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    Best Seller
    Daily Double Chelsea Boot

    Daily Double Chelsea Boot

    Men's Eastland Daily Double Chelsea Boot - Brown - Casual boots Dual pull-tabs and stretchy gore insets lend easy wear to a rich leather Chelsea boot grounded by a cushioned footbed for lasting comfort. more

    $125.00

    FREE shipping

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    Cyrus Chelsea Boot

    Cyrus Chelsea Boot

    Men's Eastland Cyrus Chelsea Boot - Black - Casual boots Get inspired by the classiness of the Cyrus Chelsea boot by Eastland. Dual gores on the sides of the pull-on boot offer a comfortable fit while the aux leather sole absorbs shocks while keeping... more

    $84.99

    FREE shipping

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    Best Seller
    Port Chalmers Chelsea Boot

    Port Chalmers Chelsea Boot

    Men's Rodd & Gunn Port Chalmers Chelsea Boot - Brown - Casual boots Stretchy side panels mean easy entry into this versatile and stylish Chelsea boot crafted from burnished European leather. Pull-on style with elastic gore insets Leather and textile... more

    $238.00

    FREE shipping

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    Free People Shoes | Free People Atlas Textile Chelsea Ankle Boots | Color: Black/Blue | Size: 38eu

    Free People Shoes | Free People Atlas Textile Chelsea Ankle Boots | Color: Black/Blue | Size: 38eu

    Rounded Toes ~ Ankle Height Shaft ~ Dual/Two Stretchy Gore Panels On The Sides Of The Ankle Shafts ~ Leather Panels On Toes And Heels ... With Scalloped Leather Trims Trimming The Gore/Stretch Panels ~ Woven Textile Panels On Top Of The Foot And On The... more

    $72.00

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    Madewell Shoes | Madewell Size 6 The Benning Chelsea Boot In Warm Cinnamon | Color: Brown/Tan | Size: 6

    Madewell Shoes | Madewell Size 6 The Benning Chelsea Boot In Warm Cinnamon | Color: Brown/Tan | Size: 6

    New With Defects. Store Display Models And Have A Couple Areas Of Discoloration In The Leather - See Pics. Line On Inside Label To Prevent In Store Returns. Size 6 Color: Warm Cinnamon Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores... more

    $74.00

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    Madewell Shoes | Madewell The Benning Chelsea Boot Sz 6 Nn017 | Color: Black | Size: 6

    Madewell Shoes | Madewell The Benning Chelsea Boot Sz 6 Nn017 | Color: Black | Size: 6

    Boots Are New Without Box, Display Item, So The Bottoms Are A Tad Dirty Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On... more

    $80.00

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    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 14 Brown Boot Medium

    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 14 Brown Boot Medium

    *Chelsea boot from Georgia Boot *Wateproof and high-abrasion full-grain Tec-Tuff leather upper *Padded collar and tongue *Elastic gore stretch panels for easy on and off *Mesh lining *Comfort core memory foam insole *Fiberglass shank *Flexible stroble... more

    $159.95

    FREE shipping

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    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 9 Brown Boot Medium

    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 9 Brown Boot Medium

    *Chelsea boot from Georgia Boot *Wateproof and high-abrasion full-grain Tec-Tuff leather upper *Padded collar and tongue *Elastic gore stretch panels for easy on and off *Mesh lining *Comfort core memory foam insole *Fiberglass shank *Flexible stroble... more

    $159.95

    FREE shipping

    go to store
    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 10 Brown Boot Medium

    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 10 Brown Boot Medium

    *Chelsea boot from Georgia Boot *Wateproof and high-abrasion full-grain Tec-Tuff leather upper *Padded collar and tongue *Elastic gore stretch panels for easy on and off *Mesh lining *Comfort core memory foam insole *Fiberglass shank *Flexible stroble... more

    $159.95

    FREE shipping

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    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

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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

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    Matrix Chelsea Boot

    Matrix Chelsea Boot

    Men's AllSaints Matrix Chelsea Boot - Black - Casual boots Premium leather and stretchy elastic goring make this versatile Chelsea boot an optimal choice throughout the year. Pull-on style with elastic gore insets Leather and textile upper/leather... more

    $379.00

    FREE shipping

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    Hogan Chelsea Boot

    Hogan Chelsea Boot

    Men's Vance Co. Hogan Chelsea Boot - Black - Casual boots Slip into the Hogan Chelsea boot by Vance Co for an instantly polished and graceful look. This vegan synthetic boot features stretch gore details to enable easy on/off and a Tru Comfort Foam... more

    $79.99

    FREE shipping

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    Thorpe Chelsea Boot

    Thorpe Chelsea Boot

    Men's Vance Co. Thorpe Chelsea Boot - Blue - Casual boots Experience casual luxury with the Thorpe Chelsea boot from Vance Co. Boasting a pull-on silhouette, this ankle boot has vegan synthetic upper with stretch gore accents and wingtip detailing for... more

    $69.99

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    Hanford Chelsea Boot

    Hanford Chelsea Boot

    Men's Thomas & Vine Hanford Chelsea Boot - Brown - Casual boots Step out in style and comfort with the Hanford Chelsea boot from Thomas & Vince. Dual stretch gores make this pull-on boot flexible and comfortable to wear. A Tru Comfort insole ensures... more

    $99.99

    FREE shipping

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    Thorpe Chelsea Boot

    Thorpe Chelsea Boot

    Men's Vance Co. Thorpe Chelsea Boot - Black - Casual boots Experience casual luxury with the Thorpe Chelsea boot from Vance Co. Boasting a pull-on silhouette, this ankle boot has vegan synthetic upper with stretch gore accents and wingtip detailing for... more

    $69.99

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    Cyrus Chelsea Boot

    Cyrus Chelsea Boot

    Men's Eastland Cyrus Chelsea Boot - Brown - Casual boots Get inspired by the classiness of the Cyrus Chelsea boot by Eastland. Dual gores on the sides of the pull-on boot offer a comfortable fit while the aux leather sole absorbs shocks while keeping... more

    $84.99

    FREE shipping

    go to store
    Cyrus Chelsea Boot

    Cyrus Chelsea Boot

    Men's Eastland Cyrus Chelsea Boot - Brown - Casual boots Get inspired by the classiness of the Cyrus Chelsea boot by Eastland. Dual gores on the sides of the pull-on boot offer a comfortable fit while the aux leather sole absorbs shocks while keeping... more

    $69.99

    go to store
    Hogan Chelsea Boot

    Hogan Chelsea Boot

    Men's Vance Co. Hogan Chelsea Boot - Black - Casual boots Slip into the Hogan Chelsea boot by Vance Co for an instantly polished and graceful look. This vegan synthetic boot features stretch gore details to enable easy on/off and a Tru Comfort Foam... more

    $79.99

    FREE shipping

    go to store
    Thorpe Chelsea Boot

    Thorpe Chelsea Boot

    Men's Vance Co. Thorpe Chelsea Boot - Black - Casual boots Experience casual luxury with the Thorpe Chelsea boot from Vance Co. Boasting a pull-on silhouette, this ankle boot has vegan synthetic upper with stretch gore accents and wingtip detailing for... more

    $69.99

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    Hanford Chelsea Boot

    Hanford Chelsea Boot

    Men's Thomas & Vine Hanford Chelsea Boot - Black - Casual boots Step out in style and comfort with the Hanford Chelsea boot from Thomas & Vince. Dual stretch gores make this pull-on boot flexible and comfortable to wear. A Tru Comfort insole ensures... more

    $99.99

    FREE shipping

    go to store
    Thorpe Chelsea Boot

    Thorpe Chelsea Boot

    Men's Vance Co. Thorpe Chelsea Boot - Black - Casual boots Experience casual luxury with the Thorpe Chelsea boot from Vance Co. Boasting a pull-on silhouette, this ankle boot has vegan synthetic upper with stretch gore accents and wingtip detailing for... more

    $69.99

    go to store
    Hogan Chelsea Boot

    Hogan Chelsea Boot

    Men's Vance Co. Hogan Chelsea Boot - Black - Casual boots Slip into the Hogan Chelsea boot by Vance Co for an instantly polished and graceful look. This vegan synthetic boot features stretch gore details to enable easy on/off and a Tru Comfort Foam... more

    $79.99

    FREE shipping

    go to store
    Hanford Chelsea Boot

    Hanford Chelsea Boot

    Men's Thomas & Vine Hanford Chelsea Boot - Brown - Casual boots Step out in style and comfort with the Hanford Chelsea boot from Thomas & Vince. Dual stretch gores make this pull-on boot flexible and comfortable to wear. A Tru Comfort insole ensures... more

    $99.99

    FREE shipping

    go to store
    Thorpe Chelsea Boot

    Thorpe Chelsea Boot

    Men's Vance Co. Thorpe Chelsea Boot - Gray - Casual boots Experience casual luxury with the Thorpe Chelsea boot from Vance Co. Boasting a pull-on silhouette, this ankle boot has vegan synthetic upper with stretch gore accents and wingtip detailing for... more

    $69.99

    go to store
    Port Chalmers Chelsea Boot

    Port Chalmers Chelsea Boot

    Men's Rodd & Gunn Port Chalmers Chelsea Boot - Brown - Casual boots Stretchy side panels mean easy entry into this versatile and stylish Chelsea boot crafted from burnished European leather. Pull-on style with elastic gore insets Leather and textile... more

    $238.00

    FREE shipping

    go to store
    Thorpe Chelsea Boot

    Thorpe Chelsea Boot

    Men's Vance Co. Thorpe Chelsea Boot - Brown - Casual boots Experience casual luxury with the Thorpe Chelsea boot from Vance Co. Boasting a pull-on silhouette, this ankle boot has vegan synthetic upper with stretch gore accents and wingtip detailing for... more

    $69.99

    go to store
    Madewell Shoes | Https://Www.Madewell.Com/The-Benning-Chelsea-Boot-Nn017.Html | Color: Brown | Size: 9

    Madewell Shoes | Https://Www.Madewell.Com/The-Benning-Chelsea-Boot-Nn017.Html | Color: Brown | Size: 9

    Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. Leather Upper. Leather Lining. Man-Made Sole. Do Well:... more

    $80.00

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    Madewell Shoes | Madewell Wyckoff Chelsea Lugsole Boots In Smoked Graphite | 8 | Color: Gray | Size: 8

    Madewell Shoes | Madewell Wyckoff Chelsea Lugsole Boots In Smoked Graphite | 8 | Color: Gray | Size: 8

    The Wyckoff Chelsea Lugsole Boot Ready For All Your Supercute Fall Fits, These Suede Chelsea Boots Have Stretchy Gores And Wear-Alllday-Everywhere Chunky Lugsoles. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A... Well,... more

    $66.00

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    Madewell Shoes | - Madewell The Wyckoff Chelsea Lugsole Boot Nn020 Worn Once Chocolate Raisin | Color: Brown | Size: Various

    Madewell Shoes | - Madewell The Wyckoff Chelsea Lugsole Boot Nn020 Worn Once Chocolate Raisin | Color: Brown | Size: Various

    Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. When You Select Your... more

    $78.00

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    Madewell Shoes | Madewell $198 The Wyckoff Chelsea Lugsole Boot Leather Size 10.5 Nn020 | Color: Black/Cream | Size: 10.5

    Madewell Shoes | Madewell $198 The Wyckoff Chelsea Lugsole Boot Leather Size 10.5 Nn020 | Color: Black/Cream | Size: 10.5

    Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know.6" Shaft Height1 1/2"... more

    $97.00

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    Madewell Shoes | Madewell Wyckoff Chelsea Lugsole Boot | Color: Black | Size: Various

    Madewell Shoes | Madewell Wyckoff Chelsea Lugsole Boot | Color: Black | Size: Various

    “Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. 1 1/2" Heel Height.... more

    $150.00

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    Madewell Shoes | Madewell $198 The Wyckoff Chelsea Lugsole Boot Black Leather Size 12 Nn020 | Color: Black | Size: 12

    Madewell Shoes | Madewell $198 The Wyckoff Chelsea Lugsole Boot Black Leather Size 12 Nn020 | Color: Black | Size: 12

    Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know.6" Shaft Height1 1/2"... more

    $97.00

    go to store
    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 13 Brown Boot W

    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 13 Brown Boot W

    *Chelsea boot from Georgia Boot *Wateproof and high-abrasion full-grain Tec-Tuff leather upper *Padded collar and tongue *Elastic gore stretch panels for easy on and off *Mesh lining *Comfort core memory foam insole *Fiberglass shank *Flexible stroble... more

    $159.95

    FREE shipping

    go to store
    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 8 Brown Boot Medium

    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 8 Brown Boot Medium

    *Chelsea boot from Georgia Boot *Wateproof and high-abrasion full-grain Tec-Tuff leather upper *Padded collar and tongue *Elastic gore stretch panels for easy on and off *Mesh lining *Comfort core memory foam insole *Fiberglass shank *Flexible stroble... more

    $159.95

    FREE shipping

    go to store
    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 8 Brown Boot W

    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 8 Brown Boot W

    *Chelsea boot from Georgia Boot *Wateproof and high-abrasion full-grain Tec-Tuff leather upper *Padded collar and tongue *Elastic gore stretch panels for easy on and off *Mesh lining *Comfort core memory foam insole *Fiberglass shank *Flexible stroble... more

    $159.95

    FREE shipping

    go to store
    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 12 Brown Boot Medium

    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 12 Brown Boot Medium

    *Chelsea boot from Georgia Boot *Wateproof and high-abrasion full-grain Tec-Tuff leather upper *Padded collar and tongue *Elastic gore stretch panels for easy on and off *Mesh lining *Comfort core memory foam insole *Fiberglass shank *Flexible stroble... more

    $159.95

    FREE shipping

    go to store
    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 10 Brown Boot W

    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 10 Brown Boot W

    *Chelsea boot from Georgia Boot *Wateproof and high-abrasion full-grain Tec-Tuff leather upper *Padded collar and tongue *Elastic gore stretch panels for easy on and off *Mesh lining *Comfort core memory foam insole *Fiberglass shank *Flexible stroble... more

    $159.95

    FREE shipping

    go to store
    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 8.5 Brown Boot W

    Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 8.5 Brown Boot W

    *Chelsea boot from Georgia Boot *Wateproof and high-abrasion full-grain Tec-Tuff leather upper *Padded collar and tongue *Elastic gore stretch panels for easy on and off *Mesh lining *Comfort core memory foam insole *Fiberglass shank *Flexible stroble... more

    $159.95

    FREE shipping

    go to store

    More information about Men's Shoes

    Best prices on Double gore chelsea boot, Stretchable 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.