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    Best Seller
    Madewell Shoes | Madewell Size 8.5 The Carlin Shearling Chelsea Boot Ankle Boot Suede Rugged | Color: Tan | Size: 8.5

    Madewell Shoes | Madewell Size 8.5 The Carlin Shearling Chelsea Boot Ankle Boot Suede Rugged | Color: Tan | Size: 8.5

    Madewell Size 8.5 The Carlin Shearling Chelsea Boot Ankle Boot Suede Rugged Made Of Water-Resistant Suede With A Rugged Lug Sole, These Pull-On Chelsea Boots Are Fully Lined In Real Shearling To Up The Cozy Factor. Basically: All-Weather Boots You'll... more

    $97.00

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    J. Crew Shoes | J Crew Rain Ankle Boots Short Lug Sole Chelsea Nutmeg Zara Madewell Loft Mk 8.0 | Color: Brown/Tan | Size: 8

    J. Crew Shoes | J Crew Rain Ankle Boots Short Lug Sole Chelsea Nutmeg Zara Madewell Loft Mk 8.0 | Color: Brown/Tan | Size: 8

    J Crew 8.0 Fits Tts Do Not Run Small Or Narrow Nutmeg Brown Tan Worn Once Excellent Condition Pet Free Vegan Home Extremely Comfortable With Padded Support Insole , Soft Waterproof Upper And Elastic Pull On Very Well Made I Own 3 Pair Of This Boot And... more

    $35.00

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    Best Seller
    Madewell Shoes | Madewell Black Rubber Chelsea Rain Waterproof Ankle Boots Size 7 | Color: Black | Size: 7

    Madewell Shoes | Madewell Black Rubber Chelsea Rain Waterproof Ankle Boots Size 7 | Color: Black | Size: 7

    Madewell Black Chelsea Rain Waterproof Ankle Boots Size 7 Smoke Free Home Bundle For A Discount more

    $54.00

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    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 13 LDB-STL-BRN-130

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 13 LDB-STL-BRN-130

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 13 LDB-STL-BRN-130. The Legacy Chelsea features the same Commercial Grade performance and safety features of the classic Legacy Boot but with functional pull tabs and a twin elastic gore for... more

    $155.00

    FREE shipping

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    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 8 LDB-STL-BRN-080

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 8 LDB-STL-BRN-080

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 8 LDB-STL-BRN-080. The Legacy Chelsea features the same Commercial Grade performance and safety features of the classic Legacy Boot but with functional pull tabs and a twin elastic gore for... more

    $155.00

    FREE shipping

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    Matte Puddle Chelsea Boots

    Matte Puddle Chelsea Boots

    Men's Bottega Veneta Matte Puddle Chelsea Boots - Green - Casual boots Ankle-high waterproof rubber Chelsea boots in matte green. more

    $820.00

    FREE shipping

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    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 8 LDB-STL-BRN-080

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 8 LDB-STL-BRN-080

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 8 LDB-STL-BRN-080. The Legacy Chelsea features the same Commercial Grade performance and safety features of the classic Legacy Boot but with functional pull tabs and a twin elastic gore for... more

    $155.00

    FREE shipping

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    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 9 LDB-STL-BRN-090

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 9 LDB-STL-BRN-090

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 9 LDB-STL-BRN-090. The Legacy Chelsea features the same Commercial Grade performance and safety features of the classic Legacy Boot but with functional pull tabs and a twin elastic gore for... more

    $155.00

    FREE shipping

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    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 9 LDB-STL-BRN-090

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 9 LDB-STL-BRN-090

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 9 LDB-STL-BRN-090. The Legacy Chelsea features the same Commercial Grade performance and safety features of the classic Legacy Boot but with functional pull tabs and a twin elastic gore for... more

    $155.00

    FREE shipping

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    Off- Stride Boots

    Off- Stride Boots

    Men's Bottega Veneta Off- Stride Boots - Black - Casual boots Ankle-high waterproof rubber Chelsea boots in off-white. more

    $650.00

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    Tan Bower-evab Boots

    Tan Bower-evab Boots

    Men's Suicoke Tan Bower-evab Boots - Black - Casual boots Ankle-high waterproof quilted 3MTM THINSULATETM insulated ripstop Chelsea boots in tan. Faux-leather trim throughout. more

    $345.00 $242.00

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    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

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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 - Brown - 10

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Brown - 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

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    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 12 LDB-STL-BRN-120

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 12 LDB-STL-BRN-120

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 12 LDB-STL-BRN-120. The Legacy Chelsea features the same Commercial Grade performance and safety features of the classic Legacy Boot but with functional pull tabs and a twin elastic gore for... more

    $155.00

    FREE shipping

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    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 11 LDB-STL-BRN-110

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 11 LDB-STL-BRN-110

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 11 LDB-STL-BRN-110. The Legacy Chelsea features the same Commercial Grade performance and safety features of the classic Legacy Boot but with functional pull tabs and a twin elastic gore for... more

    $155.00

    FREE shipping

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    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 14 LDB-STL-BRN-140

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 14 LDB-STL-BRN-140

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 14 LDB-STL-BRN-140. The Legacy Chelsea features the same Commercial Grade performance and safety features of the classic Legacy Boot but with functional pull tabs and a twin elastic gore for... more

    $155.00

    FREE shipping

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    Carhartt Shoes | Carhartt Men's 10.5 Millbrook Romeo Black Soft-Toe Chelsea Wedge Boots Fm4021-M | Color: Black | Size: 10.5

    Carhartt Shoes | Carhartt Men's 10.5 Millbrook Romeo Black Soft-Toe Chelsea Wedge Boots Fm4021-M | Color: Black | Size: 10.5

    Carhartt Men's 10.5 Millbrook Romeo Black Soft-Toe Chelsea Wedge Boots Fm4021-M A Pair Of Men's Carhartt Millbrook Water Resistant Wr 4" Romeo Black Oiled Leather Wedge Pull-On Chelsea Ankle Work Soft-Toe Boots. Size: 10.5 Width: M, D, Medium New... more

    $175.00

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

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 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

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    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 - Brown - 8.5

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

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

    Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Brown - 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 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 - Black - 12

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Black - 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 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 - Brown - 11.5

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

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

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

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

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

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

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

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

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

    Territory Boots Territory Yellowstone Water Resistant Wide Width Chelsea Boot - Brown - 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 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

    More information about Men's Shoes

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