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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 Waterproof Chukka Boots
Dark Brown Full-Grain
Black Full-Grain
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Men's Kendrick Waterproof Chukka Boots
$160.00
Men's Davis Square Mixed-Media Chukka Shoes
Medium Grey Nubuck
Navy Nubuck
Black Nubuck/Cordura® Canvas
Black Nubuck/Cordura® Canvas
Wheat Nubuck/Cordura® Canvas
Black Nubuck/Cordura® Canvas
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Men's Davis Square Mixed-Media Chukka Shoes
$80.00
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 Adventure Cupsole Waterproof Chukka Shoes
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Men's Adventure Cupsole Waterproof Chukka Shoes
$170.00
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 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 Killington Hiker Chukka Boots
Navy Nubuck
Dark Grey Nubuck
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Men's Killington Hiker Chukka Boots
$130.00
Men's CityRoam™ Cupsole High-Top Sneakers
Beige Nubuck/Canvas
Black Nubuck/Canvas
Olive Green Nubuck/Canvas
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Men's CityRoam™ Cupsole High-Top Sneakers
$120.00
Men's FlyRoam™ Leather Sneaker Boots
Dark Brown Nubuck
Black Full-Grain
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Men's FlyRoam™ Leather Sneaker Boots
$140.00
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 Adventure Cupsole Alpine Chukka Shoes
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Men's Adventure Cupsole Alpine Chukka Shoes
$125.00
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
Men's Cross Mark Waterproof Chukka Shoes
Wheat Nubuck
Dark Brown Full-Grain
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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
Men's Cross Mark Chukka Shoes
Dark Grey Full-Grain
Brown Nubuck
Wheat Nubuck
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Men's Cross Mark Chukka Shoes
$125.00
Men's City's Edge Waterproof Chukka Boots
Dark Brown Full-Grain
Black Full-Grain
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Men's City's Edge Waterproof Chukka Boots
$160.00
Men's City's Edge Suede Waterproof Chukka Boots
Dark Grey Suede
Dark Brown Suede
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Men's City's Edge Suede Waterproof Chukka Boots
$120.00
Men's City's Edge Suede Waterproof Chukka Boots
Dark Brown Suede
Dark Grey Suede
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Men's City's Edge Suede Waterproof Chukka Boots
$120.00
Men's Squall Canyon Waterproof Chukka Boots
Dark Green Suede
Black Full-Grain
Dark Brown Full-Grain
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Men's Squall Canyon Waterproof Chukka Boots
$150.00
Men's Radford Chelsea Boots
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Men's Radford Chelsea Boots
$150.00
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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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