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Men's Redwood Falls Waterproof Chukkas
Wheat Full-Grain
Brown Full-Grain
Black Full-Grain
Men's Redwood Falls Waterproof Chukkas
$130.00
Men's Oakrock Waterproof Chukka Boots
Men's Oakrock Waterproof Chukka Boots
$150.00
Men's Stormbuck Waterproof Chukka Shoes
Men's Stormbuck Waterproof Chukka Shoes
$150.00
Men's Davis Square Mixed-Media Chukka Shoes
Medium Grey Nubuck
Grey Nubuck/Blue
Black Nubuck
Navy Nubuck
Black Nubuck/Cordura® Canvas
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
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 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
Black Full-Grain
Dark Brown Full-Grain
Men's Kendrick Waterproof Chukka Boots
$160.00
Men's Squall Canyon Waterproof Chukka Boots
Men's Squall Canyon Waterproof Chukka Boots
$150.00
Men's Yorkdale Chukka Boots
Rust Full-Grain
Black Full-Grain
Men's Yorkdale Chukka Boots
$110.00
Men's Classic Waterproof Chukka Boots
Black Smooth
Wheat Nubuck
Dark Brown Smooth
Men's Classic Waterproof Chukka Boots
$135.00
Men's Classic Waterproof Chukka Boots
Wheat Nubuck
Black Smooth
Dark Brown Smooth
Men's Classic Waterproof Chukka Boots
$135.00
Men's Timberland® Icon Waterproof Chukka Boots
Wheat Nubuck
Black Nubuck
Men's Timberland® Icon Waterproof Chukka Boots
$160.00
Men's Davis Square Waterproof Chukkas
Wheat Nubuck
Black Nubuck
Men's Davis Square Waterproof Chukkas
$120.00
Men's Davis Square Waterproof Chukkas
Black Nubuck
Wheat Nubuck
Men's Davis Square Waterproof Chukkas
$120.00
Men's Cross Mark Waterproof Chukkas with GORE-TEX Fabric
Medium Brown Full-Grain
Wheat Nubuck
Men's Cross Mark Waterproof Chukkas with GORE-TEX Fabric
$160.00
Men's Tenmile Chukka Boots
Men's Tenmile Chukka Boots
$110.00
Men's Mt. Maddsen Waterproof Chukka Boots
Men's Mt. Maddsen Waterproof Chukka Boots
$120.00
Tenmile Chukka Boots
Tenmile Chukka Boots
$110.00
Men's CityRoam™ Cupsole Chukka Shoes
Wheat Full-Grain
Olive Full-Grain
Brown 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
Wheat Nubuck
Black Nubuck
Brown Full-Grain
Men's Bradstreet Leather Chukka Sneaker Boots
$120.00
Men's Cross Mark Waterproof Chukka Shoes
Wheat Nubuck
Medium Brown Full-Grain
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.