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    Discount Mens Casual Chelsea Boots

    1-33 of 33 results
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    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
    $109.95 - $144.95
    $145.00 up to 24% off
    Blundstone Super 550 Series Boot
    New!
    Sale
    Blundstone Super 550 Series Boot -Steel Grey/Black Gore
    Sale
    $135.95 - $194.95
    $194.95 up to 30% 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) -Tobacco Suede
    Sale
    $144.50 - $169.95
    $170.00 up to 15% 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 Lyme Chelsea Boot (Men's)
    New!
    Sale
    Dr. Martens Lyme Chelsea Boot(Men's) -Black Slippery Waterproof Nubuck Leather
    Sale
    Dr. Martens Lyme Chelsea Boot(Men's) -Navy Bronx Suede
    Sale
    $87.95 - $119.95
    $110.00 - $120.00 up to 20% off
    Cole Haan Grantland Waterproof Chelsea Boot (Men's)
    New!
    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
    Cole Haan Grantland Waterproof Chelsea Boot(Men's) -Woodbury Waterproof Leather
    Sale
    $180.95
    $240.00 25% off
    ECCO Turn GORE-TEX Chelsea Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Chelsea Boot(Men's) -Mocha Cow Oil Nubuck
    Sale
    $206.95
    $230.00 10% off
    Caterpillar Pelton Chelsea Boot (Men's)
    New!
    Sale
    Caterpillar Pelton Chelsea Boot(Men's) -Dark Beige Full Grain Leather
    Sale
    $97.95
    $129.95 25% 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
    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 Howden Chelsea Work Boot
    New!
    Sale
    Dr. Martens Howden Chelsea Work Boot -Black Industrial Bear Tumbled Leather
    Sale
    $108.75
    $145.00 25% 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
    $101.25
    $135.00 25% 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
    Nunn Bush Hampton Plain Toe Twin Gore Boot (Men's)
    New!
    Sale
    Nunn Bush Hampton Plain Toe Twin Gore Boot(Men's) -Black Leather
    Sale
    Nunn Bush Hampton Plain Toe Twin Gore Boot(Men's) -Brown Leather
    Sale
    $75.95
    $95.00 20% 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
    Dockers Stanwell Plain Toe Chelsea Boot (Men's)
    New!
    Sale
    Dockers Stanwell Plain Toe Chelsea Boot(Men's) -Black Oily Tumbled Full Grain
    Sale
    Dockers Stanwell Plain Toe Chelsea Boot(Men's) -Chocolate Oily Tumbled Full Grain
    Sale
    Dockers Stanwell Plain Toe Chelsea Boot(Men's) -Dark Tan Burnished Crazyhorse
    Sale
    $69.99
    $90.00 22% off
    Sperry Top-Sider Dockyard Chelsea Boot (Men's)
    New!
    Sale
    Sperry Top-Sider Dockyard Chelsea Boot(Men's) -Navy Leather
    Sale
    Sperry Top-Sider Dockyard Chelsea Boot(Men's) -Tan Leather
    Sale
    $127.50
    $149.95 15% off
    Sperry Top-Sider Wahoo Chelsea Boot (Men's)
    New!
    Sale
    Sperry Top-Sider Wahoo Chelsea Boot(Men's) -Noce Suede
    Sale
    $66.95
    $74.95 11% 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
    Florsheim Rockit Buckle Boot (Men's)
    New!
    Sale
    Florsheim Rockit Buckle Boot(Men's) -Brown Leather
    Sale
    Florsheim Rockit Buckle Boot(Men's) -Black Leather
    Sale
    $100.95
    $135.00 25% off
    Frye Sam Chelsea Boot (Men's)
    New!
    Sale
    Frye Sam Chelsea Boot(Men's) -Black Leather
    Sale
    $199.95
    $298.00 33% 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 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
    G.H. Bass & Co. Hendrick Chelsea Boot (Men's)
    New!
    Sale
    G.H. Bass & Co. Hendrick Chelsea Boot(Men's) -Dark Brown Leather
    Sale
    $119.99
    $150.00 20% off
    Florsheim Limited Indie Gore Boot (Men's)
    New!
    Sale
    Florsheim Limited Indie Gore Boot(Men's) -Black Milled Leather
    Sale
    Florsheim Limited Indie Gore Boot(Men's) -Chocolate Smooth Leather
    Sale
    Florsheim Limited Indie Gore Boot(Men's) -Toffee Milled Leather
    Sale
    $122.95 - $130.95
    $175.00 up to 30% off
    Ariat Recon Mid Chelsea Boot (Men's)
    New!
    Sale
    Ariat Recon Mid Chelsea Boot(Men's) -Golden Grizzly Full Grain Leather
    Sale
    $119.95
    $139.95 14% off
    Florsheim Casey Gore Boot (Men's)
    New!
    Sale
    Florsheim Casey Gore Boot(Men's) -Black Leather
    Sale
    $89.95
    $120.00 25% off