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    Discount Mens Casual Chukka Boots

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    Steve Madden Harken Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Black  Leather
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Cognac Leather
    Sale
    $84.95 - $89.95
    $90.00 up to 6% 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 Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Brown Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Brown 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
    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
    $109.95
    $110.00 - $140.00 up to 21% off
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Green Leather
    Sale
    $69.95 - $239.95
    $130.00 - $240.00 up to 46% 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
    Rockport Rugged Bucks Waterproof Boot (Men's)
    New!
    Sale
    Rockport Rugged Bucks Waterproof Boot(Men's) -Castlerock Grey
    Sale
    $102.45 - $119.95
    $120.00 up to 15% 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) -Sand Suede
    Sale
    $94.95 - $109.95
    $100.00 - $110.00 up to 5% off
    Eastland Seneca (Men's)
    New!
    Sale
    Eastland Seneca(Men's) -Tan Waxee Leather
    Sale
    $99.95 - $109.95
    $110.00 up to 9% off
    Bed Stu Draco Chukka Boot (Men's)
    New!
    Sale
    Bed Stu Draco Chukka Boot(Men's) -Black Handwash Leather
    Sale
    Bed Stu Draco Chukka Boot(Men's) -Toast Zone Antiqued Leather
    Sale
    $139.95
    $175.00 20% off
    Timberland Earthkeepers Brook Park Chukka (Men's)
    New!
    Sale
    Timberland Earthkeepers Brook Park Chukka(Men's) -Red Brown Smooth
    Sale
    $104.95 - $129.95
    $130.00 up to 19% 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
    ECCO Turn GORE-TEX Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Boot(Men's) -Black Lexi Leather
    Sale
    $160.95 - $229.95
    $230.00 up to 30% off
    Cole Haan GrandPro Chukka Sneaker (Men's)
    New!
    Sale
    Cole Haan GrandPro Chukka Sneaker(Men's) -Black Oiled Velour Suede
    Sale
    $119.95 - $149.95
    $150.00 up to 20% off
    UGG Freamon Hyperweave Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Hyperweave Chukka Boot(Men's) -Black Textile
    Sale
    UGG Freamon Hyperweave Chukka Boot(Men's) -Burnt Olive Textile
    Sale
    UGG Freamon Hyperweave Chukka Boot(Men's) -Seal Textile
    Sale
    UGG Freamon Hyperweave Chukka Boot(Men's) -Tango Textile
    Sale
    $82.50 - $149.95
    $150.00 up to 45% 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) -Dark Bitter Chocolate Suede
    Sale
    Rockport Classic Break Chukka Boot(Men's) -Dark Brown Leather
    Sale
    $106.45 - $119.95
    $135.00 up to 21% off
    Rockport Ledge Hill Too Chukka Boot (Men's)
    New!
    Sale
    Rockport Ledge Hill Too Chukka Boot(Men's) -Black Leather
    Sale
    $109.95 - $149.95
    $150.00 up to 27% off
    Timberland Groveton Leather/Fabric Chukka (Men's)
    New!
    Sale
    Timberland Groveton Leather/Fabric Chukka(Men's) -Black Nubuck/Textile
    Sale
    Timberland Groveton Leather/Fabric Chukka(Men's) -Wheat Nubuck/Textile
    Sale
    $55.95 - $79.95
    $80.00 up to 30% 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
    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
    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
    $63.99
    $80.00 20% off
    Ariat Spitfire Chukka Boot (Men's)
    New!
    Sale
    Ariat Spitfire Chukka Boot(Men's) -Brown Bomber Full Grain Leather
    Sale
    Ariat Spitfire Chukka Boot(Men's) -Brown Bomber/Blue Laces Full Grain Leather
    Sale
    Ariat Spitfire Chukka Boot(Men's) -Vintage Bomber Full Grain Leather
    Sale
    $89.95
    $99.95 10% 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 Capra enerG Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Capra enerG Chukka Boot(Men's) -Pencil Lead Leather
    Sale
    $104.95 - $149.95
    $150.00 up to 30% off
    Rockport Total Motion Chukka Boot (Men's)
    New!
    Sale
    Rockport Total Motion Chukka Boot(Men's) -New Caramel Leather
    Sale
    $125.45
    $150.00 16% 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) -Brown 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
    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
    Stacy Adams Astro 53404 (Men's)
    New!
    Sale
    Stacy Adams Astro 53404(Men's) -Black Smooth Leather
    Sale
    $79.95 - $89.95
    $90.00 up to 11% off
    Timberland Carter Notch Plain Toe Waterproof Chukka Boot (Men's)
    New!
    Sale
    Timberland Carter Notch Plain Toe Waterproof Chukka Boot(Men's) -Black Riptide Galloper Full Grain Leather
    Sale
    $109.95 - $139.95
    $140.00 up to 21% off
    Frye Mark Chukka (Men's)
    New!
    Sale
    Frye Mark Chukka(Men's) -Dark Brown
    Sale
    $178.95
    $298.00 40% off
    Timberland Classic TBLŪ Chukka (Men's)
    New!
    Sale
    Timberland Classic TBLŪ Chukka(Men's) -Wheat Nubuck Leather
    Sale
    $109.95
    $135.00 19% off
    Rockport Rugged Bucks High Boot (Men's)
    New!
    Sale
    Rockport Rugged Bucks High Boot(Men's) -Black
    Sale
    Rockport Rugged Bucks High Boot(Men's) -Dark Brown Leather
    Sale
    $77.95 - $129.95
    $130.00 up to 40% off
    Florsheim Mogul Chukka Boot II (Men's)
    New!
    Sale
    Florsheim Mogul Chukka Boot II(Men's) -Black Smooth Leather
    Sale
    Florsheim Mogul Chukka Boot II(Men's) -Cognac Smooth Leather
    Sale
    Florsheim Mogul Chukka Boot II(Men's) -Snuff Suede
    Sale
    $89.95
    $120.00 25% off
    Clarks Holmby Top Chukka Boot (Men's)
    New!
    Sale
    Clarks Holmby Top Chukka Boot(Men's) -Brown Goat Full Grain Leather
    Sale
    $89.95 - $99.95
    $100.00 up to 10% off
    Deer Stags Seattle Boot (Men's)
    New!
    Sale
    Deer Stags Seattle Boot(Men's) -Black
    Sale
    Deer Stags Seattle Boot(Men's) -Luggage
    Sale
    $59.99
    $80.00 25% off
    Florsheim Castellano Chukka (Men's)
    New!
    Sale
    Florsheim Castellano Chukka(Men's) -Saddle Tan Leather
    Sale
    Florsheim Castellano Chukka(Men's) -Black Leather
    Sale
    Florsheim Castellano Chukka(Men's) -Brown Leather
    Sale
    $109.95
    $140.00 21% off