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    Discount Mens Casual Chukka Boots

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    Clarks Desert Trek (Men's)
    New!
    Sale
    Clarks Desert Trek(Men's) -Sand Suede
    Sale
    $119.00 - $139.95
    $140.00 up to 15% off
    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
    Sale
    Clarks Bushacre 2 Boot(Men's) -Black Waxy Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Brown Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Brown
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Brown Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Tan Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Grey Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Navy Leather
    Sale
    $59.99 - $99.95
    $100.00 up to 40% off
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Black Smooth
    Sale
    Clarks Desert Boot(Men's) -Burgundy Textile
    Sale
    Clarks Desert Boot(Men's) -Green Leather
    Sale
    Clarks Desert Boot(Men's) -Midnight
    Sale
    Clarks Desert Boot(Men's) -Natural Tan
    Sale
    Clarks Desert Boot(Men's) -Navy Tumbled Leather
    Sale
    Clarks Desert Boot(Men's) -Olive Suede
    Sale
    Clarks Desert Boot(Men's) -Tan Tumble
    Sale
    $69.95 - $204.00
    $130.00 - $240.00 up to 46% off
    Steve Madden Harken Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Cognac Leather
    Sale
    $84.95 - $89.95
    $90.00 up to 6% off
    Timberland Killington Chukka Boot (Men's)
    New!
    Sale
    Timberland Killington Chukka Boot(Men's) -Navy Full Grain Leather/Mesh
    Sale
    Timberland Killington Chukka Boot(Men's) -Navy Leather
    Sale
    $74.95 - $124.95
    $125.00 up to 40% off
    Clarks Stinson Hi Moc Toe Boot (Men's)
    New!
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Black Suede
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Black Waxy Leather
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Cranberry Leather
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Brown Leather
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Tan Leather
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Sand Suede
    Sale
    $80.95 - $109.95
    $100.00 - $110.00 up to 26% off
    Rockport Charson Lace Up Ankle Boot (Men's)
    New!
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Black Leather
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Dark Brown Leather
    Sale
    $94.95 - $139.95
    $140.00 up to 32% off
    Clarks Wallabee Boot (Men's)
    New!
    Sale
    Clarks Wallabee Boot(Men's) -Grey Suede
    Sale
    Clarks Wallabee Boot(Men's) -Slate Blue Suede
    Sale
    $127.50 - $139.95
    $140.00 - $150.00 up to 15% off
    Rockport Classic Break Chukka Boot (Men's)
    New!
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Catalina Leather
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Dark Bitter Chocolate Suede
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Dark Brown Leather
    Sale
    $92.45 - $134.95
    $135.00 up to 32% off
    Clarks Stratton Limit Boot (Men's)
    New!
    Sale
    Clarks Stratton Limit Boot(Men's) -Black Leather
    Sale
    Clarks Stratton Limit Boot(Men's) -Brown Leather
    Sale
    $119.95
    $135.00 11% off
    Clarks Clarkdale Jean Chukka Boot (Men's)
    New!
    Sale
    Clarks Clarkdale Jean Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    Clarks Clarkdale Jean Chukka Boot(Men's) -Dark Tan Full Grain Leather
    Sale
    $144.50
    $170.00 15% off
    Clarks Clarkdale Bara Chukka Boot (Men's)
    New!
    Sale
    Clarks Clarkdale Bara Chukka Boot(Men's) -Dark Tan Full Grain Leather
    Sale
    Clarks Clarkdale Bara Chukka Boot(Men's) -Olive Suede
    Sale
    $144.50
    $170.00 15% off
    Clarks Wallabee (Men's)
    New!
    Sale
    Clarks Wallabee(Men's) -Burgundy Suede
    Sale
    Clarks Wallabee(Men's) -Maple Suede
    Sale
    Clarks Wallabee(Men's) -Red Suede
    Sale
    $114.75 - $139.95
    $135.00 - $160.00 up to 15% off
    Rockport Rugged Bucks Waterproof Boot (Men's)
    New!
    Sale
    Rockport Rugged Bucks Waterproof Boot(Men's) -Castlerock Grey
    Sale
    $102.45 - $109.95
    $120.00 up to 15% off
    UGG Leighton Waterproof Chukka Boot (Men's)
    New!
    Sale
    UGG Leighton Waterproof Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    UGG Leighton Waterproof Chukka Boot(Men's) -Grizzly Full Grain Leather
    Sale
    UGG Leighton Waterproof Chukka Boot(Men's) -Slate Suede
    Sale
    $144.50 - $169.95
    $170.00 up to 15% off
    Clarks Hinman Mid Chukka Boot (Men's)
    New!
    Sale
    Clarks Hinman Mid Chukka Boot(Men's) -Black Leather
    Sale
    Clarks Hinman Mid Chukka Boot(Men's) -Dark Tan Suede
    Sale
    Clarks Hinman Mid Chukka Boot(Men's) -Mahogany Leather
    Sale
    $85.00
    $100.00 15% off
    Cole Haan Williams Welt Chukka II (Men's)
    New!
    Sale
    Cole Haan Williams Welt Chukka II(Men's) -Chestnut Burnish Leather/Suede
    Sale
    Cole Haan Williams Welt Chukka II(Men's) -Driftwood/Driftwood Suede
    Sale
    $159.95
    $250.00 36% off
    UGG Maksim Chukka Boot (Men's)
    New!
    Sale
    UGG Maksim Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    UGG Maksim Chukka Boot(Men's) -New Navy Suede
    Sale
    UGG Maksim Chukka Boot(Men's) -Stormy Seas Suede
    Sale
    UGG Maksim Chukka Boot(Men's) -Timeless Red Suede
    Sale
    $68.75 - $129.95
    $125.00 - $130.00 up to 45% off
    ECCO Turn GORE-TEX Chukka Tie Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Chukka Tie Boot(Men's) -Black Cow Oil Nubuck
    Sale
    $169.95 - $206.95
    $170.00 - $230.00 up to 10% off
    Nunn Bush Lancaster Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Lancaster Chukka Boot(Men's) -Black Oiled Leather
    Sale
    Nunn Bush Lancaster Chukka Boot(Men's) -Brown Oiled Leather
    Sale
    Nunn Bush Lancaster Chukka Boot(Men's) -Camel Suede
    Sale
    $56.00
    $80.00 30% off
    Rockport Essential Details Waterproof Chukka Boot (Men's)
    New!
    Sale
    Rockport Essential Details Waterproof Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    $99.95 - $109.95
    $110.00 up to 9% off
    Clarks Truxton Top Chukka Boot (Men's)
    New!
    Sale
    Clarks Truxton Top Chukka Boot(Men's) -Black Waterproof Cow Full Grain Leather
    Sale
    $105.95
    $115.00 8% off
    Altra Footwear Desert Chukka Boot (Men's)
    New!
    Sale
    Altra Footwear Desert Chukka Boot(Men's) -Blue/Lime
    Sale
    Altra Footwear Desert Chukka Boot(Men's) -Taupe
    Sale
    $83.95
    $120.00 30% off
    Clarks Un.Elott Mid Chukka Boot (Men's)
    New!
    Sale
    Clarks Un.Elott Mid Chukka Boot(Men's) -Black Cow Full Grain Leather
    Sale
    Clarks Un.Elott Mid Chukka Boot(Men's) -Burgundy Cow Full Grain Leather
    Sale
    $137.95
    $180.00 23% off
    Timberland Groveton Leather/Fabric Chukka (Men's)
    New!
    Sale
    Timberland Groveton Leather/Fabric Chukka(Men's) -Black Nubuck/Textile
    Sale
    $55.95 - $79.95
    $80.00 up to 30% off
    Bearpaw Spencer Chukka (Men's)
    New!
    Sale
    Bearpaw Spencer Chukka(Men's) -Black II Suede
    Sale
    Bearpaw Spencer Chukka(Men's) -Hickory II Suede
    Sale
    $59.99
    $69.99 14% off
    Dr. Martens Lea 4-Eye Chukka Boot (Men's)
    New!
    Sale
    Dr. Martens Lea 4-Eye Chukka Boot(Men's) -Tan/Biscuit Grizzly
    Sale
    $89.95 - $114.95
    $115.00 up to 22% off
    Cole Haan Grand Tour Chukka Boot (Men's)
    New!
    Sale
    Cole Haan Grand Tour Chukka Boot(Men's) -Black Leather/Cobblestone
    Sale
    Cole Haan Grand Tour Chukka Boot(Men's) -Midnight Grey Suede/Magnet
    Sale
    $101.95 - $119.95
    $170.00 - $280.00 up to 57% off
    Clarks Broyd Mid Chukka Boot (Men's)
    New!
    Sale
    Clarks Broyd Mid Chukka Boot(Men's) -Black Leather
    Sale
    Clarks Broyd Mid Chukka Boot(Men's) -Tan Leather
    Sale
    $119.00
    $140.00 15% off
    Timberland Earthkeepers Brook Park Chukka (Men's)
    New!
    Sale
    Timberland Earthkeepers Brook Park Chukka(Men's) -Red Brown Smooth
    Sale
    $79.95 - $129.95
    $130.00 up to 38% off
    Clarks Montacute Duke (Men's)
    New!
    Sale
    Clarks Montacute Duke(Men's) -Black Leather
    Sale
    $116.95 - $134.95
    $140.00 up to 16% off
    Clarks Stinson Lo (Men's)
    New!
    Sale
    Clarks Stinson Lo(Men's) -Beeswax Leather
    Sale
    Clarks Stinson Lo(Men's) -Black Leather
    Sale
    $89.95
    $100.00 10% off
    Clarks Folcroft Mid Chukka Boot (Men's)
    New!
    Sale
    Clarks Folcroft Mid Chukka Boot(Men's) -Black Leather
    Sale
    $82.95
    $120.00 31% off
    Rockport Rugged Bucks High Boot (Men's)
    New!
    Sale
    Rockport Rugged Bucks High Boot(Men's) -Dark Brown Leather
    Sale
    $77.95
    $130.00 40% off
    Clarks Kitna Mid Chukka Boot (Men's)
    New!
    Sale
    Clarks Kitna Mid Chukka Boot(Men's) -Mahogany Nubuck
    Sale
    $85.00
    $100.00 15% off
    New Balance 3020v1 Chukka Boot (Men's)
    New!
    Sale
    New Balance 3020v1 Chukka Boot(Men's) -Bitter Chocolate/Brindle
    Sale
    New Balance 3020v1 Chukka Boot(Men's) -Black/Black
    Sale
    $92.50
    $159.95 42% off