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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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    ECCO Turn GORE-TEX Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Boot(Men's) -Coffee Lexi Leather
    ECCO Turn GORE-TEX Boot(Men's) -Black Lexi Leather
    Sale
    $172.95 - $229.95
    $230.00 up to 25% off
    Cole Haan Cranston Chukka Boot (Men's)
    New!
    Sale
    Cole Haan Cranston Chukka Boot(Men's) -Chestnut Tumble Leather
    Cole Haan Cranston Chukka Boot(Men's) -Castlerock Tumble Leather
    Sale
    $139.99
    $280.00 50% off
    UGG Freamon Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Chukka Boot(Men's) -Horchata Suede
    New
    UGG Freamon Chukka Boot(Men's) -Black Suede
    UGG Freamon Chukka Boot(Men's) -Chestnut/White
    UGG Freamon Chukka Boot(Men's) -New Navy Suede
    $109.95 - $119.95
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Oakwood Suede
    Clarks Desert Boot(Men's) -Burgundy Textile
    New
    Clarks Desert Boot(Men's) -Fudge Suede
    New
    Clarks Desert Boot(Men's) -Green Leather
    Sale
    Clarks Desert Boot(Men's) -Beeswax
    Clarks Desert Boot(Men's) -Black Smooth
    Clarks Desert Boot(Men's) -Brown
    Clarks Desert Boot(Men's) -Khaki Leather
    Clarks Desert Boot(Men's) -Natural Tan
    New
    Clarks Desert Boot(Men's) -Navy Tumbled Leather
    New
    Clarks Desert Boot(Men's) -New Black Suede
    Clarks Desert Boot(Men's) -Tan Tumble
    New
    Clarks Desert Boot(Men's) -Taupe Distressed Suede
    $59.99 - $239.95
    $130.00 - $240.00 up to 54% 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) -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
    $84.95 - $99.95
    $100.00 up to 15% 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
    Clarks Stinson Hi Moc Toe Boot (Men's)
    New!
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -British Tan Leather
    New
    Clarks Stinson Hi Moc Toe Boot(Men's) -Grey Leather
    New
    Clarks Stinson Hi Moc Toe Boot(Men's) -Black Suede
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Sand Suede
    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) -Khaki Leather
    New
    Clarks Stinson Hi Moc Toe Boot(Men's) -Loden Green
    New
    $94.95 - $109.95
    $100.00 - $110.00 up to 5% 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
    Timberland Classic TBLŪ Chukka (Men's)
    New!
    Sale
    Timberland Classic TBLŪ Chukka(Men's) -Wheat Nubuck Leather
    Sale
    Timberland Classic TBLŪ Chukka(Men's) -Black Smooth Leather
    Sale
    $109.95 - $119.95
    $135.00 up to 19% off
    UGG Maksim Chukka Boot (Men's)
    New!
    Sale
    UGG Maksim Chukka Boot(Men's) -Black Suede
    New
    UGG Maksim Chukka Boot(Men's) -Brindle Suede
    New
    UGG Maksim Chukka Boot(Men's) -New Navy Suede
    New
    UGG Maksim Chukka Boot(Men's) -Tamarind Suede
    New
    $124.95
    Dr. Martens Sussex 3 Eye Chukka (Men's)
    New!
    Sale
    Dr. Martens Sussex 3 Eye Chukka(Men's) -Black Bear Track
    Sale
    Dr. Martens Sussex 3 Eye Chukka(Men's) -Dark Brown Bear Track
    Sale
    $84.98
    $95.00 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) -Chocolate Leather
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Dark Brown Leather
    Sale
    $87.95
    $140.00 37% off
    Clarks Wallabee (Men's)
    New!
    Sale
    Clarks Wallabee(Men's) -Charcoal Leather
    New
    Clarks Wallabee(Men's) -Fudge Suede
    New
    Clarks Wallabee(Men's) -Beeswax/Beeswax Leather
    Clarks Wallabee(Men's) -Black/Black Leather
    Clarks Wallabee(Men's) -Maple Suede
    Clarks Wallabee(Men's) -Natural Tan
    New
    Clarks Wallabee(Men's) -Navy Tumbled Leather
    New
    Clarks Wallabee(Men's) -Ochre Suede
    New
    Clarks Wallabee(Men's) -Tan Tumble
    New
    Clarks Wallabee(Men's) -Taupe Synthetic
    New
    $134.95 - $239.95
    Timberland Premium Chukka (Men's)
    New!
    Sale
    Timberland Premium Chukka(Men's) -Wheat Nubuck
    Sale
    $134.95
    $145.00 7% off
    UGG Bosley Chukka Boot (Men's)
    New!
    Sale
    UGG Bosley Chukka Boot(Men's) -Black
    Sale
    UGG Bosley Chukka Boot(Men's) -Chestnut
    Sale
    $142.95
    $190.00 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
    $99.99
    $135.00 26% off
    Frye Mark Chukka (Men's)
    New!
    Sale
    Frye Mark Chukka(Men's) -Copper
    Sale
    Frye Mark Chukka(Men's) -Dark Brown
    Sale
    $223.95
    $298.00 25% off
    Rockport Essential Details Waterproof Chukka Boot (Men's)
    New!
    Sale
    Rockport Essential Details Waterproof Chukka Boot(Men's) -Black Full Grain Leather
    Sale
    Rockport Essential Details Waterproof Chukka Boot(Men's) -Dark Brown Full Grain Leather
    Sale
    $91.95 - $99.95
    $110.00 up to 16% off
    Drew Keith (Men's)
    New!
    Sale
    Drew Keith(Men's) -Black Leather
    Sale
    Drew Keith(Men's) -Brandy Leather
    Sale
    $166.45
    $190.00 12% off
    Nunn Bush Hawley Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Hawley Chukka Boot(Men's) -Black Leather
    Sale
    Nunn Bush Hawley Chukka Boot(Men's) -Brown Leather
    Sale
    $72.00
    $90.00 20% off
    Nunn Bush Woodbury (Men's)
    New!
    Sale
    Nunn Bush Woodbury(Men's) -Brown Suede
    Sale
    Nunn Bush Woodbury(Men's) -Sand Suede
    Sale
    $64.00
    $80.00 20% off
    Nunn Bush Rawson Chukka (Men's)
    New!
    Sale
    Nunn Bush Rawson Chukka(Men's) -Black Leather
    Sale
    Nunn Bush Rawson Chukka(Men's) -Chestnut Leather
    Sale
    $71.95
    $90.00 20% 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
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    Stacy Adams Madison II Plain Toe Chukka Boot
    Description:
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    Put the final stylish touch on your look with the refreshing Vershire Chukka Boot. Showing off a handsewn genuine moccasin ...
    Sebago Vershire Chukka Boot (Men's)
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    Enhance your casual style wearing the classic Sperry A/O Mini Lug Chukka Boot. It features a non-slip rubber outsole with ...
    Sperry Top-Sider A/O Mini Lug Chukka Boot (Men's)
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