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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.
    1-36 of 250 results
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    Dockers Longden Chukka Boot (Men's)
    Dockers Longden Chukka Boot (Men's)
    Dockers Longden Chukka Boot (Men's)
    Dockers Longden Chukka Boot (Men's)
    New!
    Sale
    Dockers Longden Chukka Boot(Men's)-Taupe Suede
    Sale
    Dockers Longden Chukka Boot(Men's)-Black Burnished Full Grain Leather
    Sale
    Dockers Longden Chukka Boot(Men's)-Red Brown Burnished Full Grain Leather
    Sale
    $79.99
    $110.00 27% off
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's)-Black Smooth
    Clarks Desert Boot(Men's)-Green Leather
    Sale
    Clarks Desert Boot(Men's)-Beeswax
    Clarks Desert Boot(Men's)-Brown
    Clarks Desert Boot(Men's)-Khaki Leather
    Clarks Desert Boot(Men's)-New Black Suede
    Clarks Desert Boot(Men's)-Oakwood Suede
    Clarks Desert Boot(Men's)-Off White Interest Suede
    Clarks Desert Boot(Men's)-Taupe Distressed Suede
    $59.99 - $159.95
    $130.00 - $160.00 up to 54% off
    Clarks Bushacre 2 Boot (Men's)
    Clarks Bushacre 2 Boot (Men's)
    Clarks Bushacre 2 Boot (Men's)
    Clarks Bushacre 2 Boot (Men's)
    Clarks Bushacre 2 Boot (Men's)
    Clarks Bushacre 2 Boot (Men's)
    New!
    Sale
    Clarks Bushacre 2 Boot(Men's)-Beeswax 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
    $84.95
    $100.00 15% off
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Harken Chukka Boot(Men's)-Black  Leather
    Steve Madden Harken Chukka Boot(Men's)-Black Multi Leather/Fabric
    Steve Madden Harken Chukka Boot(Men's)-Brown Multi Leather/Fabric
    Steve Madden Harken Chukka Boot(Men's)-Cognac Leather
    $89.95
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    New!
    Sale
    Johnston & Murphy Copeland Chukka Boot(Men's)-Black Tumbled Full Grain Leather
    Johnston & Murphy Copeland Chukka Boot(Men's)-Camel Suede
    Johnston & Murphy Copeland Chukka Boot(Men's)-Dark Gray Suede
    Johnston & Murphy Copeland Chukka Boot(Men's)-Navy Suede
    Johnston & Murphy Copeland Chukka Boot(Men's)-Red Brown Oiled Full Grain Leather
    Johnston & Murphy Copeland Chukka Boot(Men's)-Tan Oiled Full Grain
    Johnston & Murphy Copeland Chukka Boot(Men's)-Taupe Water-Resistant Suede
    $149.95 - $154.95
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    New!
    Sale
    Clarks Wallabee Boot(Men's)-Dark Green Suede
    Sale
    Clarks Wallabee Boot(Men's)-Beeswax/Beeswax Leather
    Clarks Wallabee Boot(Men's)-Dark Brown Suede
    Clarks Wallabee Boot(Men's)-Maple Suede
    $99.99 - $139.95
    $140.00 up to 29% off
    Clarks Stratton Limit Boot (Men's)
    Clarks Stratton Limit Boot (Men's)
    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
    Rockport Charson Lace Up Ankle Boot (Men's)
    Rockport Charson Lace Up Ankle Boot (Men's)
    Rockport Charson Lace Up Ankle Boot (Men's)
    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
    $99.95 - $139.95
    $130.00 - $140.00 up to 23% off
    UGG Freamon Chukka Boot (Men's)
    UGG Freamon Chukka Boot (Men's)
    UGG Freamon Chukka Boot (Men's)
    UGG Freamon Chukka Boot (Men's)
    New!
    Sale
    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
    Nunn Bush Rawson Chukka (Men's)
    Nunn Bush Rawson Chukka (Men's)
    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
    Clarks Bushacre 2 (Men's)
    Clarks Bushacre 2 (Men's)
    Clarks Bushacre 2 (Men's)
    Clarks Bushacre 2 (Men's)
    Clarks Bushacre 2 (Men's)
    New!
    Sale
    Clarks Bushacre 2(Men's) -Black Leather
    Sale
    Clarks Bushacre 2(Men's) -Dark Green Suede
    Sale
    Clarks Bushacre 2(Men's) -Navy Leather
    Sale
    Clarks Bushacre 2(Men's) -Navy Suede
    Sale
    $64.99 - $89.95
    $100.00 up to 35% off
    Nunn Bush Woodbury (Men's)
    Nunn Bush Woodbury (Men's)
    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
    Timberland Classic TBLŪ Chukka (Men's)
    Timberland Classic TBLŪ Chukka (Men's)
    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
    Dr. Martens Sussex 3 Eye Chukka (Men's)
    Dr. Martens Sussex 3 Eye Chukka (Men's)
    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
    UGG Bosley Chukka Boot (Men's)
    UGG Bosley Chukka Boot (Men's)
    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
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    New!
    Sale
    Clarks Stinson Hi Moc Toe Boot(Men's) -Grey Leather
    New
    Clarks Stinson Hi Moc Toe Boot(Men's) -Loden Green
    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) -Wheat 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
    $69.99 - $109.95
    $100.00 - $110.00 up to 30% off
    G.H. Bass & Co. Bennett Chukka (Men's)
    G.H. Bass & Co. Bennett Chukka (Men's)
    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
    $94.95
    $135.00 30% off
    Rockport Essential Details Waterproof Chukka Boot (Men's)
    Rockport Essential Details Waterproof Chukka Boot (Men's)
    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
    $99.95 - $109.95
    $110.00 up to 9% off
    Rockport Rugged Bucks Waterproof Boot (Men's)
    Rockport Rugged Bucks Waterproof Boot (Men's)
    Rockport Rugged Bucks Waterproof Boot (Men's)
    Rockport Rugged Bucks Waterproof Boot (Men's)
    New!
    Sale
    Rockport Rugged Bucks Waterproof Boot(Men's) -Boston Tan
    Rockport Rugged Bucks Waterproof Boot(Men's) -Castlerock Grey
    Rockport Rugged Bucks Waterproof Boot(Men's) -Tan Full Grain Leather
    $109.95 - $119.95
    ECCO Turn GORE-TEX Boot (Men's)
    ECCO Turn GORE-TEX Boot (Men's)
    ECCO Turn GORE-TEX Boot (Men's)
    ECCO Turn GORE-TEX Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Boot(Men's) -Mocha Oil Nubuck
    Sale
    ECCO Turn GORE-TEX Boot(Men's) -Black Lexi Leather
    ECCO Turn GORE-TEX Boot(Men's) -Coffee Lexi Leather
    $172.95 - $229.95
    $230.00 up to 25% off
    Born Jax (Men's)
    Born Jax (Men's)
    New!
    Sale
    Born Jax(Men's) -Brown Full Grain Leather
    Sale
    $98.95
    $110.00 10% off
    Woolrich Lane (Men's)
    Woolrich Lane (Men's)
    Woolrich Lane (Men's)
    Woolrich Lane (Men's)
    New!
    Sale
    Woolrich Lane(Men's) -Ballentyne
    Sale
    Woolrich Lane(Men's) -Camel
    Sale
    Woolrich Lane(Men's) -Yellowstone
    Sale
    $70.95
    $160.00 56% off
    Florsheim Indie Cap Boot (Men's)
    Florsheim Indie Cap Boot (Men's)
    Florsheim Indie Cap Boot (Men's)
    Florsheim Indie Cap Boot (Men's)
    New!
    Sale
    Florsheim Indie Cap Boot(Men's) -Black Milled Leather
    Florsheim Indie Cap Boot(Men's) -Chestnut Smooth Leather
    Florsheim Indie Cap Boot(Men's) -Saddle Tan Leather
    $174.95
    Timberland Premium Chukka (Men's)
    Timberland Premium Chukka (Men's)
    New!
    Sale
    Timberland Premium Chukka(Men's) -Wheat Nubuck
    Sale
    $134.95
    $145.00 7% off
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    New!
    Sale
    Clarks Wallabee(Men's) -Navy
    New
    Clarks Wallabee(Men's) -Beeswax/Beeswax Leather
    Clarks Wallabee(Men's) -Black/Black Leather
    Clarks Wallabee(Men's) -Maple Suede
    $134.95 - $149.95
    UGG Brompton Tweed (Men's)
    UGG Brompton Tweed (Men's)
    New!
    Sale
    UGG Brompton Tweed(Men's) -Grizzly
    Sale
    $149.95
    $200.00 25% off
    Pikolinos Glasgow 05M-6030F (Men's)
    Pikolinos Glasgow 05M-6030F (Men's)
    Pikolinos Glasgow 05M-6030F (Men's)
    New!
    Sale
    Pikolinos Glasgow 05M-6030F(Men's) -Choco/Cuero Leather
    Pikolinos Glasgow 05M-6030F(Men's) -Cuero
    $195.00 - $199.95
    Nunn Bush Robinson Chukka Boot (Men's)
    Nunn Bush Robinson Chukka Boot (Men's)
    Nunn Bush Robinson Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Robinson Chukka Boot(Men's) -Black Leather
    Sale
    Nunn Bush Robinson Chukka Boot(Men's) -Chestnut Leather
    Sale
    $72.00
    $90.00 20% off
    Florsheim Heritage Wingtip Boot (Men's)
    Florsheim Heritage Wingtip Boot (Men's)
    Florsheim Heritage Wingtip Boot (Men's)
    Florsheim Heritage Wingtip Boot (Men's)
    New!
    Sale
    Florsheim Heritage Wingtip Boot(Men's) -Black Smooth/Milled
    Florsheim Heritage Wingtip Boot(Men's) -Cognac Smooth/Milled
    Florsheim Heritage Wingtip Boot(Men's) -Cognac Smooth/Navy
    $189.95
    UGG Freamon Capra Chukka Boot (Men's)
    UGG Freamon Capra Chukka Boot (Men's)
    UGG Freamon Capra Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Capra Chukka Boot(Men's) -Chocolate
    Sale
    UGG Freamon Capra Chukka Boot(Men's) -Primer Leather
    Sale
    $97.95
    $130.00 25% off
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    Put the final stylish touch on your look with the refreshing Vershire Chukka Boot. Showing off a handsewn genuine moccasin ...
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