 2.1 Boots - Black - Casual boots Handcrafted ankle-high vegetable-tanned polished horse leather boots in black. Distressing and crinkling throughout. more

$1,550.00 $961.00

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Keith Chukka Boot

Keith Chukka Boot

Men's Drew Keith Chukka Boot - Brown - Casual boots Stay stylish without sacrificing comfort with the Keith chukka boot from Drew. This ankle boot features a Gel System footbed and sole to absorb impact! Leather upper. Lace-up closure. Padded collar.... more

$193.99

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Theo Chukka Boot

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

$130.00

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Shawn Chukka Boot

Shawn Chukka Boot

Men's Sandro Moscoloni Shawn Chukka Boot - Brown - Casual boots The Shawn 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 layer.... more

$198.99

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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

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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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Mason Chukka Boot

Mason Chukka Boot

Men's Barbour Mason Chukka Boot - Brown - Casual boots Embossed logos brand a smooth-suede chukka boasting arch support and a sneaker-inspired cupsole. Removable insole with arch support Leather upper/textile lining/synthetic sole Made in Portugal. more

$190.00

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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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Morello Chukka Boot

Morello Chukka Boot

Men's Carlos By Carlos Santana Morello Chukka Boot - Brown - 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

$112.99

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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 - 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

FREE shipping

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Jack Chukka Boot

Jack Chukka Boot

Men's Eastland Jack Chukka Boot - Brown - Casual boots Add a rugged distinction to your street-ready attire with this Eastland Jack chukka boot. Rendered in durable full grain leather, this lace-up boot has Active Memory Foam cushioned insole for... more

$119.99

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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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Bilton Chukka Boot

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

$289.00

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Kent Chukka Boot

Kent Chukka Boot

Men's Barbour Kent Chukka Boot - Brown - Casual boots A suede desert boot stays grounded by a branded traction sole and features arch support for daylong comfort. Removable insole Leather upper/textile lining/synthetic sole Made in Portugal. more

$180.00

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Livingston Chukka Boot

Livingston Chukka Boot

Men's Taft Livingston Chukka Boot - Brown - Casual boots Dare to experiment with the bold Livingston Chukka boot from Taft. Camo-printed inlays give an offbeat look to the clean leather upper of this chukka boot. Brogue accentuation elevates the style,... more

$294.99

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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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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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Shawn Chukka Boot

Shawn Chukka Boot

Men's Sandro Moscoloni Shawn Chukka Boot - Blue - Casual boots The Shawn 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 layer.... more

$198.99

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Reverb Chukka Boot

Reverb Chukka Boot

Men's Barbour Reverb Chukka Boot - Brown - Casual boots The brand's iconic tartan makes a discreet appearance at the pull-tab of a streamlined chukka boot crafted from buttery-smooth, matte-finish nubuck leather. Lace-up style Removable, cushioned... more

$215.00

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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

$123.11

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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

FREE shipping

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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

$116.99

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Ozark Chukka Boot

Ozark Chukka Boot

Men's Nunn Bush Ozark Chukka Boot - Brown - Casual boots Perfect your look with the Ozark chukka boot from Nunn Bush. Enhanced with brogue-inspired details, this lace-up boot comes with a memory foam insole that delivers maximum comfort. Leather upper.... more

$104.99 $79.98

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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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More information about Men's Shoes

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