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    Discount Mens Casual Chukka Boots

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    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 Suede
    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) -Chestnut 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) -Gold Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Grey Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Greystone Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Khaki Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Navy Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Sage Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Wheat Suede
    Sale
    $74.99
    $100.00 25% 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
    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 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 Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Black/Black Leather
    Sale
    Clarks Desert Boot(Men's) -Burgundy Textile
    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
    $68.99 - $204.00
    $130.00 - $240.00 up to 51% off
    Clarks Wallabee (Men's)
    New!
    Sale
    Clarks Wallabee(Men's) -Burgundy Suede
    Sale
    Clarks Wallabee(Men's) -Dark Ochre Suede
    Sale
    Clarks Wallabee(Men's) -Red Suede
    Sale
    $116.99 - $134.95
    $135.00 - $160.00 up to 27% 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) -Chocolate Leather
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Dark Brown Leather
    Sale
    $98.45
    $110.00 - $140.00 up to 30% 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
    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
    Cole Haan Pinch Weekender Chukka (Men's)
    New!
    Sale
    Cole Haan Pinch Weekender Chukka(Men's) -Black Suede
    Sale
    Cole Haan Pinch Weekender Chukka(Men's) -Navy Ink Suede
    Sale
    Cole Haan Pinch Weekender Chukka(Men's) -Woodbury Suede
    Sale
    $98.95
    $150.00 34% 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 Navy 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
    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
    $139.95
    $250.00 44% off
    Sorel Paxson Chukka Waterproof Boot (Men's)
    New!
    Sale
    Sorel Paxson Chukka Waterproof Boot(Men's) -Black/Shark
    Sale
    Sorel Paxson Chukka Waterproof Boot(Men's) -Elk Full Grain/Black
    Sale
    $90.95
    $140.00 35% off
    ECCO Jeremy Hybrid Chukka Boot (Men's)
    New!
    Sale
    ECCO Jeremy Hybrid Chukka Boot(Men's) -Black Starbuck
    Sale
    ECCO Jeremy Hybrid Chukka Boot(Men's) -Cognac Cow Leather
    Sale
    $140.00 - $150.00
    $210.00 up to 33% 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
    Rockport Essential Details Waterproof Chukka Boot (Men's)
    New!
    Sale
    Rockport Essential Details Waterproof Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    Rockport Essential Details Waterproof Chukka Boot(Men's) -Dark Brown Full Grain Leather
    Sale
    $82.95 - $99.95
    $110.00 up to 25% 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
    Timberland Classic TBLŪ Chukka (Men's)
    New!
    Sale
    Timberland Classic TBLŪ Chukka(Men's) -Wheat Nubuck Leather
    Sale
    Timberland Classic TBLŪ Chukka(Men's) -Black Smooth Leather
    Sale
    $79.95 - $119.95
    $135.00 up to 41% 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
    $85.00
    $100.00 15% off
    Dr. Martens Lea 4-Eye Chukka Boot (Men's)
    New!
    Sale
    Dr. Martens Lea 4-Eye Chukka Boot(Men's) -Black Grizzly
    Sale
    Dr. Martens Lea 4-Eye Chukka Boot(Men's) -Dark Brown Grizzly
    Sale
    Dr. Martens Lea 4-Eye Chukka Boot(Men's) -Tan/Biscuit Grizzly
    Sale
    $89.95
    $115.00 22% off
    Drew Keith (Men's)
    New!
    Sale
    Drew Keith(Men's) -Black Leather
    Sale
    Drew Keith(Men's) -Brandy Leather
    Sale
    $166.45
    $190.00 12% off
    UGG Freamon Waterproof Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Waterproof Chukka Boot(Men's) -Brindle Full Grain Leather
    Sale
    $79.95 - $149.95
    $150.00 up to 47% off
    Rockport Classic Break Chukka Boot (Men's)
    New!
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Black Leather
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Black Suede
    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
    $97.95 - $106.45
    $120.00 - $135.00 up to 27% off
    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 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
    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
    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
    Lugz Mantle Mid Chukka Work Boot (Men's)
    New!
    Sale
    Lugz Mantle Mid Chukka Work Boot(Men's) -Black Synthetic
    Sale
    Lugz Mantle Mid Chukka Work Boot(Men's) -Golden Wheat/Tan-Khaki/Gum Synthetic
    Sale
    $44.99
    $54.99 18% off
    Clarks Chilver Hi Gore-Tex (Men's)
    New!
    Sale
    Clarks Chilver Hi Gore-Tex(Men's) -Black Leather
    Sale
    Clarks Chilver Hi Gore-Tex(Men's) -Dark Brown Nubuck
    Sale
    $120.99 - $121.95
    $160.00 up to 24% 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) -Brindle Suede
    Sale
    UGG Maksim Chukka Boot(Men's) -Stormy Seas Suede
    Sale
    $67.95 - $129.95
    $125.00 - $130.00 up to 46% off
    Cole Haan Original Grand Chukka (Men's)
    New!
    Sale
    Cole Haan Original Grand Chukka(Men's) -Black Rubber
    Sale
    Cole Haan Original Grand Chukka(Men's) -Black/Ironstone Leather
    Sale
    Cole Haan Original Grand Chukka(Men's) -Dark Roast/Cobblestone Leather
    Sale
    $139.95
    $180.00 22% off
    TOMS Chukka Boot Leather (Men's)
    New!
    Sale
    TOMS Chukka Boot Leather(Men's) -Black Pull Up Leather
    Sale
    $99.95
    $129.00 23% off
    ECCO Intrinsic Chukka Boot (Men's)
    New!
    Sale
    ECCO Intrinsic Chukka Boot(Men's) -Black Yak Leather
    Sale
    $120.00
    $170.00 29% 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
    Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
    New!
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(Men's) -Black Suede Suede
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(Men's) -Chestnut Suede
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(Men's) -Navy Suede
    Sale
    $86.45
    $100.00 14% off