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Discount Mens Chukka Boots

Clarks Bushacre 2 Boot (Men's)
New!
Sale
Clarks Bushacre 2 Boot(Men's) -Beeswax Leather
Sale
Clarks Bushacre 2 Boot(Men's) -Black Leather
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Clarks Bushacre 2 Boot(Men's) -Black Suede
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Clarks Bushacre 2 Boot(Men's) -Black Waxy Leather
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Clarks Bushacre 2 Boot(Men's) -Dark Brown Leather
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Clarks Bushacre 2 Boot(Men's) -Dark Olive Leather
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Clarks Bushacre 2 Boot(Men's) -Dark Tan Leather
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Clarks Bushacre 2 Boot(Men's) -Grey Leather
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Clarks Bushacre 2 Boot(Men's) -Grey Suede
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Clarks Bushacre 2 Boot(Men's) -Navy Leather
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Clarks Bushacre 2 Boot(Men's) -Wheat Suede
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Clarks Bushacre 2 Boot(Men's) -Wine Leather
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$54.99 - $87.45
$100.00 up to 45% off
Rockport Essential Details Waterproof Chukka Boot (Men's)
New!
Sale
Rockport Essential Details Waterproof Chukka Boot(Men's) -Black Full Grain Leather
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$109.95
$125.00 12% off
Clarks Stinson Hi Moc Toe Boot (Men's)
New!
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Clarks Stinson Hi Moc Toe Boot(Men's) -Beeswax Leather
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Clarks Stinson Hi Moc Toe Boot(Men's) -Black Oily Leather
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Clarks Stinson Hi Moc Toe Boot(Men's) -Brown Oily Leather
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Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Olive Leather
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Clarks Stinson Hi Moc Toe Boot(Men's) -Sand Suede
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$89.99 - $98.99
$100.00 - $110.00 up to 10% off
Steve Madden Harken Chukka Boot (Men's)
New!
Sale
Steve Madden Harken Chukka Boot(Men's) -Black  Leather
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Steve Madden Harken Chukka Boot(Men's) -Cognac Leather
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$79.95
$90.00 11% off
Clarks Desert Boot (Men's)
New!
Sale
Clarks Desert Boot(Men's) -Beeswax Full Grain Leather
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Clarks Desert Boot(Men's) -Black/Black Suede
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Clarks Desert Boot(Men's) -Blue/Grey Suede
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Clarks Desert Boot(Men's) -Brown/Brown Suede
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Clarks Desert Boot(Men's) -Mahogany Suede
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Clarks Desert Boot(Men's) -Navy Canvas
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Clarks Desert Boot(Men's) -Oak Suede
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Clarks Desert Boot(Men's) -Taupe Canvas
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$96.99 - $129.95
$130.00 - $140.00 up to 31% off
Clarks Hinman Mid Chukka Boot (Men's)
New!
Sale
Clarks Hinman Mid Chukka Boot(Men's) -Black Leather
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Clarks Hinman Mid Chukka Boot(Men's) -Dark Tan Suede
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Clarks Hinman Mid Chukka Boot(Men's) -Mahogany Leather
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$89.99
$100.00 10% off
Ariat Spitfire Chukka Boot (Men's)
New!
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Ariat Spitfire Chukka Boot(Men's) -Brown Bomber Full Grain Leather
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$99.95 - $109.95
$99.95 - $109.95 up to 9% off
Timberland Killington Chukka Boot (Men's)
New!
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Timberland Killington Chukka Boot(Men's) -Black Leather
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$99.95
$125.00 20% off
Dr. Martens Work Sussex 3 Eye Chukka (Men's)
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Dr. Martens Work Sussex 3 Eye Chukka(Men's) -Black Bear Track
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Dr. Martens Work Sussex 3 Eye Chukka(Men's) -Dark Brown Bear Track
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$84.98
$95.00 11% off
Steve Madden Hestonn (Men's)
New!
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Steve Madden Hestonn(Men's) -Tan Leather
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$79.95
$90.00 11% off
Nunn Bush Lancaster Chukka Boot (Men's)
New!
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Nunn Bush Lancaster Chukka Boot(Men's) -Black Oiled Leather
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Nunn Bush Lancaster Chukka Boot(Men's) -Brown Oiled Leather
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Nunn Bush Lancaster Chukka Boot(Men's) -Camel Suede
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$63.95
$80.00 20% off
Twisted X Boots MDM0059 Driving Mocs Chukka Boot (Men's)
New!
Sale
Twisted X Boots MDM0059 Driving Mocs Chukka Boot(Men's) -Brown/Brown Print Leather
Sale
$99.95
$114.99 13% off
Clarks Wallabee (Men's)
New!
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Clarks Wallabee(Men's) -Black/Black Leather
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$139.95
$140.00 - $160.00 up to 13% off
Nunn Bush Galloway Chukka Boot (Men's)
New!
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Nunn Bush Galloway Chukka Boot(Men's) -Beige Suede
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Nunn Bush Galloway Chukka Boot(Men's) -Dark Brown Suede
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$63.95
$80.00 20% off
Rockport Charson Lace Up Ankle Boot (Men's)
New!
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Rockport Charson Lace Up Ankle Boot(Men's) -Black Leather
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Rockport Charson Lace Up Ankle Boot(Men's) -Dark Brown Leather
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$99.95
$140.00 29% off
UGG Neumel Boot (Men's)
New!
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UGG Neumel Boot(Men's) -Redwood
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$95.95 - $149.95
$130.00 - $150.00 up to 36% off
Florsheim Montinaro Chukka Boot (Men's)
New!
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Florsheim Montinaro Chukka Boot(Men's) -Saddle Tan Smooth Leather
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Florsheim Montinaro Chukka Boot(Men's) -Black Smooth Leather
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$99.95
$110.00 9% off
Lugz Mantle Mid Chukka Work Boot (Men's)
New!
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Lugz Mantle Mid Chukka Work Boot(Men's) -Black Synthetic
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Lugz Mantle Mid Chukka Work Boot(Men's) -Golden Wheat/Tan-Khaki/Gum Synthetic
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$43.99
$54.99 20% off
Clarks Stinson Lo (Men's)
New!
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Clarks Stinson Lo(Men's) -Beeswax Leather
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Clarks Stinson Lo(Men's) -Black Leather
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$89.99
$100.00 10% off
Clarks Tilden Top Chukka Boot (Men's)
New!
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Clarks Tilden Top Chukka Boot(Men's) -Black Full Grain Leather
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$102.99
$115.00 10% off
Clarks Desert Trek (Men's)
New!
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Clarks Desert Trek(Men's) -Chestnut Leather
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$119.99 - $139.95
$140.00 up to 14% off
Rockport Classic Break Chukka Boot (Men's)
New!
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Rockport Classic Break Chukka Boot(Men's) -Dark Brown Leather
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$106.45
$120.00 11% off
Ariat Edge LTE Moc H2O Composite Toe Chukka Boot (Men's)
New!
Sale
Ariat Edge LTE Moc H2O Composite Toe Chukka Boot(Men's) -Dark Brown Leather
Sale
$139.95
$149.95 7% off
UGG Neumel Ripstop Chukka Boot (Men's)
New!
Sale
UGG Neumel Ripstop Chukka Boot(Men's) -Charcoal Ripstop Nylon/Suede
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UGG Neumel Ripstop Chukka Boot(Men's) -True Navy Ripstop Nylon/Suede
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$64.95
$100.00 35% off
Twisted X Boots MDM0057 Driving Moc Chukka (Men's)
New!
Sale
Twisted X Boots MDM0057 Driving Moc Chukka(Men's) -Oiled Saddle/Blue Leather
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$104.95
$114.99 9% off
Stacy Adams Beckett Cap Toe Chukka Boot 24984 (Men's)
New!
Sale
Stacy Adams Beckett Cap Toe Chukka Boot 24984(Men's) -Brown Leather
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$84.95
$105.00 19% off
Lugz Breech Wallaby Work Boot (Men's)
New!
Sale
Lugz Breech Wallaby Work Boot(Men's) -Charcoal/Dark Charcoal/Grey Thermabuck
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Lugz Breech Wallaby Work Boot(Men's) -Golden Wheat/Bark/Cream/Gum Thermabuck
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$44.99
$89.99 50% off
Florsheim Castellano Chukka (Men's)
New!
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Florsheim Castellano Chukka(Men's) -Black Leather
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Florsheim Castellano Chukka(Men's) -Brown Leather
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$109.95
$140.00 21% off
Timberland Earthkeepers Brook Park Chukka (Men's)
New!
Sale
Timberland Earthkeepers Brook Park Chukka(Men's) -Black Smooth
Sale
$104.95
$130.00 19% off
Ariat Edge LTE Moc Composite Toe Chukka Boot (Men's)
New!
Sale
Ariat Edge LTE Moc Composite Toe Chukka Boot(Men's) -Dark Brown Leather
Sale
$119.95
$129.95 8% off
Wolverine Bedford Soft Toe Chukka Boot (Men's)
New!
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Wolverine Bedford Soft Toe Chukka Boot(Men's) -Black Full Grain Leather
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Wolverine Bedford Soft Toe Chukka Boot(Men's) -Brown Full Grain Leather
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$104.99
$115.00 9% off
Dr. Scholl's Roundabout Chukka Boot (Men's)
New!
Sale
Dr. Scholl's Roundabout Chukka Boot(Men's) -Dark Brown Fabric/Faux Leather
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$59.95
$100.00 40% off
Clarks Atticus Limit Chukka Boot (Men's)
New!
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Clarks Atticus Limit Chukka Boot(Men's) -Navy Nubuck
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Clarks Atticus Limit Chukka Boot(Men's) -Taupe Nubuck
Sale
$94.45 - $134.95
$135.00 up to 30% off
Cole Haan GrandPro Chukka Sneaker (Men's)
New!
Sale
Cole Haan GrandPro Chukka Sneaker(Men's) -Black Leather
Sale
$112.95
$150.00 25% off
Deer Stags Seattle Boot (Men's)
New!
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Deer Stags Seattle Boot(Men's) -Black
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Deer Stags Seattle Boot(Men's) -Luggage
Sale
$59.99
$80.00 25% off
Florsheim NDNS Chukka Boot (Men's)
New!
Sale
Florsheim NDNS Chukka Boot(Men's) -Black Leather
Sale
$97.95
$130.00 25% off