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HomeMen's ShoesBoots

Men's Chelsea Boots

A hardworking style that’s perfect for work and play, men’s Chelsea boots are a classic for a reason. Leather or suede Chelsea boots take you from boardroom to bar in an instant, proving their versatility. If your wardrobe has a gap in it, fill it with a pair of these gusseted boots.

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    54 Results
    Drover Black Leather Chelsea Boots
    COLORADO
    Drover Black Leather Chelsea Boots
    $229.95
    Second Pair 1/2 Price
    Mills Black Leather Ankle Boots
    COLORADO
    Mills Black Leather Ankle Boots
    $199.95
    Second Pair 1/2 Price
    Mills Tan Leather Ankle Boots
    COLORADO
    Mills Tan Leather Ankle Boots
    $199.95
    Second Pair 1/2 Price
    53% OFF
    Brumby Brown Leather
    COLORADO
    Brumby Brown Leather
    $89.00
    $189.95
    Second Pair 1/2 Price
    24% OFF
    League Cognac Leather Chelsea Boots
    HUSH PUPPIES
    League Cognac Leather Chelsea Boots
    $159.00
    $209.95
    Second Pair 1/2 Price
    55% OFF
    Pointer Brown Leather Chelsea Boots
    Last Pairs
    ROCKPORT
    Pointer Brown Leather Chelsea Boots
    $119.00
    $269.95
    Second Pair 1/2 Price
    Ritter Dark Tan Tumble Leather Chelsea Boots
    COLORADO
    Ritter Dark Tan Tumble Leather Chelsea Boots
    $199.95
    Second Pair 1/2 Price
    York 22 Olmo Leather Chelsea Boots
    PIKOLINOS
    York 22 Olmo Leather Chelsea Boots
    $349.95
    Second Pair 1/2 Price
    JOIN THE CLUB
    Ritter Brown Leather Chelsea Boots
    COLORADO
    Ritter Brown Leather Chelsea Boots
    $199.95
    Second Pair 1/2 Price
    York 22 Cuero Leather Chelsea Boots
    PIKOLINOS
    York 22 Cuero Leather Chelsea Boots
    $349.95
    Second Pair 1/2 Price
    60% OFF
    FINAL SALE
    Chisel Brown Leather Chelsea Boots
    Last Pairs
    COLORADO
    Chisel Brown Leather Chelsea Boots
    $79.00
    $199.95
    Second Pair 1/2 Price
    Volga Black Leather Chelsea Boots
    ROCKPORT
    Volga Black Leather Chelsea Boots
    $249.95
    Second Pair 1/2 Price
    Rodeo Black Leather Chelsea Boots
    COLORADO
    Rodeo Black Leather Chelsea Boots
    $229.95
    Second Pair 1/2 Price
    Bunbury Black Leather Chelsea Boots
    WILD RHINO
    Bunbury Black Leather Chelsea Boots
    $249.95
    Second Pair 1/2 Price
    Bunbury Brown Leather Chelsea Boots
    WILD RHINO
    Bunbury Brown Leather Chelsea Boots
    $249.95
    Second Pair 1/2 Price
    Earl Black Leather Chelsea Boots
    WILD RHINO
    Earl Black Leather Chelsea Boots
    $239.95
    Second Pair 1/2 Price
    JOIN THE CLUB
    Plaid Rust Leather Chelsea Boots
    WILD RHINO
    Plaid Rust Leather Chelsea Boots
    $269.95
    Second Pair 1/2 Price
    Volga Tan Leather Chelsea Boots
    ROCKPORT
    Volga Tan Leather Chelsea Boots
    $249.95
    Second Pair 1/2 Price
    Rodeo Brown Leather Chelsea Boots
    COLORADO
    Rodeo Brown Leather Chelsea Boots
    $229.95
    Second Pair 1/2 Price
    60% OFF
    FINAL SALE
    U Tiberio A Coffee Leather Chelsea Boots
    Last Pairs
    GEOX
    U Tiberio A Coffee Leather Chelsea Boots
    $129.00
    $329.95
    Second Pair 1/2 Price
    Volga Brown Leather Chelsea Boots
    ROCKPORT
    Volga Brown Leather Chelsea Boots
    $249.95
    Second Pair 1/2 Price
    Rancher Black Leather Chelsea Boots
    WILD RHINO
    Rancher Black Leather Chelsea Boots
    $249.95
    Second Pair 1/2 Price
    Earl Cognac Leather Chelsea Boots
    WILD RHINO
    Earl Cognac Leather Chelsea Boots
    $239.95
    Second Pair 1/2 Price
    Drover Brown Leather Chelsea Boots
    COLORADO
    Drover Brown Leather Chelsea Boots
    $229.95
    Second Pair 1/2 Price
    JOIN THE CLUB
    Braga Dark Brown Leather Chelsea Boots
    COLORADO
    Braga Dark Brown Leather Chelsea Boots
    $199.95
    Second Pair 1/2 Price
    Plaid Black Leather Chelsea Boots
    WILD RHINO
    Plaid Black Leather Chelsea Boots
    $269.95
    Second Pair 1/2 Price
    Braga Black Leather Chelsea Boots
    COLORADO
    Braga Black Leather Chelsea Boots
    $199.95
    Second Pair 1/2 Price
    Rancher Cognac Leather Chelsea Boots
    WILD RHINO
    Rancher Cognac Leather Chelsea Boots
    $249.95
    Second Pair 1/2 Price
    Rancher Dark Brown Leather Chelsea Boots
    Last Pairs
    WILD RHINO
    Rancher Dark Brown Leather Chelsea Boots
    $249.95
    Second Pair 1/2 Price
    Faraday Tan Leather Chelsea Boots
    WILD RHINO
    Faraday Tan Leather Chelsea Boots
    $229.95
    Second Pair 1/2 Price
    Mills Chestnut Leather Chelsea Boots
    COLORADO
    Mills Chestnut Leather Chelsea Boots
    $199.95
    Second Pair 1/2 Price
    Gravel Chestnut Suede Chelsea Boots
    HUSH PUPPIES
    Gravel Chestnut Suede Chelsea Boots
    $209.95
    Second Pair 1/2 Price
    JOIN THE CLUB
    Alpha Dark Brown Leather Chelsea Boots
    COLORADO CRAFTSMAN
    Alpha Dark Brown Leather Chelsea Boots
    $199.95
    Second Pair 1/2 Price
    Porter Black Leather Chelsea Boots
    COLORADO
    Porter Black Leather Chelsea Boots
    $229.95
    Second Pair 1/2 Price
    Gravel Ground Coffee Suede Chelsea Boots
    HUSH PUPPIES
    Gravel Ground Coffee Suede Chelsea Boots
    $209.95
    Second Pair 1/2 Price
    Porter Chestnut Leather Chelsea Boots
    COLORADO
    Porter Chestnut Leather Chelsea Boots
    $229.95
    Second Pair 1/2 Price
    Flip Brown Leather Chelsea Boots
    WILD RHINO
    Flip Brown Leather Chelsea Boots
    $229.95
    Second Pair 1/2 Price
    Alpha Black Leather Elastic Gusset Chelsea Boots
    COLORADO CRAFTSMAN
    Alpha Black Leather Elastic Gusset Chelsea Boots
    $199.95
    Second Pair 1/2 Price
    Driscoe Dark Brown Leather Chelsea Boots
    COLORADO
    Driscoe Dark Brown Leather Chelsea Boots
    $199.95
    Second Pair 1/2 Price
    Ritter Black Tumble Leather Chelsea Boots
    COLORADO
    Ritter Black Tumble Leather Chelsea Boots
    $199.95
    Second Pair 1/2 Price
    Ritter Tan Leather Boots
    COLORADO
    Ritter Tan Leather Boots
    $199.95
    Second Pair 1/2 Price
    Alpha Cognac Leather Chelsea Boots
    COLORADO CRAFTSMAN
    Alpha Cognac Leather Chelsea Boots
    $199.95
    Second Pair 1/2 Price
    Porter Dark Tan Leather Chelsea Boots
    COLORADO
    Porter Dark Tan Leather Chelsea Boots
    $229.95
    Second Pair 1/2 Price
    Chelsea Leon Desert Suede Chelsea Boots
    Last Pairs
    ROLLIE
    Chelsea Leon Desert Suede Chelsea Boots
    $329.95
    Second Pair 1/2 Price
    55% OFF
    Pointer Tan Leather Chelsea Boots
    ROCKPORT
    Pointer Tan Leather Chelsea Boots
    $119.00
    $269.95
    Second Pair 1/2 Price
    24% OFF
    League Black Leather Chelsea Boots
    HUSH PUPPIES
    League Black Leather Chelsea Boots
    $159.00
    $209.95
    Second Pair 1/2 Price
    60% OFF
    FINAL SALE
    Erroll 51 Schwarz Nubuck Chelsea Boots
    JOSEF SEIBEL
    Erroll 51 Schwarz Nubuck Chelsea Boots
    $99.00
    $249.95
    Second Pair 1/2 Price
    60% OFF
    FINAL SALE
    Chisel Black Leather Chelsea Boots
    Last Pairs
    COLORADO
    Chisel Black Leather Chelsea Boots
    $79.00
    $199.95
    Second Pair 1/2 Price