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    Mens Leather Chukka Boots

    1-36 of 142 results
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    Steve Madden Harken Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Black Leather
    New
    Steve Madden Harken Chukka Boot(Men's) -Grey Leather
    New
    Steve Madden Harken Chukka Boot(Men's) -Black  Leather
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Black Multi Leather/Fabric
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Brown Multi Leather/Fabric
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Cognac Leather
    Sale
    $71.95 - $89.95
    $90.00 up to 20% off
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Green Leather
    Sale
    Clarks Desert Boot(Men's) -Beeswax
    Clarks Desert Boot(Men's) -Brown
    Clarks Desert Boot(Men's) -Burgundy Textile
    Clarks Desert Boot(Men's) -Natural Tan
    Clarks Desert Boot(Men's) -Navy Tumbled Leather
    Clarks Desert Boot(Men's) -New Black Suede
    Clarks Desert Boot(Men's) -Oakwood Suede
    Clarks Desert Boot(Men's) -Taupe Distressed Suede
    $69.95 - $239.95
    $130.00 - $240.00 up to 46% off
    UGG Neumel Boot (Men's)
    New!
    Sale
    UGG Neumel Boot(Men's) -Chestnut
    UGG Neumel Boot(Men's) -China Tea
    UGG Neumel Boot(Men's) -New Navy Suede
    $129.95 - $139.95
    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
    Clarks Bushacre 2 Boot(Men's) -British Tan Leather
    Clarks Bushacre 2 Boot(Men's) -Khaki Leather
    Clarks Bushacre 2 Boot(Men's) -Light Grey Suede
    $59.99
    $100.00 40% off
    Clarks Melshire Top Chukka Boot (Men's)
    New!
    Sale
    Clarks Melshire Top Chukka Boot(Men's) -Black Cow Full Grain Leather
    Sale
    Clarks Melshire Top Chukka Boot(Men's) -Tan Cow Full Grain Leather
    Sale
    $69.95
    $110.00 36% off
    G.H. Bass & Co. Bennett Chukka (Men's)
    New!
    Sale
    G.H. Bass & Co. Bennett Chukka(Men's) -Black Tumbled Leather
    Sale
    G.H. Bass & Co. Bennett Chukka(Men's) -Brown Crazy Horse Leather
    Sale
    $99.99
    $135.00 26% 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
    Dr. Martens Lea 4-Eye Chukka Boot(Men's) -Black Grizzly
    Dr. Martens Lea 4-Eye Chukka Boot(Men's) -Dark Brown Grizzly
    $89.95 - $114.95
    $115.00 up to 22% off
    Boston Boot Co. Commonwealth Boot (Men's)
    New!
    Sale
    Boston Boot Co. Commonwealth Boot(Men's) -Black Leather
    Sale
    Boston Boot Co. Commonwealth Boot(Men's) -Brown/Nicotine Leather
    Sale
    Boston Boot Co. Commonwealth Boot(Men's) -Natural/White Leather
    Sale
    $99.95
    $207.00 52% 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 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
    Rockport Charson Lace Up Ankle Boot(Men's) -Chocolate Leather
    $89.95 - $139.95
    $140.00 up to 36% off
    UGG Maksim Chukka Boot (Men's)
    New!
    Sale
    UGG Maksim Chukka Boot(Men's) -New Navy Suede
    Sale
    UGG Maksim Chukka Boot(Men's) -Black Suede
    UGG Maksim Chukka Boot(Men's) -Brindle Suede
    UGG Maksim Chukka Boot(Men's) -Tamarind Suede
    $99.95 - $124.95
    $125.00 up to 20% 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
    Eastland Seneca (Men's)
    New!
    Sale
    Eastland Seneca(Men's) -Tan Waxee Leather
    Sale
    Eastland Seneca(Men's) -Bomber Brown Leather
    Eastland Seneca(Men's) -Brown Leather 2
    Eastland Seneca(Men's) -Gray Leather
    Eastland Seneca(Men's) -Khaki Suede
    Eastland Seneca(Men's) -Natural Leather
    Eastland Seneca(Men's) -Peanut Leather
    $99.95 - $109.95
    $110.00 up to 9% off
    UGG Freamon Capra enerG Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Capra enerG Chukka Boot(Men's) -Black Leather
    Sale
    UGG Freamon Capra enerG Chukka Boot(Men's) -Mole Leather
    Sale
    UGG Freamon Capra enerG Chukka Boot(Men's) -Pencil Lead Leather
    Sale
    $119.95
    $150.00 20% off
    ECCO Turn GORE-TEX Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Boot(Men's) -Black Lexi Leather
    Sale
    ECCO Turn GORE-TEX Boot(Men's) -Coffee Lexi Leather
    $204.95 - $229.95
    $230.00 up to 11% 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
    $119.95
    $140.00 14% off
    Twisted X Boots MDMS003 (Men's)
    New!
    Sale
    Twisted X Boots MDMS003(Men's) -Dusty Tan Leather
    Sale
    $69.95
    $104.99 33% off
    Steve Madden Hestonn (Men's)
    New!
    Sale
    Steve Madden Hestonn(Men's) -Tan Leather
    Sale
    $53.95
    $90.00 40% off
    Rockport Ledge Hill Too Chukka Boot (Men's)
    New!
    Sale
    Rockport Ledge Hill Too Chukka Boot(Men's) -Dark Bitter Chocolate Suede
    Sale
    Rockport Ledge Hill Too Chukka Boot(Men's) -Black Suede
    Rockport Ledge Hill Too Chukka Boot(Men's) -Dark Brown Leather
    $75.95 - $149.95
    $150.00 up to 49% 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
    UGG Brompton Tweed (Men's)
    New!
    Sale
    UGG Brompton Tweed(Men's) -Grizzly
    Sale
    $149.95
    $200.00 25% off
    Rockport Dressports Business Chukka Boot (Men's)
    New!
    Sale
    Rockport Dressports Business Chukka Boot(Men's) -Black Leather
    Sale
    $108.95
    $135.00 19% off