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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.
Dr. Martens 2976 Chelsea Boot
New!
Sale
Dr. Martens 2976 Chelsea Boot -Gaucho Crazy Horse
Dr. Martens 2976 Chelsea Boot -Black Inuck
Sale
Dr. Martens 2976 Chelsea Boot -Black Carpathian
Dr. Martens 2976 Chelsea Boot -Black Felix Rub Off Vegan
Dr. Martens 2976 Chelsea Boot -Black Smooth
Dr. Martens 2976 Chelsea Boot -Black Smooth Leather
Dr. Martens 2976 Chelsea Boot -Black Snowplow Water-Resistant
Dr. Martens 2976 Chelsea Boot -Cherry Red Bush
Dr. Martens 2976 Chelsea Boot -Cherry Red Smooth
Dr. Martens 2976 Chelsea Boot -Cherry Red Smooth Leather
Dr. Martens 2976 Chelsea Boot -Cocoa Snowplow Water-Resistant
$119.95 - $154.95
$145.00 - $155.00 up to 17% off
Blundstone Super 550 Series Boot
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Sale
Blundstone Super 550 Series Boot -Antique Brown Leather
Blundstone Super 550 Series Boot -Black
Blundstone Super 550 Series Boot -Black/Red Gore/Red Sole
Blundstone Super 550 Series Boot -Crazy Horse Leather
Blundstone Super 550 Series Boot -Grizzly Brown Leather
Blundstone Super 550 Series Boot -Redwood
Blundstone Super 550 Series Boot -Rustic Black
Blundstone Super 550 Series Boot -Rustic Brown
Blundstone Super 550 Series Boot -Rustic Brown Brogue Leather
Blundstone Super 550 Series Boot -Steel Grey Leather
Blundstone Super 550 Series Boot -Stout Brown/Olive
Blundstone Super 550 Series Boot -Walnut
$189.99 - $199.95
Dr. Martens 101 6-Eye Boot
New!
Sale
Dr. Martens 101 6-Eye Boot -Cherry Red Smooth Standard Leather
Dr. Martens 101 6-Eye Boot -Black Harvest Waxy Soft Leather
Dr. Martens 101 6-Eye Boot -Black Smooth Standard Leather
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 Vintage Smooth Leather
$134.95 - $139.95
Blundstone Dress Series Boot
New!
Sale
Blundstone Dress Series Boot -Black
Blundstone Dress Series Boot -Brown
Blundstone Dress Series Boot -Brown Crazy Horse
Blundstone Dress Series Boot -Rustic Black
Blundstone Dress Series Boot -Rustic Brown
$184.95
Blundstone Thermal Series Boot
New!
Sale
Blundstone Thermal Series Boot -Black Leather
Blundstone Thermal Series Boot -Rustic Brown
$214.95
UGG Baldvin Chelsea Boot (Men's)
New!
Sale
UGG Baldvin Chelsea Boot(Men's) -Chestnut Suede
$199.95
Clarks Bushacre Hill Chelsea Boot (Men's)
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Sale
Clarks Bushacre Hill Chelsea Boot(Men's) -Beeswax Leather
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Clarks Bushacre Hill Chelsea Boot(Men's) -Black Oily Nubuck
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Clarks Bushacre Hill Chelsea Boot(Men's) -Tan Suede
Sale
$78.95 - $93.95
$110.00 up to 28% off
Keen Anchorage III Waterproof Chelsea Boot (Men's)
New!
Sale
Keen Anchorage III Waterproof Chelsea Boot(Men's) -Dark Earth/Mulch
Sale
$111.96
$140.00 20% off
Dr. Martens Work 2976 Chelsea Boot Slip Resistant
New!
Sale
Dr. Martens Work 2976 Chelsea Boot Slip Resistant -Black Industrial Full Grain Leather
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Dr. Martens Work 2976 Chelsea Boot Slip Resistant -Cherry Red Industrial Full Grain Leather
Sale
$119.95
$150.00 20% off
Cole Haan Wagner Grand Chelsea Boot (Men's)
New!
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Cole Haan Wagner Grand Chelsea Boot(Men's) -Midnight Grey Waterproof Nubuck/Textile
Sale
$259.99
$300.00 13% off
Steve Madden Highlyte Chelsea Boot (Men's)
New!
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Steve Madden Highlyte Chelsea Boot(Men's) -Tan Suede
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Steve Madden Highlyte Chelsea Boot(Men's) -Taupe Suede
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Steve Madden Highlyte Chelsea Boot(Men's) -Black Suede
$89.95 - $99.99
$119.95 up to 25% off
Steve Madden Simon Chelsea Boot (Men's)
New!
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Steve Madden Simon Chelsea Boot(Men's) -Black Leather
Sale
Steve Madden Simon Chelsea Boot(Men's) -Brown Leather
Sale
$79.95
$125.00 36% off
Clarks Hinman Chelsea Boot (Men's)
New!
Sale
Clarks Hinman Chelsea Boot(Men's) -Dark Tan Suede
Sale
Clarks Hinman Chelsea Boot(Men's) -Dark Taupe Suede
Sale
$93.95 - $98.99
$110.00 up to 15% off
Frye Lights Chelsea Boot (Men's)
New!
Sale
Frye Lights Chelsea Boot(Men's) -Dark Brown Leather
Sale
$235.99
$278.00 15% off
Skechers Relaxed Fit Rolden Warton Chelsea Boot (Men's)
New!
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Skechers Relaxed Fit Rolden Warton Chelsea Boot(Men's) -Dark Brown
Sale
$78.95
$85.00 7% off
Cole Haan Kennedy Grand Chelsea Waterproof Boot (Men's)
New!
Sale
Cole Haan Kennedy Grand Chelsea Waterproof Boot(Men's) -Black Waterproof Leather
New
Cole Haan Kennedy Grand Chelsea Waterproof Boot(Men's) -Dogwood Nubuck
Sale
$169.95 - $199.95
$200.00 up to 15% off
Dr. Martens Work Fellside SD Chelsea Boot (Men's)
New!
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Dr. Martens Work Fellside SD Chelsea Boot(Men's) -Bark Industrial Bear Tumbled Leather
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Dr. Martens Work Fellside SD Chelsea Boot(Men's) -Black Industrial Full Grain Leather
Sale
$111.95
$140.00 20% off
Danner Mountain 600 Chelsea Boot (Men's)
New!
Sale
Danner Mountain 600 Chelsea Boot(Men's) -Olive Full Grain Leather
Sale
Danner Mountain 600 Chelsea Boot(Men's) -Black Full Grain Leather
Danner Mountain 600 Chelsea Boot(Men's) -Mahogany Full Grain Leather
Danner Mountain 600 Chelsea Boot(Men's) -Saddle Tan Full Grain Leather
$127.95 - $169.95
$169.95 - $170.00 up to 25% off