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    Best Seller
    Madewell Shoes | New Madewell The Carina Snake Embossed Leather Low Chelsea Ankle Boots A775 | Color: Cream/Gray | Size: 6

    Madewell Shoes | New Madewell The Carina Snake Embossed Leather Low Chelsea Ankle Boots A775 | Color: Cream/Gray | Size: 6

    New Occasion Business, Casual Calf Width Regular Character Boots Color Multicolor Toe Shape Pointed Toe Closure Pull On Accents Stone Style Chelsea Features Stretch Season Winter, Fall, Spring Shoe Shaft Style Ankle Pattern Animal Print Lining Material... more

    $81.00

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    Madewell Shoes | Madewell Laura Chelsea Real Fur Dyed Spotted Calf Hair Hilty Block Boots Size 7 | Color: Brown/Tan | Size: 7

    Madewell Shoes | Madewell Laura Chelsea Real Fur Dyed Spotted Calf Hair Hilty Block Boots Size 7 | Color: Brown/Tan | Size: 7

    Madewell Laura Chelsea Real Fur Dyed Spotted Calf Hair Hilty Block Boots Size 7 Brand: Madewell Size: 7 Color: Tan And Brown Pattern: Leopard Material: Leather Condition: Preloved, In Good Condition, Stretch Band Shows Minimal Features: Slip On Closure... more

    $125.00

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    Best Seller
    Timberland Redwood Falls Chelsea - Mens 11 Tan Boot Medium

    Timberland Redwood Falls Chelsea - Mens 11 Tan Boot Medium

    *Waterproof Better Leather upper from an LWG silver-rated tannery *Pull-on styling with dual stretch gore *ReBOTL fabric lining *OrthoLite footbed *Gripstick rubber outsole with patented L7 design features multi-directional leading edges with beveled... more

    $129.95

    FREE shipping

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    Timberland Redwood Falls Chelsea - Mens 11.5 Tan Boot Medium

    Timberland Redwood Falls Chelsea - Mens 11.5 Tan Boot Medium

    *Waterproof Better Leather upper from an LWG silver-rated tannery *Pull-on styling with dual stretch gore *ReBOTL fabric lining *OrthoLite footbed *Gripstick rubber outsole with patented L7 design features multi-directional leading edges with beveled... more

    $129.95

    FREE shipping

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    Michael Kors Shoes | Michael Kors Sofie Leather W/ Silver Studs Boots Bootie Western Stiletto Sz 9 | Color: Black/Silver | Size: 9

    Michael Kors Shoes | Michael Kors Sofie Leather W/ Silver Studs Boots Bootie Western Stiletto Sz 9 | Color: Black/Silver | Size: 9

    Worn Twice, In Perfect Condition Michael Kors Sofie Black Leather With Silver Studds Shoe Booties, Size 9 Black Leather With Elastic Gored Stretch Sides - Slip On, Closed Pointed Toe, Slim Stiletto Heel - Approx: 4 3/4"., 1 1/4" Platform more

    $95.00

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    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 13

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 13

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 8

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 8

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 8

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 8

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 11.5

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 11.5

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 11

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 11

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 10.5

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 10.5

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 8.5

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 8.5

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 10.5

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 10.5

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 9.5

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 9.5

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 8.5

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 8.5

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 9.5

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 9.5

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 9

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 9

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 10

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 10

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 10.5

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 10.5

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 11

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 11

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 9

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 9

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 9

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 9

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 12

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 12

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 13

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 13

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 9.5

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 9.5

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 12

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 12

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 8.5

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 8.5

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 10

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 10

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 8

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 8

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 11.5

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 11.5

    The Yellowstone boot by Territory is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a forgiving fit. A 6 mm Tru Comfort Foamâ„¢ insole paired with an... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 11.5

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 11.5

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 12

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Grey - 12

    Territory's Yellowstone hiking boot is ready to pull on and go whenever adventure calls. This water-resistant genuine leather boot features stretch gore at the ankles for easy entry and a wide-width footbed for a roomy fit. An EVA/Rubber sole paired... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 11

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 11

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 13

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 13

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 10

    Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 10

    Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more

    $119.99

    go to store
    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Grey - 9.5

    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Grey - 9.5

    Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more

    $69.99

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    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Grey - 10

    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Grey - 10

    Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more

    $69.99

    go to store
    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Grey - 9

    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Grey - 9

    Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more

    $69.99

    go to store
    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Grey - 8

    Vance Co. Shoes Thorpe Wingtip Chelsea Boot - Grey - 8

    Introducing the Thorpe chelsea boot by Vance Co. These suave boots are made with premium vegan leather for an upscale look. With a comfortable 12 mm Tru Comfort Foamâ„¢ insole and a convenient pull-on silhouette with stretch gore accents, they offer... more

    $69.99

    go to store
    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Grey - 12

    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Grey - 12

    The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more

    $69.99

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    More information about Men's Shoes

    Best prices on Laguna platform leather chelsea boots, Stretchable, Gray in Men's Shoes online. Visit Bizrate to find the best deals on top brands. Read reviews on Clothing & Accessories merchants and buy with confidence.