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    Mens Chelsea Boots

    Looking for a pair of men's Chelsea boots for the fall and winter seasons? With all colors and sizes and variety of styles and features, we have the best collection of fashionable Chelsea boots for men. Choose from brands like Dr. Martens, Keen, Timberland and Born. With our top brands and low prices, you're sure to find the ideal pair of men's Chelsea boots.
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    Blundstone Original 500 Series Boot
    New!
    Sale
    Blundstone Original 500 Series Boot -Brown/Multi
    Sale
    Blundstone Original 500 Series Boot -Black
    Sale
    Blundstone Original 500 Series Boot -Stout Brown
    Sale
    Blundstone Original 500 Series Boot -Stout Brown/Blue Gore Leather
    Sale
    Blundstone Original 500 Series Boot -Stout Brown/Burnt Orange
    Sale
    Blundstone Original 500 Series Boot -Stout Brown/Olive Gore
    Sale
    $130.95
    $174.95 25% off
    Timberland Carter Notch Plain Toe Chelsea Boot (Men's)
    New!
    Sale
    Timberland Carter Notch Plain Toe Chelsea Boot(Men's) -Dark Brown Full Grain Leather
    Sale
    Timberland Carter Notch Plain Toe Chelsea Boot(Men's) -Black Riptide Galloper Full Grain Leather
    Sale
    Timberland Carter Notch Plain Toe Chelsea Boot(Men's) -Turkish Coffee Poseidon Full Grain Leather
    Sale
    $112.95
    $150.00 25% off
    Cole Haan Grantland Waterproof Chelsea Boot (Men's)
    New!
    Sale
    Cole Haan Grantland Waterproof Chelsea Boot(Men's) -Woodbury Waterproof Leather
    Sale
    Cole Haan Grantland Waterproof Chelsea Boot(Men's) -Black Waterproof Leather
    Sale
    Cole Haan Grantland Waterproof Chelsea Boot(Men's) -Burnt Chili Waterproof Leather
    Sale
    $180.95
    $240.00 25% off
    Sperry Top-Sider Gold Crepe Chelsea Boot (Men's)
    New!
    Sale
    Sperry Top-Sider Gold Crepe Chelsea Boot(Men's) -Black Full Grain Leather
    Sale
    Sperry Top-Sider Gold Crepe Chelsea Boot(Men's) -Dark Snuff Suede
    Sale
    Sperry Top-Sider Gold Crepe Chelsea Boot(Men's) -Sand Suede
    Sale
    $153.95
    $219.95 30% off
    Blundstone Super 550 Series Boot
    New!
    Sale
    Blundstone Super 550 Series Boot -Black
    Sale
    Blundstone Super 550 Series Boot -Black/Red Gore/Red Sole
    Sale
    Blundstone Super 550 Series Boot -Brown Crazy Horse
    Sale
    Blundstone Super 550 Series Boot -Burgundy
    Sale
    Blundstone Super 550 Series Boot -Grizzly Brown Leather
    Sale
    Blundstone Super 550 Series Boot -Rustic Black
    Sale
    Blundstone Super 550 Series Boot -Rustic Black Brogue Leather
    Sale
    Blundstone Super 550 Series Boot -Rustic Brown Brogue Leather
    Sale
    Blundstone Super 550 Series Boot -Steel Grey Leather
    Sale
    Blundstone Super 550 Series Boot -Steel Grey/Black Gore
    Sale
    Blundstone Super 550 Series Boot -Stout Brown/Olive
    Sale
    Blundstone Super 550 Series Boot -Walnut
    Sale
    Blundstone Super 550 Series Boot -Rustic Brown
    $135.95 - $194.95
    $194.95 up to 30% off
    Dr. Martens 2976 Chelsea Boot
    New!
    Sale
    Dr. Martens 2976 Chelsea Boot -Black Smooth
    Sale
    Dr. Martens 2976 Chelsea Boot -Charro/Dark Brown Brando/Hi Suede Waterproof
    Sale
    Dr. Martens 2976 Chelsea Boot -Cherry Red Antique Temperley
    Sale
    Dr. Martens 2976 Chelsea Boot -Cherry Red Smooth
    Sale
    Dr. Martens 2976 Chelsea Boot -Navy Antique Temperley
    Sale
    Dr. Martens 2976 Chelsea Boot -Black Carpathian
    Dr. Martens 2976 Chelsea Boot -Black Felix Rub Off Vegan
    Dr. Martens 2976 Chelsea Boot -Black Inuck
    Dr. Martens 2976 Chelsea Boot -Black Smooth Leather
    Dr. Martens 2976 Chelsea Boot -Cherry Red Bush
    Dr. Martens 2976 Chelsea Boot -Cherry Red Smooth Leather
    Dr. Martens 2976 Chelsea Boot -Gaucho Crazy Horse
    $105.00 - $144.95
    $145.00 up to 28% off
    Dr. Martens 101 6-Eye Boot
    New!
    Sale
    Dr. Martens 101 6-Eye Boot -Black Brando Full Grain Waxy Leather
    Dr. Martens 101 6-Eye Boot -Black Smooth
    Dr. Martens 101 6-Eye Boot -Black Vintage Smooth Leather
    Dr. Martens 101 6-Eye Boot -Cherry Red Smooth
    Dr. Martens 101 6-Eye Boot -Oxblood Brando Full Grain Waxy Leather
    Dr. Martens 101 6-Eye Boot -Oxblood Vintage Smooth Leather
    Dr. Martens 101 6-Eye Boot -Smokethorn Brando Full Grain Waxy Leather
    Dr. Martens 101 6-Eye Boot -White Smooth Leather
    $129.95 - $134.95
    Blundstone Dress Series Boot
    New!
    Sale
    Blundstone Dress Series Boot -Black
    Sale
    Blundstone Dress Series Boot -Brown
    Sale
    Blundstone Dress Series Boot -Brown Crazy Horse
    Sale
    Blundstone Dress Series Boot -Burgundy
    Sale
    Blundstone Dress Series Boot -Grizzly Brown Leather
    Sale
    Blundstone Dress Series Boot -Rustic Black
    Sale
    Blundstone Dress Series Boot -Rustic Brown
    Sale
    $125.95 - $134.95
    $179.95 up to 30% off
    Arche Zorak Nubuck Leather Chelsea Bootie (Men's)
    New!
    Sale
    Arche Zorak Nubuck Leather Chelsea Bootie(Men's) -Arock Nubuck
    Sale
    Arche Zorak Nubuck Leather Chelsea Bootie(Men's) -Noir Nubuck
    Sale
    $357.00
    $595.00 40% off
    Blundstone Thermal Series Boot
    New!
    Sale
    Blundstone Thermal Series Boot -Black Leather
    Sale
    Blundstone Thermal Series Boot -Rustic Brown
    Sale
    $156.95
    $209.95 25% off
    Blundstone #490 Soft Toe Chelsea Boot (Men's)
    New!
    Sale
    Blundstone #490 Soft Toe Chelsea Boot(Men's) -Stout Brown Leather
    Sale
    $115.95
    $154.95 25% off
    Clarks Clarkdale Gobi Chelsea Boot (Men's)
    New!
    Sale
    Clarks Clarkdale Gobi Chelsea Boot(Men's) -Black Suede
    Sale
    Clarks Clarkdale Gobi Chelsea Boot(Men's) -Dark Brown Suede
    Clarks Clarkdale Gobi Chelsea Boot(Men's) -Olive Suede
    $144.50 - $169.95
    $170.00 up to 15% off
    Rockport Wynstin Chelsea Boot (Men's)
    New!
    Sale
    Rockport Wynstin Chelsea Boot(Men's) -Black Leather
    Sale
    Rockport Wynstin Chelsea Boot(Men's) -Dark Bitter Chocolate Leather
    Sale
    Rockport Wynstin Chelsea Boot(Men's) -Tobacco Leather
    Sale
    $92.95
    $130.00 28% off
    Nunn Bush Hartley Chelsea Boot (Men's)
    New!
    Sale
    Nunn Bush Hartley Chelsea Boot(Men's) -Black Leather
    Sale
    Nunn Bush Hartley Chelsea Boot(Men's) -Brown Leather
    Sale
    Nunn Bush Hartley Chelsea Boot(Men's) -Cognac Leather
    Sale
    $66.50
    $95.00 30% off
    Sorel Madson Chelsea Waterproof Boot (Men's)
    New!
    Sale
    Sorel Madson Chelsea Waterproof Boot(Men's) -Black/Black Full Grain Leather
    Sale
    Sorel Madson Chelsea Waterproof Boot(Men's) -Tobacco/Black Full Grain Leather
    Sale
    $120.00
    $160.00 25% off
    Dr. Martens Wilde Low Chelsea Boot (Men's)
    New!
    Sale
    Dr. Martens Wilde Low Chelsea Boot(Men's) -Black Wax Polished Smooth
    Sale
    Dr. Martens Wilde Low Chelsea Boot(Men's) -Cherry Red Antique Temperley
    Sale
    Dr. Martens Wilde Low Chelsea Boot(Men's) -Oak Temperley
    Sale
    $108.95 - $115.95
    $145.00 up to 25% off