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Men's Port Union Waterproof Chukka Boots
Rust Nubuck
Black Full-Grain
Men's Port Union Waterproof Chukka Boots
$165.00
Men's Kendrick Waterproof Chukka Boots
Dark Brown Full-Grain
Black Full-Grain
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EXTRA 25% OFF- IN CART
Men's Kendrick Waterproof Chukka Boots
$160.00
Men's Oakrock Chukka Boots
Black Full-Grain
Brown Full-Grain
Men's Oakrock Chukka Boots
$140.00
Men's CityRoam™ Cupsole Chukka Shoes
Wheat Full-Grain
Olive Full-Grain
Brown Full-Grain
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
EXTRA 25% OFF- IN CART
Men's CityRoam™ Cupsole Chukka Shoes
$140.00
Men's City's Edge Waterproof Chukka Boots
Black Full-Grain
Dark Brown Full-Grain
GORE-TEX®
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EXTRA 25% OFF- IN CART
Men's City's Edge Waterproof Chukka Boots
$160.00
Men's CityRoam™ Cupsole Chukka Shoes
Olive Full-Grain
Brown Full-Grain
Wheat Full-Grain
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
EXTRA 25% OFF- IN CART
Men's CityRoam™ Cupsole Chukka Shoes
$140.00
Men's City's Edge Waterproof Chukka Boots
Dark Brown Full-Grain
Black Full-Grain
GORE-TEX®
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
EXTRA 25% OFF- IN CART
Men's City's Edge Waterproof Chukka Boots
$160.00
Men's Port Union Waterproof Chukka Boots
Black Full-Grain
Rust Nubuck
Men's Port Union Waterproof Chukka Boots
$165.00
Men's Timberland® Waterproof Chukka Boots
GORE-TEX®
Men's Timberland® Waterproof Chukka Boots
$155.00
Men's Killington Leather Chukka Sneaker Boots
Wheat Nubuck
Navy Nubuck
Black Nubuck
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EXTRA 25% OFF- IN CART
Men's Killington Leather Chukka Sneaker Boots
$125.00
Men's Squall Canyon Waterproof D-Ring Chukka Boots
Brown Full-Grain
Dark Brown Full-Grain
Olive Full-Grain
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EXTRA 25% OFF- IN CART
Men's Squall Canyon Waterproof D-Ring Chukka Boots
$165.00
Men's Squall Canyon Waterproof Moc-Toe Chukka Boots
Black Full-Grain
Brown Full-Grain
Men's Squall Canyon Waterproof Moc-Toe Chukka Boots
$150.00
Men's Classic Waterproof Chukka Boots
Wheat Nubuck
Black Smooth
Men's Classic Waterproof Chukka Boots
$135.00
Men's Groveton Chukka Shoes
Men's Groveton Chukka Shoes
$80.00
Men's Newtonbrook Moc-Toe Chukka Boots
Black Nubuck
Wheat Nubuck
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EXTRA 25% OFF- IN CART
Men's Newtonbrook Moc-Toe Chukka Boots
$110.00
Men's Mt. Maddsen Waterproof Chukka Boots
Black Full-Grain
Dark Brown Full-Grain
Men's Mt. Maddsen Waterproof Chukka Boots
$120.00
Men's Mt. Maddsen Waterproof Chukka Boots
Dark Brown Full-Grain
Black Full-Grain
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EXTRA 25% OFF- IN CART
Men's Mt. Maddsen Waterproof Chukka Boots
$120.00
Men's Adventure Cupsole Chukka Shoes
Burnished Wheat Nubuck
Olive Full-Grain
Medium Brown Full-Grain
Black Nubuck
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
EXTRA 25% OFF- IN CART
Men's Adventure Cupsole Chukka Shoes
$120.00
Men's TBL® 1973 Newman Waterproof Chukka Boots
Black Nubuck
Rust Full-Grain
Wheat Nubuck
Men's TBL® 1973 Newman Waterproof Chukka Boots
$160.00
Men's Oakrock Chukka Boots
Brown Full-Grain
Black Full-Grain
Men's Oakrock Chukka Boots
$140.00
Men's CityRoam™ Cupsole Chukka Shoes
Black Full-Grain
Blackout Nubuck
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
EXTRA 25% OFF- IN CART
Men's CityRoam™ Cupsole Chukka Shoes
$140.00
Men's CityRoam™ Cupsole Chukka Shoes
Blackout Nubuck
Black Full-Grain
[ES_PRODUCT_GRID_PROMOTION_MESSAGE]
EXTRA 25% OFF- IN CART
Men's CityRoam™ Cupsole Chukka Shoes
$140.00
Men's Squall Canyon Waterproof Chukka Boots
Black Full-Grain
Brown Full-Grain
Olive Full-Grain
Men's Squall Canyon Waterproof Chukka Boots
$150.00
Men's Squall Canyon Waterproof Chukka Boots
Brown Full-Grain
Black Full-Grain
Olive Full-Grain
Men's Squall Canyon Waterproof Chukka 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.