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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.

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Men's FlyRoam™ Chill Sneaker Boots
Black Full-Grain
Dark Brown Full-Grain
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Men's FlyRoam™ Chill Sneaker Boots
$150.00
Men's Kendrick Waterproof Chukka Boots
Dark Brown Full-Grain
Black Full-Grain
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Men's Kendrick Waterproof Chukka Boots
$160.00
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 Kendrick Chukka Boots
Tan Harness Full-Grain
Black Harness Full-Grain
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Men's Kendrick Chukka Boots
$140.00
Men's Killington Chukka Sneaker Boots
Brown Full-Grain/Mesh
Black Full-Grain/Mesh
Dark Brown Nubuck
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Men's Killington Chukka Sneaker Boots
$125.00
Men's CityRoam™ Cupsole High-Top Sneakers
Black Nubuck/Canvas
Olive Green Nubuck/Canvas
Beige Nubuck/Canvas
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Men's CityRoam™ Cupsole High-Top Sneakers
$120.00
Men's Bradstreet Waterproof Chukka Shoes
GORE-TEX®
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Men's Bradstreet Waterproof Chukka Shoes
$140.00
Men's Adventure Cupsole Alpine Chukka Shoes
Wheat Nubuck
Black Full-Grain
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Men's Adventure Cupsole Alpine Chukka Shoes
$125.00 $99.99

20% off

Men's Davis Square Mixed-Media Chukka Shoes
Black Nubuck/Cordura® Canvas
Navy Nubuck
Black Nubuck/Cordura® Canvas
Medium Grey Nubuck
Wheat Nubuck/Cordura® Canvas
Black Nubuck/Cordura® Canvas
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Men's Davis Square Mixed-Media Chukka Shoes
$80.00
Men's CityRoam™ Cupsole Chukka Shoes
Olive Full-Grain
Brown Full-Grain
Wheat Full-Grain
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Men's CityRoam™ Cupsole Chukka Shoes
$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 NXTWool™ Chukka Boots
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Men's FlyRoam NXTWool™ Chukka Boots
$180.00
Men's Killington Hiker Chukka Boots
Navy Nubuck
Dark Grey Nubuck
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Men's Killington Hiker Chukka Boots
$130.00
Men's Brook Park Lightweight Chukka Shoes
Dark Brown Full-Grain
Black Full-Grain
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Men's Brook Park Lightweight Chukka Shoes
$130.00 $99.99

23% off

Men's FlyRoam™ Leather Sneaker Boots
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Men's FlyRoam™ Leather Sneaker Boots
$140.00
Men's 45th Anniversary Adventure Cupsole Chukka Shoes
Dark Green Full-Grain
Brown Full-Grain
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Men's 45th Anniversary Adventure Cupsole Chukka Shoes
$120.00
Men's 45th Anniversary Adventure Cupsole Chukka Shoes
Brown Full-Grain
Dark Green Full-Grain
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Men's 45th Anniversary Adventure Cupsole Chukka Shoes
$120.00
Men's 45th Anniversary Adventure Cupsole Chukka Shoes
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Men's 45th Anniversary Adventure Cupsole Chukka Shoes
$120.00
Men's 45th Anniversary 6-Inch Premium Chelsea Boots
Green Full-Grain
Brown Nubuck
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Men's 45th Anniversary 6-Inch Premium Chelsea Boots
$180.00
Men's 45th Anniversary 6-Inch Premium Chelsea Boots
Brown Nubuck
Green Full-Grain
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Men's 45th Anniversary 6-Inch Premium Chelsea Boots
$180.00
Men's CityRoam™ Cupsole Chukka Shoes
Brown Full-Grain
Olive Full-Grain
Wheat Full-Grain
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Men's CityRoam™ Cupsole Chukka Shoes
$140.00
Men's Davis Square Mixed-Media Chukka Shoes
Black Nubuck/Cordura® Canvas
Navy Nubuck
Black Nubuck/Cordura® Canvas
Medium Grey Nubuck
Wheat Nubuck/Cordura® Canvas
Black Nubuck/Cordura® Canvas
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Men's Davis Square Mixed-Media Chukka Shoes
$80.00
Men's Cross Mark Waterproof Chukka Shoes
Wheat Nubuck
Dark Brown Full-Grain
GORE-TEX®
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Men's Cross Mark Waterproof Chukka Shoes
$160.00
Men's CityRoam™ Cupsole Chukka Shoes
Wheat Full-Grain
Olive Full-Grain
Brown Full-Grain
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Men's CityRoam™ Cupsole Chukka Shoes
$140.00
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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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The Original Yellow Boot ™
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