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    Best Seller
    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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    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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    Best Seller
    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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    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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    Anthropologie Shoes | Anthropologie 6 Grey Stretch Suede Otk Over The Knee Boots | Color: Gray/Tan | Size: 6

    Anthropologie Shoes | Anthropologie 6 Grey Stretch Suede Otk Over The Knee Boots | Color: Gray/Tan | Size: 6

    Anthropologie Grey Stretch Suede Tie-Back Over-The-Knee Otk Boots (With Partial Side Zipper Closure; Stacked Chunky Heel) Size: Us 6 Color: Light Grey New In Box Timeless, Versatile Neutral Tone. Stretchy Material Accommodates A Range Of Calf/Leg/Thigh... more

    $130.00

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    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

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    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

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    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

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    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 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 - 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 - 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 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 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 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 - 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 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 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 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 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 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 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 - 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 - 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 - 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 - 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 - 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 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 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 - 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 Vance Co. Marshall Chelsea Boot - Grey - 12

    Vance Co. Shoes Vance Co. Marshall Chelsea Boot - Grey - 12

    This boot by Vance Co. will work overtime for you, as you wear it to the office, the store, and everywhere else. The Marshall is an iconic Chelsea silhouette with a pull-tab and stretch goring on either side. This wear-it-everywhere look is made with... more

    $69.99

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    Vance Co. Shoes Vance Co. Marshon Chelsea Boot - Grey - 8.5

    Vance Co. Shoes Vance Co. Marshon Chelsea Boot - Grey - 8.5

    With a 6 mm Tru Comfort Foamâ„¢ insole, this classic boot is sure to be a home run. The Marshon by Vance Co. is a classic Chelsea boot with stretch gore panels and vegan leather uppers. A durable rubber sole and pull-tab at the ankle finish the design.... more

    $64.99

    go to store
    Vance Co. Shoes Vance Co. Marshall Wide Width Chelsea Boot - Grey - 8

    Vance Co. Shoes Vance Co. Marshall Wide Width Chelsea Boot - Grey - 8

    This chelsea boot by Vance Co. will work overtime for you, as you wear it to work, while running errands, and everywhere else. The Marshall is an iconic round-toe silhouette with a wide-width footbed and stretch gore on either side for the perfect fit.... more

    $69.99

    go to store
    Thomas and Vine Thomas & Vine Jaylon Cap Toe Chelsea Boot - Grey - 11.5

    Thomas and Vine Thomas & Vine Jaylon Cap Toe Chelsea Boot - Grey - 11.5

    Ready to accompany you at a moment's notice, the Jaylon by Thomas & Vine. This classic chelsea boot features genuine leather uppers cleverly detailed with a cap-toe design. A flexible EVA sole, stretch gore accents, and an 8 mm Tru Comfort Foamâ„¢... more

    $129.99

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    Vance Co. Shoes Vance Co. Marshon Chelsea Boot - Grey - 8

    Vance Co. Shoes Vance Co. Marshon Chelsea Boot - Grey - 8

    With a 6 mm Tru Comfort Foamâ„¢ insole, this classic boot is sure to be a home run. The Marshon by Vance Co. is a classic Chelsea boot with stretch gore panels and vegan leather uppers. A durable rubber sole and pull-tab at the ankle finish the design.... more

    $64.99

    go to store

    More information about Men's Shoes

    Best prices on Paige boots chelsea boots chunky, 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.