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Outdoor Mens Chukka Boots

Rockport Rugged Bucks Waterproof Boot (Men's)
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Rockport Rugged Bucks Waterproof Boot(Men's) -Boston Tan
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Rockport Rugged Bucks Waterproof Boot(Men's) -New Black Leather
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Rockport Rugged Bucks Waterproof Boot(Men's) -Tan Full Grain Leather
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$100.00
$120.00 17% 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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$54.95
$80.00 31% off
Timberland Davis Square Plain Toe Chukka Boot (Men's)
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Timberland Davis Square Plain Toe Chukka Boot(Men's) -Black Iris Nubuck/Cordura® EcoMade Fiber
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$59.95
$90.00 33% 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
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$129.99
$150.00 13% off
Timberland Killington Chukka Boot (Men's)
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Timberland Killington Chukka Boot(Men's) -Black Leather
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$79.95
$125.00 36% off
Keen Grayson Chukka Boot (Men's)
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Keen Grayson Chukka Boot(Men's) -Mid Brown/Scylum
Keen Grayson Chukka Boot(Men's) -Sage/Lama
$129.95
Timberland Groveton Leather and Fabric Chukka Boot (Men's)
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Timberland Groveton Leather and Fabric Chukka Boot(Men's) -Wheat Nubuck/Canvas
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$54.95
$80.00 31% off
Timberland Premium Chukka (Men's)
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Timberland Premium Chukka(Men's) -Wheat Nubuck
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$84.95
$145.00 41% off
Chaco Thompson Chukka Boot (Men's)
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Chaco Thompson Chukka Boot(Men's) -Dark Gull Gray Nubuck/Full Grain Leather
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Chaco Thompson Chukka Boot(Men's) -Pinecone Nubuck/Full Grain Leather
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$104.95
$135.00 22% off
Reef Voyage Boot LE (Men's)
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Reef Voyage Boot LE(Men's) -Brown
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Reef Voyage Boot LE(Men's) -Chocolate
$115.99 - $144.95
$145.00 up to 20% off
Timberland Earthkeepers Brook Park Chukka (Men's)
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Timberland Earthkeepers Brook Park Chukka(Men's) -Black Smooth
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$104.95
$130.00 19% off
Reef Voyage Chukka Boot (Men's)
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Reef Voyage Chukka Boot(Men's) -Bungee
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Reef Voyage Chukka Boot(Men's) -Black/Natural
$103.99 - $129.95
$130.00 up to 20% off