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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 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 Kendrick Chelsea Boots
Black Harness Full-Grain
Tan Harness Full-Grain
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Men's Kendrick Chelsea Boots
$140.00
Men's Killington Chukka Sneaker Boots
Brown Full-Grain/Mesh
Brown Full-Grain/Mesh
Black Full-Grain/Mesh
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Men's Killington Chukka Sneaker Boots
$125.00
Men’s FlyRoam™ Go Leather Chukka Sneakers
Burgundy Nubuck
Black Nubuck
Light Tan Nubuck
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Men’s FlyRoam™ Go Leather Chukka Sneakers
$130.00
Men's Brook Park Leather Chukka Shoes
Red Brown Smooth
Black Smooth
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Men's Brook Park Leather Chukka Shoes
$130.00
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 Radford Waterproof Chukka Boots
Dark Brown Nubuck
Light Brown Nubuck
Navy Nubuck
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Men's Radford Waterproof Chukka Boots
$160.00
Men's Timberland® Waterproof Chukka Boots
GORE-TEX®
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Men's Timberland® Waterproof Chukka Boots
$140.00
Men's Altimeter Mixed-Media Sneaker Boots
Black Full-Grain/Mesh
Light Taupe Full-Grain/Mesh
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Men's Altimeter Mixed-Media Sneaker Boots
$130.00 $89.99
Men's Groveton Chukka Shoes
Black Nubuck/Canvas
Grey Nubuck/Canvas
Wheat Nubuck
Grey Nubuck/Cordura® Canvas
Green Nubuck/Cordura® Canvas
Light Brown Nubuck/Cordura® Canvas
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Men's Groveton Chukka Shoes
$80.00
Men's Adventure Cupsole Chukka Shoes
Light Brown Nubuck
Burnished Wheat Nubuck
Olive Full-Grain
Medium Brown Full-Grain
Green Nubuck
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Men's Adventure Cupsole Chukka Shoes
$110.00
Men's Davis Square Mixed-Media Chukka Shoes
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
$90.00
Men’s Killington Leather Chukka Sneaker Boots
Wheat Nubuck
Navy Nubuck
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Men’s Killington Leather Chukka Sneaker Boots
$125.00
Men's Kingspoint Chukka Boots
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Men's Kingspoint Chukka Boots
$190.00
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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Men's Amherst High-Top Chukka Shoes
$125.00
Men's Groveton Chukka Shoes
Grey Nubuck/Cordura® Canvas
Grey Nubuck/Canvas
Black Nubuck/Canvas
Wheat Nubuck
Green Nubuck/Cordura® Canvas
Light Brown Nubuck/Cordura® Canvas
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Men's Groveton Chukka Shoes
$80.00
Men's Amherst High-Top Chukka Shoes
Light Brown Nubuck
Black Full-Grain
Black Nubuck
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Men's Amherst High-Top Chukka Shoes
$125.00
Men's Timberland Boot Company® Bardstown Cupsole Chukka Boots
Dark Brown Full-Grain
Dark Grey Full-Grain
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Men's Timberland Boot Company® Bardstown Cupsole Chukka Boots
$210.00
Men's Timberland Boot Company® Bardstown Cupsole Chukka Boots
Dark Grey Full-Grain
Dark Brown Full-Grain
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Men's Timberland Boot Company® Bardstown Cupsole Chukka Boots
$210.00
Men's Killington Chukka Sneaker Boots
Black Full-Grain/Mesh
Brown Full-Grain/Mesh
Brown Full-Grain/Mesh
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Men's Killington Chukka Sneaker Boots
$125.00
Men's Timberland® Waterproof Chukka Boots
Black Smooth
Wheat Nubuck
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Men's Timberland® Waterproof Chukka Boots
$135.00
Men's Timberland Boot Company® Wodehouse Chukka Shoes
Dark Brown Vintage
Burnished Black
Burnished Dark Brown
Light Brown Full-Grain
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Men's Timberland Boot Company® Wodehouse Chukka Shoes
$300.00
Men's Franklin Park Brogue Chukka Shoes
Light Taupe Nubuck
Black Full-Grain
Brown Nubuck
Brown Full-Grain
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Men's Franklin Park Brogue Chukka Shoes
$160.00
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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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