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

    Mens Casual Chukka Boots

    1-36 of 158 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) -Dark Brown Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Green Suede
    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) -Navy 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) -Dark Green Suede
    Clarks Desert Boot(Men's) -Mahogany Suede
    Clarks Desert Boot(Men's) -New Black Suede
    Clarks Desert Boot(Men's) -Oakwood Suede
    Clarks Desert Boot(Men's) -Taupe Canvas
    Clarks Desert Boot(Men's) -Taupe Distressed Suede
    $68.99 - $139.95
    $130.00 - $140.00 up to 51% off
    Clarks Stinson Hi Moc Toe Boot (Men's)
    New!
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Brown Leather
    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
    $82.99 - $99.95
    $100.00 - $110.00 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
    $134.95
    $135.00 - $160.00 up to 16% 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
    $125.99 - $126.99
    $140.00 up to 10% 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
    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
    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
    Naot Pilot (Men's)
    New!
    Sale
    Naot Pilot(Men's) -Brown Gradient Handcrafted Leather
    Naot Pilot(Men's) -Desert Suede
    Naot Pilot(Men's) -Gray Suede
    Naot Pilot(Men's) -Oily Coal Nubuck
    Naot Pilot(Men's) -Seal Brown Suede
    Naot Pilot(Men's) -Vintage Grey Leather
    $199.95 - $239.95
    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
    $98.45
    $110.00 10% 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
    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
    Dansko Jake Plain Toe Chukka Boot (Men's)
    New!
    Sale
    Dansko Jake Plain Toe Chukka Boot(Men's) -Black Antiqued Calf
    Sale
    Dansko Jake Plain Toe Chukka Boot(Men's) -Taupe Milled Nubuck
    Sale
    $129.95
    $194.95 33% off
    Cole Haan GrandPro Chukka Sneaker (Men's)
    New!
    Sale
    Cole Haan GrandPro Chukka Sneaker(Men's) -Black Oiled Velour Suede
    Sale
    Cole Haan GrandPro Chukka Sneaker(Men's) -Black Leather
    $97.50 - $149.95
    $150.00 up to 35% off
    Lugz Mantle Mid Chukka Work Boot (Men's)
    New!
    Sale
    Lugz Mantle Mid Chukka Work Boot(Men's) -Black Synthetic
    Sale
    Lugz Mantle Mid Chukka Work Boot(Men's) -Golden Wheat/Tan-Khaki/Gum Synthetic
    Sale
    $43.99
    $54.99 20% off