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Timberland rightfully has earned a rock-solid reputation for boots, shoes and other premium products with a refined sense of rugged. Pioneers in the...

Timberland

Timberland Chukka Boots

Timberland Kendrick Chukka Boot (Men's)
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Timberland Kendrick Chukka Boot(Men's) -Black Full Grain Leather
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Timberland Kendrick Chukka Boot(Men's) -Medium Brown Full Grain Leather
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$94.95
$140.00 32% off
Timberland Squall Canyon WingTip Chukka Waterproof Boot (Men's)
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Timberland Squall Canyon WingTip Chukka Waterproof Boot(Men's) -Dark Brown Full Grain Leather
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Timberland Squall Canyon WingTip Chukka Waterproof Boot(Men's) -Dark Green Suede
Sale
$99.95
$150.00 33% off
Timberland Bardstown Plain Toe Chukka Boot (Men's)
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Timberland Bardstown Plain Toe Chukka Boot(Men's) -Black Full Grain Leather
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Timberland Bardstown Plain Toe Chukka Boot(Men's) -Medium Brown Full Grain Leather
Sale
$179.95
$300.00 40% off
Timberland Premium Chukka (Men's)
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Timberland Premium Chukka(Men's) -Wheat Nubuck
Sale
$101.95
$145.00 30% off
Timberland Davis Square Fabric/Leather Chukka Boot (Men's)
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Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Black Nubuck/Cordura® EcoMade Fiber
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Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Medium Grey Nubuck/Cordura® Fiber
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Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Navy Nubuck/Cordura® Fiber
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Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Blackout Nubuck/Cordura® EcoMade Fiber
$54.95 - $59.95
$80.00 up to 31% off
Timberland Killington Chukka Boot (Men's)
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Timberland Killington Chukka Boot(Men's) -Black Leather
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Timberland Killington Chukka Boot(Men's) -Medium Brown Full Grain Leather/Mesh
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$79.95 - $99.95
$125.00 up to 36% off
Timberland FlyRoam Go Lace Chukka Boot (Women's)
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Timberland FlyRoam Go Lace Chukka Boot(Women's) -Jet Black Escape/Natural Sandune
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Timberland FlyRoam Go Lace Chukka Boot(Women's) -Pure Cashmere Escape/Natural Sandune
Sale
$94.99
$120.00 21% off
Timberland Davis Square Plain Toe Chukka Boot (Men's)
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Timberland Davis Square Plain Toe Chukka Boot(Men's) -Pomegranate Nubuck/Cordura® Fiber
Sale
$49.95
$80.00 38% off
Timberland Classic TBL® Chukka (Men's)
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Timberland Classic TBL® Chukka(Men's) -Wheat Nubuck Leather
Sale
$84.95
$135.00 37% off
Timberland Earthkeepers Brook Park Chukka (Men's)
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Timberland Earthkeepers Brook Park Chukka(Men's) -Black Smooth
Sale
$104.95
$130.00 19% off
Timberland Carter Notch Plain Toe Waterproof Chukka Boot (Men's)
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Timberland Carter Notch Plain Toe Waterproof Chukka Boot(Men's) -Black Riptide Galloper Full Grain Leather
Sale
$111.99
$140.00 20% off
Timberland Britton Hill Clean Chukka Boot (Men's)
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Timberland Britton Hill Clean Chukka Boot(Men's) -Black Full Grain Leather
Sale
$129.99
$150.00 13% off