Phone
    Call
    1 (888) 200 - 8414
    Mon - Fri: 8:00 AM - Midnight ET
    Sat - Sun: 8:00 AM - 11:00 PM ET

    Casual Chukka Boots

    1-36 of 176 results
     1 2 3 4 5 
    Sort by
    Display
    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) -Dark Brown Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Tan Leather
    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) -Wheat Suede
    Sale
    $64.99 - $89.99
    $100.00 up to 35% off
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Black/Black Leather
    Sale
    Clarks Desert Boot(Men's) -Mahogany Suede
    Sale
    Clarks Desert Boot(Men's) -Navy Canvas
    Sale
    Clarks Desert Boot(Men's) -Taupe Canvas
    Sale
    Clarks Desert Boot(Men's) -Beeswax
    Clarks Desert Boot(Men's) -Blue/Grey Suede
    Clarks Desert Boot(Men's) -Brown
    Clarks Desert Boot(Men's) -New Black Suede
    Clarks Desert Boot(Men's) -Oakwood Suede
    Clarks Desert Boot(Men's) -Taupe Distressed
    Clarks Desert Boot(Men's) -Taupe Distressed Suede
    $68.99 - $139.95
    $130.00 - $140.00 up to 51% off
    Clarks Wallabee Boot (Men's)
    New!
    Sale
    Clarks Wallabee Boot(Men's) -Black/Black Leather
    Sale
    Clarks Wallabee Boot(Men's) -Beeswax/Beeswax Leather
    Clarks Wallabee Boot(Men's) -Black/Black Suede
    Clarks Wallabee Boot(Men's) -Dark Brown Suede
    Clarks Wallabee Boot(Men's) -Maple Suede
    $104.99 - $140.00
    $140.00 up to 25% off
    Clarks Wallabee (Men's)
    New!
    Sale
    Clarks Wallabee(Men's) -Beeswax/Beeswax Leather
    Sale
    Clarks Wallabee(Men's) -Black/Black Leather
    Sale
    Clarks Wallabee(Men's) -Maple Suede
    $135.00
    $135.00 - $160.00 up to 16% 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
    $55.95
    $80.00 30% off
    Clarks Medora Sage Chukka Boot (Women's)
    New!
    Sale
    Clarks Medora Sage Chukka Boot(Women's) -Black Suede/Full Grain Leather
    Sale
    Clarks Medora Sage Chukka Boot(Women's) -Burgundy Suede/Full Grain Leather
    Sale
    Clarks Medora Sage Chukka Boot(Women's) -Olive Suede/Full Grain Leather
    Sale
    $71.99
    $120.00 40% 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
    $128.99
    $140.00 8% off
    Clarks Stinson Hi Moc Toe Boot (Men's)
    New!
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Tan Leather
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Beeswax Leather
    Clarks Stinson Hi Moc Toe Boot(Men's) -Black Oily Leather
    Clarks Stinson Hi Moc Toe Boot(Men's) -Brown Oily Leather
    Clarks Stinson Hi Moc Toe Boot(Men's) -Sand Suede
    $76.99 - $99.95
    $100.00 - $110.00 up to 30% off
    Florsheim Montinaro Chukka Boot (Men's)
    New!
    Sale
    Florsheim Montinaro Chukka Boot(Men's) -Saddle Tan Smooth Leather
    Sale
    Florsheim Montinaro Chukka Boot(Men's) -Black Smooth Leather
    Sale
    $99.95
    $109.95 9% off
    UGG Freamon Waterproof Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Waterproof Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    UGG Freamon Waterproof Chukka Boot(Men's) -Grizzly Full Grain Leather
    Sale
    $112.95
    $150.00 25% 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
    G.H. Bass & Co. Bennett Chukka(Men's) -Tan Soft Tumbled Full Grain Leather
    $89.99 - $99.99
    $110.00 - $135.00 up to 26% 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 Leather
    Timberland Killington Chukka Boot(Men's) -Light Brown Full Grain Leather
    Timberland Killington Chukka Boot(Men's) -Medium Brown Full Grain Leather/Mesh
    $74.95 - $124.95
    $125.00 up to 40% off
    Clarks Desert Boot (Women's)
    New!
    Sale
    Clarks Desert Boot(Women's) -Dark Navy Suede
    Sale
    Clarks Desert Boot(Women's) -Taupe Distressed
    Sale
    Clarks Desert Boot(Women's) -Beeswax Leather
    Clarks Desert Boot(Women's) -Black Suede
    Clarks Desert Boot(Women's) -Oakwood Suede
    $109.99 - $140.00
    $120.00 - $140.00 up to 14% off
    Wolverine Bedford Soft Toe Chukka Boot (Men's)
    New!
    Sale
    Wolverine Bedford Soft Toe Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    Wolverine Bedford Soft Toe Chukka Boot(Men's) -Brown Full Grain Leather
    Sale
    $88.99
    $115.00 23% off
    Clarks Stratton Limit Boot (Men's)
    New!
    Sale
    Clarks Stratton Limit Boot(Men's) -Brown Leather
    Sale
    Clarks Stratton Limit Boot(Men's) -Black Leather
    $101.25 - $134.95
    $135.00 up to 25% off
    Dansko Joy Chukka Boot (Women's)
    New!
    Sale
    Dansko Joy Chukka Boot(Women's) -Walnut Nubuck
    Sale
    Dansko Joy Chukka Boot(Women's) -Black Nubuck
    Dansko Joy Chukka Boot(Women's) -Navy Nubuck
    $103.95 - $164.95
    $165.00 up to 37% 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
    Clarks Desert Trek (Men's)
    New!
    Sale
    Clarks Desert Trek(Men's) -Black Suede
    Clarks Desert Trek(Men's) -Chestnut Leather
    $139.95 - $140.00