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    Discount Mens 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
    UGG Freamon Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Chukka Boot(Men's) -Horchata Suede
    Sale
    $83.95 - $119.95
    $110.00 - $120.00 up to 30% 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 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
    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
    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
    Eastland Seneca (Men's)
    New!
    Sale
    Eastland Seneca(Men's) -Tan Waxee Leather
    Sale
    $99.95 - $109.95
    $110.00 up to 9% off
    Cole Haan Madison II Chukka Boot (Men's)
    New!
    Sale
    Cole Haan Madison II Chukka Boot(Men's) -Woodbury/Tortoise Leather
    Sale
    $170.00
    $270.00 37% 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
    Dr. Martens Ember Desert Boot (Men's)
    New!
    Sale
    Dr. Martens Ember Desert Boot(Men's) -Dark Brown Bronx Suede
    Sale
    $87.95 - $119.95
    $110.00 - $120.00 up to 20% 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
    $149.95
    $160.00 6% off
    Frye Sam Chukka (Men's)
    New!
    Sale
    Frye Sam Chukka(Men's) -Chestnut Antique Leather
    Sale
    Frye Sam Chukka(Men's) -Cognac Antique Leather
    Sale
    $223.95 - $234.95
    $298.00 up to 25% off
    Dr. Martens Sussex 3 Eye Chukka (Men's)
    New!
    Sale
    Dr. Martens Sussex 3 Eye Chukka(Men's) -Black Bear Track
    Sale
    Dr. Martens Sussex 3 Eye Chukka(Men's) -Dark Brown Bear Track
    Sale
    $84.98
    $95.00 11% off
    Timberland Earthkeepers Brook Park Chukka (Men's)
    New!
    Sale
    Timberland Earthkeepers Brook Park Chukka(Men's) -Brown Smooth
    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
    Dunham Gavin-DUN Chukka (Men's)
    New!
    Sale
    Dunham Gavin-DUN Chukka(Men's) -Black Leather
    Sale
    $108.50
    $160.00 32% 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
    Clarks Melshire Top Chukka Boot (Men's)
    New!
    Sale
    Clarks Melshire Top Chukka Boot(Men's) -Tan Cow Full Grain Leather
    Sale
    $69.95
    $110.00 36% off
    Lugz Freeman Chukka Boot (Men's)
    New!
    Sale
    Lugz Freeman Chukka Boot(Men's) -Seascape/Cream/Cymbal Textile
    Sale
    $59.95
    $79.99 25% 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
    Steve Madden Hestonn (Men's)
    New!
    Sale
    Steve Madden Hestonn(Men's) -Tan Leather
    Sale
    $53.95
    $90.00 40% 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
    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
    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
    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
    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
    Nunn Bush Galloway Plain Toe Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Galloway Plain Toe Chukka Boot(Men's) -Navy Suede
    Sale
    Nunn Bush Galloway Plain Toe Chukka Boot(Men's) -Tan Crazy Horse Leather
    Sale
    $63.99
    $80.00 20% 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
    Vans Premium Leather Desert Chukka Boot (Men's)
    New!
    Sale
    Vans Premium Leather Desert Chukka Boot(Men's) -Mojave Desert Suede
    Sale
    $76.95 - $104.95
    $90.00 - $105.00 up to 14% off