Category: Chukka Boots
-48% Clarks Men’s Gleeson Hi GTX Chukka Boot,Black,13 M US

Clarks Men’s Gleeson Hi GTX Chukka Boot,Black,13 M US

Designed for looks and built for comfort, this men's lace-up boot from the Tor collection has everything you need for your busiest--and most stylish--days. It's made of rich ...

$88.12 $170.00

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-1% Clarks Men’s Desert Chukka Boot,Stone Camo Suede,7.5 M US

Clarks Men’s Desert Chukka Boot,Stone Camo Suede,7.5 M US

An international cult classic, the iconic men's Desert Boot by Clarks Originals was inspired by crepe-soled boots worn by British officers in World War II. Crafted from natural ...

$119.99 $120.00

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-47% Clarks Men’s Desert Chukka Boot,Sage,10 M US

Clarks Men’s Desert Chukka Boot,Sage,10 M US

Clarks Originals Desert Boot

$69.99 $130.00

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-1% Dunham by New Balance Men’s Addison Chukka Boot, Dark Brown, 11.5 6E US

Dunham by New Balance Men’s Addison Chukka Boot, Dark Brown, 11.5 6E US

Stay comfortable with the Dunham Windsor Mid Cut Boot. The waterproof leather upper of this men's casual boot has a Tectonic TongueTM for an increased range of motion. The Rollbar ...

$139.95 $140.00

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Volcom Men’s Del Mesa Chukka Boot, Vintage Brown, 10.5 M US

Volcom Men’s Del Mesa Chukka Boot, Vintage Brown, 10.5 M US

Volcom Del Mesa boots. The deconstructed Chukka styling of the Del Mesa Shoe screams casual comfort. Asymmetrical details paired with a direct attached molded circle stone and ...

$85.00 $85.00

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-23% Calvin Klein Men’s Ulysses Suede Boot,Dark Brown,9.5 M US

Calvin Klein Men’s Ulysses Suede Boot,Dark Brown,9.5 M US

Be classically stylish in the Ulysses Chukka Boot by Calvin Klein.Suede upper in a casual chukka boot styleRound toeLace up frontSmooth lining with a cushioning footbedDecorative ...

$77.99 $100.00

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-23% Steve Madden Men’s Garisonn Chukka Boot,Brown,7.5 M US

Steve Madden Men’s Garisonn Chukka Boot,Brown,7.5 M US

Steve Madden, the company, was founded by Steve Madden, the man, in 1990 in Brooklyn, where he started out making trend-advancing shoes one pair at a time. It was not long after ...

$89.99 $115.00

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Clarks Men’s Cobalt Suede Stinson Hi 11 D(M) US

Clarks Men’s Cobalt Suede Stinson Hi 11 D(M) US

Get relaxed style with the Clarks Stinson Hi ankle boot. This men's Wallabee-inspired ankle boot features a suede or leather upper with tonal laces for a snug fit; moccasin-style ...

$109.94 $109.94

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Clarks Men’s Cobalt Suede Stinson Hi 10.5 D(M) US

Clarks Men’s Cobalt Suede Stinson Hi 10.5 D(M) US

Get relaxed style with the Clarks Stinson Hi ankle boot. This men's Wallabee-inspired ankle boot features a suede or leather upper with tonal laces for a snug fit; moccasin-style ...

$109.94 $109.94

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GBX 09130 Mens 3 Eyelet Chukka Boot,Black,15M

GBX 09130 Mens 3 Eyelet Chukka Boot,Black,15M

One of the most iconic silhouettes in mens footwear, the Channing chukka boot delivers casual sophistication with just a dash of attitude.

$80.00 $80.00

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-3% Steve Madden Men’s Kiero Chukka Boot,Black,9 M US

Steve Madden Men’s Kiero Chukka Boot,Black,9 M US

This modern high fashion dress boot by Steve Madden will be a show stopper this season.

$121.20 $125.00

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-1% Florsheim Men’s Casey Plain Toe Chukka Boot, Cognac, 9 D US

Florsheim Men’s Casey Plain Toe Chukka Boot, Cognac, 9 D US

Sometimes less is more. ThereÆs a simple shoe solution to all of your wardrobe problems. With its smooth leather and classic, clean design, the Casey Chukka Boot is all you need.

$119.95 $120.00

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-18% Clarks Men’s Newbern Up Chukka Boot, Brown Leather, 11 M US

Clarks Men’s Newbern Up Chukka Boot, Brown Leather, 11 M US

There's nothing traditional about this men's low-cut boot. Crafted of leather, suede, and fabric, it has a design that's a little rugged and a little urban, with a heavy dose of ...

$82.05 $100.00

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-45% Woolrich Men’s Lane Chukka Boot, Yellow Stone, 9 M US

Woolrich Men’s Lane Chukka Boot, Yellow Stone, 9 M US

Deconstructed to utter simplicity for a natural feel and a clean, uncluttered look, the Woolrich Lane chukka is the epitome of casual style. Featuring an upper of premium Charles ...

$88.73 $160.00

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-1% Johnston & Murphy Men’s McGuffey Chukka Boot, Taupe Suede, 10.5 M US

Johnston & Murphy Men’s McGuffey Chukka Boot, Taupe Suede, 10.5 M US

strobel cement construction, water resistant uppers, padded leather and fabric footbed, rubber outsole

$124.95 $125.00

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-12% Stacy Adams Men’s Astro Chukka Boot,Black Smooth,8 M US

Stacy Adams Men’s Astro Chukka Boot,Black Smooth,8 M US

A timeless design for a well-appointed casual wardrobe, the Stacy Adams Astro chukka brings a refined panache along with lightweight comfort. Featuring an upper of rich suede, ...

$79.99 $90.00

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-34% Rockport Men’s Charson Lace-Up Boot,Dark Brown Crazy Horse,10.5 W US

Rockport Men’s Charson Lace-Up Boot,Dark Brown Crazy Horse,10.5 W US

Men's Rockport, Charson Chukka Boots You?ll admire these amazing chukkas! Leather upper Lace up closure for a secure fit Soft fabric lining Removable cushioned footbed for added ...

$92.47 $140.00

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-15% Rockport Men’s City Smart Waterproof Chukka Boot, Black Leather, 10.5 M US

Rockport Men’s City Smart Waterproof Chukka Boot, Black Leather, 10.5 M US

Waterproof and lightweight, the City Smart Waterproof Collection is perfect for when the weather's not on your side but you still need style. Built with Hydro-ShieldTM waterproof ...

$128.00 $150.00

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-26% FRYE Men’s Mason Chukka BootDark Brown-8709512 M US

FRYE Men’s Mason Chukka BootDark Brown-8709512 M US

Moccasin meets desert boot in this rugged offering from FRYE.

$125.00 $168.00

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