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    Discount Mens Casual Chelsea Boots

    1-29 of 29 results
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    Blundstone Super 550 Series Boot
    New!
    Sale
    Blundstone Super 550 Series Boot -Black
    Sale
    Blundstone Super 550 Series Boot -Burgundy
    Sale
    Blundstone Super 550 Series Boot -Rustic Black
    Sale
    Blundstone Super 550 Series Boot -Rustic Brown
    Sale
    Blundstone Super 550 Series Boot -Rustic Brown/Brown Gore/Gum Sole
    Sale
    Blundstone Super 550 Series Boot -Walnut
    Sale
    $135.95 - $199.95
    $199.95 up to 32% off
    Dr. Martens 101 6-Eye Boot
    New!
    Sale
    Dr. Martens 101 6-Eye Boot -Black Harvest Waxy Soft Leather
    Sale
    Dr. Martens 101 6-Eye Boot -Black Smooth Leather/Chelsea Zip-Up
    Sale
    Dr. Martens 101 6-Eye Boot -Cherry Red Smooth
    Sale
    Dr. Martens 101 6-Eye Boot -White Smooth Leather
    Sale
    $73.97 - $139.95
    $135.00 - $145.00 up to 45% off
    Dr. Martens 2976 Chelsea Boot
    New!
    Sale
    Dr. Martens 2976 Chelsea Boot -Cherry Red Antique Temperley
    Sale
    $114.95 - $145.00
    $145.00 up to 21% off
    Rockport Wynstin Chelsea Boot (Men's)
    New!
    Sale
    Rockport Wynstin Chelsea Boot(Men's) -Black Leather
    Sale
    $64.97 - $130.00
    $130.00 up to 50% off
    Clarks Bushacre Hill Chelsea Boot (Men's)
    New!
    Sale
    Clarks Bushacre Hill Chelsea Boot(Men's) -Black Oily Nubuck
    Sale
    $77.00 - $109.95
    $110.00 up to 30% off
    Wolverine Bedford Soft Toe Chelsea Boot (Men's)
    New!
    Sale
    Wolverine Bedford Soft Toe Chelsea Boot(Men's) -Black Full Grain Leather
    Sale
    Wolverine Bedford Soft Toe Chelsea Boot(Men's) -Brown Full Grain Leather
    Sale
    $88.99
    $115.00 23% off
    Dr. Martens Oakford Chelsea Boot (Men's)
    New!
    Sale
    Dr. Martens Oakford Chelsea Boot(Men's) -Tan Grizzly
    Sale
    $62.97 - $114.95
    $115.00 up to 45% off
    Clarks Desert Peak Chelsea Boot (Men's)
    New!
    Sale
    Clarks Desert Peak Chelsea Boot(Men's) -Black Cow Full Grain Leather
    Sale
    $124.95 - $149.95
    $150.00 up to 17% off
    Dr. Martens Fellside SD Chelsea Boot (Men's)
    New!
    Sale
    Dr. Martens Fellside SD Chelsea Boot(Men's) -Bark Industrial Bear Tumbled Leather
    Sale
    Dr. Martens Fellside SD Chelsea Boot(Men's) -Black Industrial Full Grain Leather
    Sale
    $105.00 - $129.95
    $140.00 up to 25% off
    Dr. Martens Howden Chelsea Work Boot
    New!
    Sale
    Dr. Martens Howden Chelsea Work Boot -Black Industrial Bear Tumbled Leather
    Sale
    $134.95
    $145.00 7% 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
    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
    $41.95
    $69.99 40% off
    Florsheim Limited Indie Gore Boot (Men's)
    New!
    Sale
    Florsheim Limited Indie Gore Boot(Men's) -Chocolate Smooth Leather
    Sale
    $87.97
    $175.00 50% off
    Florsheim Casey Gore Boot (Men's)
    New!
    Sale
    Florsheim Casey Gore Boot(Men's) -Black Leather
    Sale
    Florsheim Casey Gore Boot(Men's) -Cognac Leather
    Sale
    $89.95
    $120.00 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
    $126.97
    $230.00 45% 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
    Frye Sam Chelsea Boot (Men's)
    New!
    Sale
    Frye Sam Chelsea Boot(Men's) -Black Leather
    Sale
    $199.95
    $298.00 33% 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
    Dr. Martens Lyme Chelsea Boot (Men's)
    New!
    Sale
    Dr. Martens Lyme Chelsea Boot(Men's) -Dark Brown Grizzly
    Sale
    Dr. Martens Lyme Chelsea Boot(Men's) -Navy Bronx Suede
    Sale
    Dr. Martens Lyme Chelsea Boot(Men's) -Tan Slippery Waterproof Nubuck Leather
    Sale
    $54.97 - $119.95
    $110.00 - $120.00 up to 50% off
    Dr. Martens Harper Chelsea (Men's)
    New!
    Sale
    Dr. Martens Harper Chelsea(Men's) -Dark Gull Grey Nylon
    Sale
    $90.00
    $120.00 25% off
    Dr. Martens Wilde Low Chelsea Boot (Men's)
    New!
    Sale
    Dr. Martens Wilde Low Chelsea Boot(Men's) -Oak Temperley
    Sale
    $79.97
    $145.00 45% off