Phone
    Call
    1 (888) 200 - 8414
    Mon - Fri: 8:00 AM - Midnight ET
    Sat - Sun: 8:00 AM - 11:00 PM ET

    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.
    1-36 of 110 results
     1 2 3 4 
    Sort by
    Display
    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
    Dr. Martens 2976 Chelsea Boot
    New!
    Sale
    Dr. Martens 2976 Chelsea Boot -Charro/Dark Brown Brando/Hi Suede Waterproof
    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
    Dr. Martens 2976 Chelsea Boot -Black Smooth Leather
    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 -Gaucho Crazy Horse
    $73.00 - $144.95
    $145.00 up to 50% off
    Keen Anchorage III Waterproof Chelsea Boot (Men's)
    New!
    Sale
    Keen Anchorage III Waterproof Chelsea Boot(Men's) -Black/Raven
    Sale
    Keen Anchorage III Waterproof Chelsea Boot(Men's) -Dark Earth/Mulch
    Sale
    $94.50
    $135.00 30% off
    Bearpaw Marcus Chelsea Boot (Men's)
    New!
    Sale
    Bearpaw Marcus Chelsea Boot(Men's) -Black II Suede
    Sale
    Bearpaw Marcus Chelsea Boot(Men's) -Hickory II Suede
    Sale
    $59.99
    $69.99 14% off
    Dr. Martens 101 6-Eye Boot
    New!
    Sale
    Dr. Martens 101 6-Eye Boot -Black Harvest Waxy Soft Leather
    New
    Dr. Martens 101 6-Eye Boot -Black Smooth Leather/Chelsea Zip-Up
    New
    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 -Tan Harvest Waxy Soft Leather
    New
    Dr. Martens 101 6-Eye Boot -White Smooth Leather
    $134.95 - $144.95
    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) -Tobacco 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
    Clarks Bushacre Hill Chelsea Boot (Men's)
    New!
    Sale
    Clarks Bushacre Hill Chelsea Boot(Men's) -Beeswax Leather
    Sale
    Clarks Bushacre Hill Chelsea Boot(Men's) -Black Oily Nubuck
    Sale
    $93.50
    $110.00 15% off
    Dr. Martens Fusion Steel Toe Chelsea Boot
    New!
    Sale
    Dr. Martens Fusion Steel Toe Chelsea Boot -Bark Industrial Bear Leather
    Sale
    Dr. Martens Fusion Steel Toe Chelsea Boot -Black Industrial Full Grain Leather
    Sale
    $124.95
    $135.00 7% off
    Clarks Desert Peak Chelsea Boot (Men's)
    New!
    Sale
    Clarks Desert Peak Chelsea Boot(Men's) -Beeswax Cow Full Grain Leather
    Sale
    Clarks Desert Peak Chelsea Boot(Men's) -Black Cow Full Grain Leather
    Sale
    $124.95
    $150.00 17% off
    Clarks Hinman Chelsea Boot (Men's)
    New!
    Sale
    Clarks Hinman Chelsea Boot(Men's) -Dark Tan Suede
    Sale
    $93.50
    $110.00 15% off