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MEN’S CHUKKAS

Men’s chukka boots have been in style for more than a century, starting as desert boots and evolving throughout the 1900s into much more than just standard men’s leather boots. Their distinctive mid height and versatility in material and style makes our chukkas some of our most popular footwear styles.

Men's Kendrick Chelsea Boots
Black Harness Full-Grain
Tan Harness Full-Grain
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Men's Kendrick Chelsea Boots
$140.00
Men’s Bradstreet Leather Chukka Sneaker Boots
Wheat Nubuck
Black Nubuck
Brown Full-Grain
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Men’s Bradstreet Leather Chukka Sneaker Boots
$120.00
Men’s FlyRoam™ Go Chukka Sneakers
Black Full-Grain/Mesh
Dark Green Full-Green/Mesh
Grey Full-Grain/Mesh
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Men’s FlyRoam™ Go Chukka Sneakers
$120.00
Men's Killington Chukka Sneaker Boots
Brown Full-Grain/Mesh
Black Full-Grain/Mesh
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Men's Killington Chukka Sneaker Boots
$125.00
Men's Timberland® Waterproof Chukka Boots
GORE-TEX®
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Men's Timberland® Waterproof Chukka Boots
$140.00
Men's Kendrick Chukka Boots
Tan Harness Full-Grain
Black Harness Full-Grain
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Men's Kendrick Chukka Boots
$140.00
Men's Altimeter Mixed-Media Sneaker Boots
Black Full-Grain/Mesh
Light Taupe Full-Grain/Mesh
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EXTRA 30% OFF- IN CART
Men's Altimeter Mixed-Media Sneaker Boots
$130.00 $89.99
Men's Kingspoint Chukka Boots
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EXTRA 30% OFF- IN CART
Men's Kingspoint Chukka Boots
$190.00 $169.99
Men's Amherst High-Top Chukka Shoes
Light Brown Nubuck
Black Full-Grain
Black Nubuck
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EXTRA 30% OFF- IN CART
Men's Amherst High-Top Chukka Shoes
$125.00 $99.99
Men's Timberland Boot Company® Bardstown Cupsole Chukka Boots
Dark Brown Full-Grain
Dark Grey Full-Grain
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EXTRA 30% OFF- IN CART
Men's Timberland Boot Company® Bardstown Cupsole Chukka Boots
$210.00 $169.99
Men's Franklin Park Brogue Chukka Shoes
Light Taupe Nubuck
Black Full-Grain
Brown Nubuck
Brown Full-Grain
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EXTRA 30% OFF- IN CART
Men's Franklin Park Brogue Chukka Shoes
$160.00 $119.99
Men’s FlyRoam™ Leather Sneaker Boots
Black Full-Grain
Grey Nubuck
Black Nubuck
Navy Suede
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EXTRA 30% OFF- IN CART
Men’s FlyRoam™ Leather Sneaker Boots
$140.00 $99.99
Men's Killington Chukka Sneaker Boots
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EXTRA 30% OFF- IN CART
Men's Killington Chukka Sneaker Boots
$125.00 $114.99
Men’s Amherst High-Top Chukka Sneakers
Black Full-Grain
Black Nubuck
Light Brown Nubuck
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EXTRA 30% OFF- IN CART
Men’s Amherst High-Top Chukka Sneakers
$125.00 $99.99
Men's Timberland Boot Company® Wodehouse Chukka Shoes
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EXTRA 30% OFF- IN CART
Men's Timberland Boot Company® Wodehouse Chukka Shoes
$300.00 $269.99
Men's Davis Square Mixed-Media Chukka Shoes
Navy Nubuck/Cordura® Canvas
Black Nubuck/Cordura® Canvas
Black Nubuck/Cordura® Canvas
Red Nubuck/Cordura® Canvas
Wheat Nubuck/Cordura® Canvas
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EXTRA 30% OFF- IN CART
Men's Davis Square Mixed-Media Chukka Shoes
$90.00 $79.99
Men's Davis Square Mixed-Media Chukka Shoes
Black Nubuck/Cordura® Canvas
Navy Nubuck/Cordura® Canvas
Black Nubuck/Cordura® Canvas
Red Nubuck/Cordura® Canvas
Wheat Nubuck/Cordura® Canvas
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Men's Davis Square Mixed-Media Chukka Shoes
$80.00
Men’s FlyRoam™ Go Leather Chukka Sneakers
Burgundy Nubuck
Black Nubuck
Light Tan Nubuck
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EXTRA 30% OFF- IN CART
Men’s FlyRoam™ Go Leather Chukka Sneakers
$130.00 $109.99
Men's Groveton Chukka Shoes
Black Nubuck/Canvas
Grey Nubuck/Canvas
Wheat Nubuck
Grey Nubuck/Cordura® Canvas
Green Nubuck/Cordura® Canvas
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Men's Groveton Chukka Shoes
$80.00
Men's Adventure Cupsole Chukka Shoes
Light Brown Nubuck
Green Nubuck
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EXTRA 30% OFF- IN CART
Men's Adventure Cupsole Chukka Shoes
$110.00 $99.99
Men’s Killington Leather Chukka Sneaker Boots
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Men’s Killington Leather Chukka Sneaker Boots
$125.00
Men’s FlyRoam™ Go Chukka Sneakers
Dark Green Full-Green/Mesh
Black Full-Grain/Mesh
Grey Full-Grain/Mesh
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Men’s FlyRoam™ Go Chukka Sneakers
$120.00
Men's Amherst High-Top Chukka Shoes
Black Nubuck
Black Full-Grain
Light Brown Nubuck
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EXTRA 30% OFF- IN CART
Men's Amherst High-Top Chukka Shoes
$125.00 $99.99
Men's Timberland Boot Company® Bardstown Cupsole Chukka Boots
Dark Grey Full-Grain
Dark Brown Full-Grain
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EXTRA 30% OFF- IN CART
Men's Timberland Boot Company® Bardstown Cupsole Chukka Boots
$210.00 $169.99
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MEN'S CHUKKA BOOTS

Timberland® men's chukkas have become some of our most popular footwear. Try a pair of our men's chukka boots for the ultimate smooth ride and a modern look that blends athletic styling with heritage details. Versatility comes standard: Our Timberland® chukka boots work for everything from casual Fridays to date nights.

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