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Mens Leather Chukka Boots

Clarks Bushacre 2 Boot (Men's)
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Clarks Bushacre 2 Boot(Men's) -Beeswax Leather
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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) -Navy Leather
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Clarks Bushacre 2 Boot(Men's) -Taupe Distressed Suede
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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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Clarks Bushacre 2 Boot(Men's) -Brown Suede
$58.95 - $99.95
$100.00 up to 41% off
UGG Neumel Boot (Men's)
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UGG Neumel Boot(Men's) -Taupe Suede
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UGG Neumel Boot(Men's) -Black
UGG Neumel Boot(Men's) -Charcoal Suede
UGG Neumel Boot(Men's) -Chestnut Leather
UGG Neumel Boot(Men's) -Chestnut Two Tone Suede
UGG Neumel Boot(Men's) -Cordovan Cow Suede
UGG Neumel Boot(Men's) -Espresso Cow Suede
UGG Neumel Boot(Men's) -New Navy Suede
UGG Neumel Boot(Men's) -Salty Blue Suede
UGG Neumel Boot(Men's) -White Pepper Suede
$107.95 - $149.95
$130.00 - $150.00 up to 23% off
Clarks Stinson Hi Moc Toe Boot (Men's)
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Clarks Stinson Hi Moc Toe Boot(Men's) -Taupe Distressed Suede
New
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) -Black Suede
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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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Clarks Stinson Hi Moc Toe Boot(Men's) -Wheat Suede
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$24.95 - $109.95
$100.00 - $110.00 up to 75% off
Clarks Desert Boot (Men's)
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Clarks Desert Boot(Men's) -Sand/Sand Suede
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Clarks Desert Boot(Men's) -Bordeaux 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) -Olive/Olive Suede
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Clarks Desert Boot(Men's) -Taupe Canvas
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Clarks Desert Boot(Men's) -Beeswax Full Grain Leather
Clarks Desert Boot(Men's) -Black/Black Suede
Clarks Desert Boot(Men's) -Brown
Clarks Desert Boot(Men's) -Brown/Brown Suede
Clarks Desert Boot(Men's) -Oak Suede
$93.95 - $129.95
$130.00 - $140.00 up to 33% off
Rockport Charson Lace Up Ankle Boot (Men's)
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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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$120.00 - $130.00
$140.00 up to 14% off
Steve Madden Hestonn (Men's)
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Steve Madden Hestonn(Men's) -Tan Leather
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$79.95
$90.00 11% off
UGG Neumel Waterproof Chukka Boot (Men's)
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UGG Neumel Waterproof Chukka Boot(Men's) -True Navy Full Grain Leather
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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
ECCO Turn GORE-TEX Chukka Tie Boot (Men's)
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ECCO Turn GORE-TEX Chukka Tie Boot(Men's) -Mocha Cow Oil Nubuck
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ECCO Turn GORE-TEX Chukka Tie Boot(Men's) -Black Cow Oil Nubuck
ECCO Turn GORE-TEX Chukka Tie Boot(Men's) -Cocoa Brown Cow Oil Nubuck
$129.95 - $229.95
$170.00 - $230.00 up to 24% off
Dunham Johnson Chukka (Men's)
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Dunham Johnson Chukka(Men's) -Black Leather
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$111.95
$150.00 25% off
Rockport Sharp & Ready Chukka Boot (Men's)
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Rockport Sharp & Ready Chukka Boot(Men's) -Black Leather
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Rockport Sharp & Ready Chukka Boot(Men's) -Saddle Brown Leather
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Rockport Sharp & Ready Chukka Boot(Men's) -Brown/Brown Leather
Rockport Sharp & Ready Chukka Boot(Men's) -Castlerock Grey Leather
Rockport Sharp & Ready Chukka Boot(Men's) -Tobacco Suede
$116.99 - $155.00
$139.95 - $140.00 up to 16% 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
Timberland Premium Chukka (Men's)
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Timberland Premium Chukka(Men's) -Wheat Nubuck
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$101.95
$145.00 30% off
Clarks Desert Trek (Men's)
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Clarks Desert Trek(Men's) -Nut Brown Suede/Full Grain Leather
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Clarks Desert Trek(Men's) -Black/Black/Black Suede
$125.95 - $139.95
$140.00 up to 10% off
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) -Tan Full Grain Leather
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$100.00
$120.00 17% off
Steve Madden Harken Chukka Boot (Men's)
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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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$44.95 - $79.95
$90.00 up to 50% off
TOMS Chukka Boot Leather (Men's)
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TOMS Chukka Boot Leather(Men's) -Black Melange Woven
TOMS Chukka Boot Leather(Men's) -Brown Waterproof Pull Up Leather
$97.95 - $139.00
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
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$99.95
$150.00 33% off
Twisted X Boots MDM0061 Driving Mocs Chukka Boot (Men's)
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Twisted X Boots MDM0061 Driving Mocs Chukka Boot(Men's) -Tan/Tooled Flowers Leather
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$129.95
$139.99 7% 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
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$179.95
$300.00 40% off
Nunn Bush Lancaster Chukka Boot (Men's)
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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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$72.00
$80.00 10% off
Dunham Royalton Chukka (Men's)
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Dunham Royalton Chukka(Men's) -Brown Leather
Dunham Royalton Chukka(Men's) -Flagstone Leather
$149.95
Twisted X Boots MDM0059 Driving Mocs Chukka Boot (Men's)
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Twisted X Boots MDM0059 Driving Mocs Chukka Boot(Men's) -Brown/Brown Print Leather
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$99.95
$114.99 13% off
ECCO Jeremy Hybrid Chukka Boot (Men's)
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ECCO Jeremy Hybrid Chukka Boot(Men's) -Black/Black Nubuck Leather
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ECCO Jeremy Hybrid Chukka Boot(Men's) -Coffee Nubuck Leather
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$101.95 - $114.95
$150.00 up to 32% off
Ariat Spitfire Chukka Boot (Men's)
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Ariat Spitfire Chukka Boot(Men's) -Distressed Brown/Camo Full Grain Leather
New
Ariat Spitfire Chukka Boot(Men's) -Latigo Brown/Cortez Aztec Full Grain/Fabric
New
Ariat Spitfire Chukka Boot(Men's) -Aged Mahogany Leather
Ariat Spitfire Chukka Boot(Men's) -Brown Bomber Full Grain Leather
Ariat Spitfire Chukka Boot(Men's) -Brown Bomber Leather
Ariat Spitfire Chukka Boot(Men's) -Brown Bomber/Blue Laces Full Grain Leather
Ariat Spitfire Chukka Boot(Men's) -Wicker/Mustard Navajo Full Grain Leather/Fabric
New
$99.95 - $109.95
Clarks Stinson Lo (Men's)
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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
Vionic Chase Chukka Boot (Men's)
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Vionic Chase Chukka Boot(Men's) -Black Suede
Vionic Chase Chukka Boot(Men's) -Tan Suede
$159.95
Lucky Brand Mason Chukka Boot (Men's)
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Lucky Brand Mason Chukka Boot(Men's) -Black Leather
Lucky Brand Mason Chukka Boot(Men's) -British Tan Leather
Lucky Brand Mason Chukka Boot(Men's) -Cement Leather
Lucky Brand Mason Chukka Boot(Men's) -Chocolate Leather
$89.95 - $111.95
Nunn Bush Ozark Plain Toe Chukka Boot (Men's)
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Nunn Bush Ozark Plain Toe Chukka Boot(Men's) -Black Tumble Leather
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Nunn Bush Ozark Plain Toe Chukka Boot(Men's) -Brown Chamois Leather
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Nunn Bush Ozark Plain Toe Chukka Boot(Men's) -Rust Leather
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Nunn Bush Ozark Plain Toe Chukka Boot(Men's) -Tan Chamois Leather
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$76.00
$95.00 20% off