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    Leather Chukka Boots

    1-36 of 219 results
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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) -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) -Black Waxy Leather
    Clarks Bushacre 2 Boot(Men's) -Chestnut Suede
    Clarks Bushacre 2 Boot(Men's) -Dark Brown
    Clarks Bushacre 2 Boot(Men's) -Dark Tan Leather
    Clarks Bushacre 2 Boot(Men's) -Gold Suede
    Clarks Bushacre 2 Boot(Men's) -Khaki Leather
    Clarks Bushacre 2 Boot(Men's) -Tobacco Suede
    Clarks Bushacre 2 Boot(Men's) -Walnut Suede
    $59.99 - $99.95
    $100.00 up to 40% 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
    Timberland Killington Chukka Boot(Men's) -Black Full Grain Leather/Mesh
    Timberland Killington Chukka Boot(Men's) -Black Leather
    Timberland Killington Chukka Boot(Men's) -Medium Brown Full Grain Leather/Mesh
    $89.95 - $124.95
    $125.00 up to 28% off
    Steve Madden Harken Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Cognac Leather
    Sale
    Steve Madden Harken Chukka Boot(Men's) -Black  Leather
    Steve Madden Harken Chukka Boot(Men's) -Grey Leather
    $84.95 - $89.95
    $90.00 up to 6% off
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Beeswax
    Clarks Desert Boot(Men's) -Black Smooth
    Clarks Desert Boot(Men's) -Black/Black Leather
    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) -Olive Suede
    Clarks Desert Boot(Men's) -Tan Tumble
    Clarks Desert Boot(Men's) -Taupe Distressed Suede
    $129.95 - $239.95
    ECCO Jeremy Hybrid Chukka Boot (Men's)
    New!
    Sale
    ECCO Jeremy Hybrid Chukka Boot(Men's) -Black Cow Nubuck
    Sale
    ECCO Jeremy Hybrid Chukka Boot(Men's) -Cognac Cow Leather
    $157.50 - $209.95
    $210.00 up to 25% 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
    $109.95
    $110.00 - $140.00 up to 21% 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
    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 Wallabee Boot (Men's)
    New!
    Sale
    Clarks Wallabee Boot(Men's) -Beeswax/Beeswax Leather
    Clarks Wallabee Boot(Men's) -Black/Black Leather
    Clarks Wallabee Boot(Men's) -Black/Black Suede
    Clarks Wallabee Boot(Men's) -Dark Brown Suede
    Clarks Wallabee Boot(Men's) -Grey Suede
    Clarks Wallabee Boot(Men's) -Maple Suede
    Clarks Wallabee Boot(Men's) -Slate Blue Suede
    $139.95 - $159.95
    Naot Levanto Lace Up Ankle Boot (Women's)
    New!
    Sale
    Naot Levanto Lace Up Ankle Boot(Women's) -Gray Black Handcrafted Leather
    Sale
    Naot Levanto Lace Up Ankle Boot(Women's) -Midnight Suede
    Naot Levanto Lace Up Ankle Boot(Women's) -Seal Brown Suede
    Naot Levanto Lace Up Ankle Boot(Women's) -Vintage Grey Leather
    $132.00 - $219.95
    $220.00 up to 40% off
    Dr. Martens Cynthia Chukka Boot (Women's)
    New!
    Sale
    Dr. Martens Cynthia Chukka Boot(Women's) -Black New Oily Illusion Full Grain Leather
    Sale
    Dr. Martens Cynthia Chukka Boot(Women's) -Dark Brown New Oily Illusion Full Grain Leather
    Sale
    Dr. Martens Cynthia Chukka Boot(Women's) -Bone Temperley Analine Burnished Leather
    $99.95 - $119.95
    $120.00 up to 17% off
    Clarks Nevella Harper Chukka Boot (Women's)
    New!
    Sale
    Clarks Nevella Harper Chukka Boot(Women's) -Black Leather
    Sale
    $79.95
    $160.00 50% 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