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$150 - $300 Mens Chukka Boots

UGG Neumel Waterproof Chukka Boot (Men's)
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Sale
UGG Neumel Waterproof Chukka Boot(Men's) -Black Full Grain Leather
UGG Neumel Waterproof Chukka Boot(Men's) -Charcoal Full Grain Leather
UGG Neumel Waterproof Chukka Boot(Men's) -Grizzly Full Grain Leather
$114.95 - $179.95
$180.00 up to 36% off
Timberland Bardstown Plain Toe Chukka Boot (Men's)
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Sale
Timberland Bardstown Plain Toe Chukka Boot(Men's) -Black Full Grain Leather
Sale
Timberland Bardstown Plain Toe Chukka Boot(Men's) -Medium Brown Full Grain Leather
Sale
$179.95
$300.00 40% off
Naot Pilot (Men's)
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Naot Pilot(Men's) -Brown Gradient Handcrafted Leather
Naot Pilot(Men's) -Desert Suede
Naot Pilot(Men's) -Gray Suede
Naot Pilot(Men's) -Oily Coal Nubuck
Naot Pilot(Men's) -Seal Brown Suede
Naot Pilot(Men's) -Vintage Grey Leather
$239.95
UGG Avalanche Neumel Ankle Boot (Men's)
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Sale
UGG Avalanche Neumel Ankle Boot(Men's) -Desert Tan Suede
Sale
UGG Avalanche Neumel Ankle Boot(Men's) -Chestnut Suede
UGG Avalanche Neumel Ankle Boot(Men's) -True Navy Suede
$219.95 - $274.95
$275.00 up to 20% off
Cole Haan Colton Chukka Boot (Men's)
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Cole Haan Colton Chukka Boot(Men's) -Copper/Peacoat Leather
Sale
$169.95
$250.00 32% off
UGG Dagmann Chukka Boot (Men's)
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Sale
UGG Dagmann Chukka Boot(Men's) -Black/Tan Trim Full Grain Leather
UGG Dagmann Chukka Boot(Men's) -Grizzly Full Grain Leather
$147.95 - $199.95
$200.00 up to 26% off
Cole Haan Wagner Grand Apron Chukka Boot (Men's)
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Cole Haan Wagner Grand Apron Chukka Boot(Men's) -Java Nubuck Waterproof Leather
Sale
$239.99
$280.00 14% off
Vionic Chase Chukka Boot (Men's)
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Sale
Vionic Chase Chukka Boot(Men's) -Black Suede
Vionic Chase Chukka Boot(Men's) -Tan Suede
$159.95
ara Ethan 28803 Chukka Boot (Men's)
New!
Sale
ara Ethan 28803 Chukka Boot(Men's) -Black Suede
Sale
ara Ethan 28803 Chukka Boot(Men's) -Brown Suede
Sale
ara Ethan 28803 Chukka Boot(Men's) -Stone Grey Suede
Sale
$164.95
$199.00 17% off
Drew Keith (Men's)
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Sale
Drew Keith(Men's) -Black Leather
Sale
Drew Keith(Men's) -Brandy Leather
Sale
$178.18
$190.00 6% off
Cole Haan Original Grand Chukka Boot (Men's)
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Sale
Cole Haan Original Grand Chukka Boot(Men's) -Woodbury Leather/Ivory
Sale
$149.99 - $152.95
$180.00 up to 15% off
Pikolinos Salou Chukka Boot M9M-8148 (Men's)
New!
Sale
Pikolinos Salou Chukka Boot M9M-8148(Men's) -Black Leather
Sale
Pikolinos Salou Chukka Boot M9M-8148(Men's) -Olmo Leather
Sale
$169.95
$200.00 15% off
Pikolinos Chile 01G-5056 (Men's)
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Sale
Pikolinos Chile 01G-5056(Men's) -Black
Pikolinos Chile 01G-5056(Men's) -Cuero
Pikolinos Chile 01G-5056(Men's) -Olmo
$170.00 - $179.95
ECCO Turn GORE-TEX Boot (Men's)
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ECCO Turn GORE-TEX Boot(Men's) -Coffee Lexi Leather
Sale
ECCO Turn GORE-TEX Boot(Men's) -Mocha Oil Nubuck
Sale
$206.95
$230.00 10% off
Pikolinos Glasgow 05M-6030F (Men's)
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Pikolinos Glasgow 05M-6030F(Men's) -Choco/Cuero Leather
Pikolinos Glasgow 05M-6030F(Men's) -Ron/Grey
$195.00 - $199.95
Bruno Magli Palermo Boot (Men's)
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Sale
Bruno Magli Palermo Boot(Men's) -Dark Brown Leather
Sale
$201.95
$500.00 60% off
Dr. Martens Ramsey Chukka Boot
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Sale
Dr. Martens Ramsey Chukka Boot -Black Polished Smooth/Friesian Hair On
$159.95
Bruno Magli Chavez Italian Suede Chukka Boot (Men's)
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Sale
Bruno Magli Chavez Italian Suede Chukka Boot(Men's) -Cognac Suede
Sale
$183.95
$450.00 59% off
ECCO Melbourne Chukka Boot (Men's)
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Sale
ECCO Melbourne Chukka Boot(Men's) -Black Full Grain Leather
ECCO Melbourne Chukka Boot(Men's) -Cocoa Brown Full Grain Leather
$169.95
UGG Cali Chukka Sneaker (Men's)
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Sale
UGG Cali Chukka Sneaker(Men's) -Antelope Suede
UGG Cali Chukka Sneaker(Men's) -Chestnut Suede
UGG Cali Chukka Sneaker(Men's) -Seal Suede
$135.95 - $179.95
$180.00 up to 24% off
Frye Murray Chukka Boot (Men's)
New!
Sale
Frye Murray Chukka Boot(Men's) -Cognac Leather
Sale
Frye Murray Chukka Boot(Men's) -Grey Leather
Sale
$213.95 - $267.99
$298.00 up to 28% off