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    Mens Chukka Boots

    Men's chukka boots are made with the fashionable gentleman in mind. They are open-laced ankle boots with rubber or leather soles, and you can find great pairs at the best price right here. We have chukka boots for men from all the top brands, like Timberland, UGG, Dr. Martens, ECCO, Clarks and Johnston & Murphy, so you know you'll find the right pair.
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    UGG Freamon Capra enerG Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Capra enerG Chukka Boot(Men's) -Navy Goat Leather
    Sale
    UGG Freamon Capra enerG Chukka Boot(Men's) -Black Leather
    Sale
    UGG Freamon Capra enerG Chukka Boot(Men's) -Mole Leather
    Sale
    $80.95 - $94.95
    $150.00 up to 46% 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) -Marino Textile
    Sale
    $75.95 - $81.95
    $150.00 up to 49% off
    Merrell Downtown Chukka Boot (Men's)
    New!
    Sale
    Merrell Downtown Chukka Boot(Men's) -Brown Sugar Full Grain Leather
    Sale
    $89.95
    $120.00 25% 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) -Black Waxy Leather
    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) -Navy Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Wheat Suede
    Sale
    $49.97 - $99.95
    $100.00 up to 50% off
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Blue/Grey Suede
    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) -Brown
    Clarks Desert Boot(Men's) -New Black Suede
    Clarks Desert Boot(Men's) -Oakwood Suede
    Clarks Desert Boot(Men's) -Taupe Distressed Suede
    $97.45 - $129.95
    $130.00 - $140.00 up to 30% off
    Nunn Bush Galloway Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Galloway Chukka Boot(Men's) -Beige Suede
    Sale
    Nunn Bush Galloway Chukka Boot(Men's) -Dark Brown Suede
    Sale
    $55.95 - $56.00
    $80.00 up to 30% off
    Clarks Clarkdale Bara Chukka Boot (Men's)
    New!
    Sale
    Clarks Clarkdale Bara Chukka Boot(Men's) -Olive Suede
    Sale
    $144.99
    $170.00 15% off
    Ariat Spitfire Chukka Boot (Men's)
    New!
    Sale
    Ariat Spitfire Chukka Boot(Men's) -Aged Mahogany Leather
    New
    Ariat Spitfire Chukka Boot(Men's) -Brown Bomber Full Grain Leather
    Sale
    Ariat Spitfire Chukka Boot(Men's) -Brown Bomber 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
    $99.95 - $109.95 up to 18% 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
    $139.95
    $135.00 - $160.00 up to 13% off
    Caterpillar Mitch Chukka Boot (Men's)
    New!
    Sale
    Caterpillar Mitch Chukka Boot(Men's) -Dark Beige Leather
    Sale
    $66.95
    $90.00 26% off
    Dr. Martens Work Sussex 3 Eye Chukka (Men's)
    New!
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    Dr. Martens Work Sussex 3 Eye Chukka(Men's) -Black Bear Track
    Sale
    Dr. Martens Work Sussex 3 Eye Chukka(Men's) -Dark Brown Bear Track
    Sale
    $84.98
    $95.00 11% off
    Lugz Cargo Ankle Boot (Men's)
    New!
    Sale
    Lugz Cargo Ankle Boot(Men's) -Black Permahide
    Sale
    Lugz Cargo Ankle Boot(Men's) -Black/Charcoal Durabrush
    Sale
    Lugz Cargo Ankle Boot(Men's) -Golden Wheat/Cream/Bark/Gum Thermabuck
    Sale
    $43.99
    $69.99 37% off
    Florsheim Montinaro Chukka Boot (Men's)
    New!
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    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
    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
    $55.95
    $80.00 30% 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
    $111.45
    $140.00 20% off
    Nunn Bush Littleton Plain Toe Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Littleton Plain Toe Chukka Boot(Men's) -Brown Leather
    Sale
    Nunn Bush Littleton Plain Toe Chukka Boot(Men's) -Tan Leather
    Sale
    $71.95
    $90.00 20% 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
    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
    Dr. Martens Bonny 6 Eye Chukka Boot
    New!
    Sale
    Dr. Martens Bonny 6 Eye Chukka Boot -Black 8 Oz Canvas
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    Dr. Martens Bonny 6 Eye Chukka Boot -Indigo 8 Oz Canvas
    Sale
    Dr. Martens Bonny 6 Eye Chukka Boot -Mid Grey 8 Oz Canvas
    Sale
    Dr. Martens Bonny 6 Eye Chukka Boot -Navy Extra Tough Nylon/Rubbery
    Sale
    Dr. Martens Bonny 6 Eye Chukka Boot -Port Royale Canvas
    Sale
    $42.97 - $67.99
    $80.00 - $85.00 up to 49% off