Man wearing Timberland Chukkas

Chukkas

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Men's Davis Square Mixed-Media Chukka Shoes
Wheat Nubuck/Green
Dark Green Nubuck
Grey Nubuck/Blue
Black Nubuck
Navy Nubuck
Medium Grey Nubuck
Black Nubuck/Cordura® Canvas
Wheat Nubuck
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EXTRA 40% OFF- IN CART
Men's Davis Square Mixed-Media Chukka Shoes
$85.00
Men's Davis Square Leather Collar Chukka Shoes
Black Nubuck/Cordura® Canvas
Wheat Nubuck/Cordura® Canvas
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EXTRA 40% OFF- IN CART
Men's Davis Square Leather Collar Chukka Shoes
$90.00
Men's Timberland Originals Chukka Boots
Dark Grey Nubuck
Rust Nubuck
Men's Timberland Originals Chukka Boots
$150.00
Men's Jackson's Landing Waterproof Chukka Boots
Black Nubuck
Rust Full-Grain
Dark Brown Full-Grain
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EXTRA 40% OFF- IN CART
Men's Jackson's Landing Waterproof Chukka Boots
$150.00 $119.99

20% off

Men's Oakrock Chukka Boots
Black Full-Grain
Brown Full-Grain
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Men's Oakrock Chukka Boots
$130.00
Men's Oakrock Chukka Boots
Brown Full-Grain
Black Full-Grain
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Men's Oakrock Chukka Boots
$130.00
Men's Port Union Waterproof Chukka Boots
Rust Nubuck
Black Full-Grain
Light Brown Nubuck
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EXTRA 40% OFF- IN CART
Men's Port Union Waterproof Chukka Boots
$165.00
Men's Kendrick Waterproof Chukka Boots
Black Full-Grain
Dark Brown Full-Grain
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EXTRA 40% OFF- IN CART
Men's Kendrick Waterproof Chukka Boots
$160.00
Men's Timberland Boot Company® Wodehouse Chukka Boots
Burnished Black
Burnished Dark Brown
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EXTRA 40% OFF- IN CART
Men's Timberland Boot Company® Wodehouse Chukka Boots
$300.00
Men's Squall Canyon Waterproof Chukka Boots
Black Full-Grain
Brown Full-Grain
Men's Squall Canyon Waterproof Chukka Boots
$150.00
Men's Yorkdale Chukka Boots
Rust Full-Grain
Black Full-Grain
Black Full-Grain
Rust Full-Grain
Men's Yorkdale Chukka Boots
$110.00
Men's Timberland® Waterproof Chukka Boots
Dark Brown Smooth
Black Smooth
Men's Timberland® Waterproof Chukka Boots
$135.00
Men's Timberland® Classic Waterproof Chukka Boots
Black Nubuck
Wheat Nubuck
Men's Timberland® Classic Waterproof Chukka Boots
$160.00
Men's Timberland® Waterproof Chukka Boots
GORE-TEX®
Men's Timberland® Waterproof Chukka Boots
$155.00
Men's Mt. Maddsen Waterproof Chukka Boots
Men's Mt. Maddsen Waterproof Chukka Boots
$120.00
Men's CityRoam™ Cupsole Chukka Shoes
Olive Full-Grain
Brown Full-Grain
Wheat Full-Grain
Men's CityRoam™ Cupsole Chukka Shoes
$140.00
Men's Killington Leather Chukka Sneaker Boots
Wheat Nubuck
Black Nubuck
Medium Grey Nubuck
Olive Nubuck
Men's Killington Leather Chukka Sneaker Boots
$125.00
Men's Bradstreet Leather Chukka Sneaker Boots
Brown Full-Grain
Black Nubuck
Wheat Nubuck
Men's Bradstreet Leather Chukka Sneaker Boots
$120.00
Men's Cross Mark Waterproof Chukka Shoes
GORE-TEX®
Men's Cross Mark Waterproof Chukka Shoes
$160.00
Men's Bradstreet Leather Chukka Sneaker Boots
Black Nubuck
Brown Full-Grain
Wheat Nubuck
Men's Bradstreet Leather Chukka Sneaker Boots
$120.00
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We have men's chukka boots for every occasion. Our men's boots are crafted with high quality materials using modern technology for durability and comfort. Finish the look with a pair of our pants or chinos for a tailored but casual look.