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    WIDE FIT Darcy Chelsea Boot - black

    WIDE FIT Darcy Chelsea Boot - black

    Elevate your look with the Darcy Chelsea Boot. Perfect for AM to PM, enjoy the stylish detailing and ultra comfortable cushioned insoles. Key Features Include:- Rounded toe ankle boot- Wide width fit- Side zip closure- Cloudwalkers cushioned insole-... more

    $99.99 $69.99

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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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    Best Seller
    Free People Shoes | Black Free People Ankle Chelsea Boot | Color: Black | Size: 8

    Free People Shoes | Black Free People Ankle Chelsea Boot | Color: Black | Size: 8

    There Are A Euro Size 41 (Us 8) Free People Cowboy/ Chelsea Boot Style Stretchy On The Side Like A Chelsea Boot Small Heel more

    $45.00

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    Free People Shoes | Free People Atlas Ankle Studded Suede Chelsea Boots Black 9.5 | Color: Black | Size: 39.5eu

    Free People Shoes | Free People Atlas Ankle Studded Suede Chelsea Boots Black 9.5 | Color: Black | Size: 39.5eu

    Brand - Free People Size - Eu 39.5 / Us 9.5 Excellent Preowned Condition Ankle, Chelsea, Studded Trim, Scalloped Lace Trim, Pull On, Side Stretch, Suede, Leather, Round Toe, Comfortable, Hiking, Causal, Winter, Fall, Combat, Booties more

    $85.00

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    Holloway Chelsea Boot

    Holloway Chelsea Boot

    Men's Territory Holloway Chelsea Boot - Black - Casual boots A unique take on a traditional profile, the Holloway Chelsea boot by Territory is sure to catch the onlooker's attention. Elastic stretch panels at the ankle offer a comfortable slip-on... more

    $79.99

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    Holloway Chelsea Boot

    Holloway Chelsea Boot

    Men's Territory Holloway Chelsea Boot - Brown - Casual boots A unique take on a traditional profile, the Holloway Chelsea boot by Territory is sure to catch the onlooker's attention. Elastic stretch panels at the ankle offer a comfortable slip-on... more

    $79.99

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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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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 13 Brown Boot Medium

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 13 Brown Boot Medium

    *Work boot from Georgia Boot *Full-grain leather upper *3D knit stretch collar *Stretch gusset *Pull-on fit *DuraBlend midsole provides excellent rebound and comfort *Fiberglass shank *Heat/chemical/abrasion and slip-resisting Carbo-Tec outsole *1-1/2"... more

    $154.95

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    WIDE FIT Darcy Chelsea Boot - black

    WIDE FIT Darcy Chelsea Boot - black

    Elevate your look with the Darcy Chelsea Boot. Perfect for AM to PM, enjoy the stylish detailing and ultra comfortable cushioned insoles. Key Features Include:- Rounded toe ankle boot- Wide width fit- Side zip closure- Cloudwalkers cushioned insole-... more

    $99.99 $69.99

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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 7.5 Brown Boot Medium

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 7.5 Brown Boot Medium

    *Work boot from Georgia Boot *Full-grain leather upper *3D knit stretch collar *Stretch gusset *Pull-on fit *DuraBlend midsole provides excellent rebound and comfort *Fiberglass shank *Heat/chemical/abrasion and slip-resisting Carbo-Tec outsole *1-1/2"... more

    $154.95

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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 12 Brown Boot W

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 12 Brown Boot W

    *Work boot from Georgia Boot *Full-grain leather upper *3D knit stretch collar *Stretch gusset *Pull-on fit *DuraBlend midsole provides excellent rebound and comfort *Fiberglass shank *Heat/chemical/abrasion and slip-resisting Carbo-Tec outsole *1-1/2"... more

    $154.95

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    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

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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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    Madewell Shoes | - Madewell Chelsea Tan Slip On Ankle Boots Sz 9 | Color: Tan | Size: 9

    Madewell Shoes | - Madewell Chelsea Tan Slip On Ankle Boots Sz 9 | Color: Tan | Size: 9

    Tan Leather With Elastic Stretch On Both Side For Easy Slip On Round Toe Leather Sole Preowned But In Good Condition more

    $65.00

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    J. Crew Shoes | J Crew Chelsea Ankle Boot In Evergreen Size 5 | Color: Green | Size: 5

    J. Crew Shoes | J Crew Chelsea Ankle Boot In Evergreen Size 5 | Color: Green | Size: 5

    Slightly Worn J Crew Ankle Boot. True To Size. Rubber With Elastic Stretch Around Ankle. Low Heel. more

    $20.00

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    Anthropologie Shoes | Anthropologie Sixtyseven Distressed Croc Leather Boho Chelsea Ankle Boots | Color: Black | Size: 37eu

    Anthropologie Shoes | Anthropologie Sixtyseven Distressed Croc Leather Boho Chelsea Ankle Boots | Color: Black | Size: 37eu

    Great Used Condition. Distressed Croc Chelsea Ankle Boots By Anthropologie Brand Sixtyseven In Black. Chic, Edgy Aesthetic, A Versatile Capsule Wardrobe Piece For The Season That Can Be Dressed Up Or Worn Casually. Slip-On Ankle Boots With Textured... more

    $50.00

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    Madewell Shoes | Madewell Nico Gray Suede Pull-On Chelsea Ankle Boots Size 9 | Color: Gray | Size: 9

    Madewell Shoes | Madewell Nico Gray Suede Pull-On Chelsea Ankle Boots Size 9 | Color: Gray | Size: 9

    Madewell Nico Gray Suede Pull-On Chelsea Ankle Boots Size 9 Pointed Toe Very Small Heeled Sole, Less Than 1" Pull On Style Stretch Panel For Ease Getting On And Off Great Condition, A Few Tiny Marks As Shown more

    $100.00

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    Free People Shoes | Free People Chelsea Textile Atlas Boots Blue Kilm Western Ankle Scallop 40 | Color: Blue | Size: 40eu

    Free People Shoes | Free People Chelsea Textile Atlas Boots Blue Kilm Western Ankle Scallop 40 | Color: Blue | Size: 40eu

    Excellent Condition ... No Flaws!! Bundle And Save 20%... Free Shipping On All Bundles! ~ Offers Welcome! ~ Fast Shipping! ~ For Offers European Size 40 Appreciate Your Wonderful Sense Of Style And Make A Statement In These Jaw-Dropping Chelsea Boots... more

    $98.00

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    Zara Shoes | Euc Zara Chunky Chelsea Combat Black High Ankle Boot Size 39 (8.5) | Color: Black | Size: 8.5

    Zara Shoes | Euc Zara Chunky Chelsea Combat Black High Ankle Boot Size 39 (8.5) | Color: Black | Size: 8.5

    Excellent Used Condition. Size 39. Ankle Upper Is Stretchy On The Sides. more

    $40.00

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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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    Ventura Chelsea Boot

    Ventura Chelsea Boot

    Men's Thomas & Vine Ventura Chelsea Boot - Brown - Casual boots Make a charismatic entry in the Thomas & Vine Ventura Chelsea boot. A plush suede shaft gives a different dimension to the ankle boot, crafted with a genuine leather upper. An Extralight... more

    $99.99

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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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    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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    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

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    Ventura Chelsea Boot

    Ventura Chelsea Boot

    Men's Thomas & Vine Ventura Chelsea Boot - Black - Casual boots Make a charismatic entry in the Thomas & Vine Ventura Chelsea boot. A plush suede shaft gives a different dimension to the ankle boot, crafted with a genuine leather upper. An Extralight... more

    $99.99

    FREE shipping

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    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

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    Free People Shoes | Free People Brooks Lug Sole Chelsea Boots | Color: Cream | Size: 10

    Free People Shoes | Free People Brooks Lug Sole Chelsea Boots | Color: Cream | Size: 10

    A Contemporary Spin On The Classic Chelsea Style, These Timeless Ankle-Covering Boots Feature A Chunky Sole For An Exaggerated Look. A Neutral Boot To Pop Any Outfit Fp Collection Color Chalk Artisan Crafted From Fine Leathers And Premium Materials, Fp... more

    $21.00

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    Free People Shoes | Free People Brooks Lug Sole Chelsea Boot | Color: Black | Size: 8

    Free People Shoes | Free People Brooks Lug Sole Chelsea Boot | Color: Black | Size: 8

    Free People Brooks Lug Sole Chelsea Boot In Good Pre Owned Condition. Some Parts Can Use A Brushing As Can Be Expected With Suede. Some Very Minimal Creasing On Ankle Part. Please See All Pictures For Wear. Minor Wear On Soles. Features A Super-Chunky... more

    $105.00

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    J. Crew Shoes | J. Crew Willa Stacked Heel Leather Chelsea Boots, Black, 9 | Color: Black | Size: 9

    J. Crew Shoes | J. Crew Willa Stacked Heel Leather Chelsea Boots, Black, 9 | Color: Black | Size: 9

    These Refined Leather Ankle Boots Have A High Shaft That Looks Extra-Cool Peeking Out From The Hem Of A Midi Skirt Or Your Favorite Straight- Leg Jeans. Detail We Love: Stretchy Side Panels Make Them Easier To Take On And Off. Leather Upper And Lining.... more

    $95.00

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    Free People Shoes | Free People Nwt Arlo Santa Fe Chelsea Boot Croc Embossed Leather Cognac Brown | Color: Brown | Size: 8

    Free People Shoes | Free People Nwt Arlo Santa Fe Chelsea Boot Croc Embossed Leather Cognac Brown | Color: Brown | Size: 8

    Free People Nwt Arlo Santa Fe Chelsea Boot Croc Embossed Leather Cognac Brown Size 8 Nwt From Marshall’s Cognac Brown Caramel Embossed Leather Upper Croc Back Zipper Closure Approx 1.5” Heel Stretchy Top Half Mixed Media Ankle Length more

    $100.00

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    Anthropologie Shoes | Cecelia New York Chelsea Boots - Black | Color: Black | Size: 8

    Anthropologie Shoes | Cecelia New York Chelsea Boots - Black | Color: Black | Size: 8

    New In Box, Anthropologie, Cecelia Black Chelsea Boots. Pull On Styling (Stretch Goring Side Panels) Suede Upper Leather Insole Eva Sole & Heel 2¼" Heel 1" Platform more

    $175.00

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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 $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

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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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    Gucci Shoes | Gucci Ankle Boots | Color: Black | Size: 8

    Gucci Shoes | Gucci Ankle Boots | Color: Black | Size: 8

    Vintage Black Gucci Ankle Boots. Leather Lining, Stretchy Fabric Exterior, 2.5” Heel, Size 38c, In Excellent Condition, Priced To Sell! more

    $275.00

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    Madewell Shoes | Madewell Gwenda Platform Ankle Boot In Black Leather | Color: Black | Size: 8

    Madewell Shoes | Madewell Gwenda Platform Ankle Boot In Black Leather | Color: Black | Size: 8

    Worn 2 Times With Stretch Gores, A Chunky Platform And Stacked Heel, These Leather Ankle Boots Are The Best Of Both Worldscomfy And Cool. Plus, Our Mwl Cloudlift Lite Padding Makes It Feel Like You're Walking On A...Well, You Know. more

    $118.00

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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 9 Brown Boot W

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 9 Brown Boot W

    *Work boot from Georgia Boot *Full-grain leather upper *3D knit stretch collar *Stretch gusset *Pull-on fit *DuraBlend midsole provides excellent rebound and comfort *Fiberglass shank *Heat/chemical/abrasion and slip-resisting Carbo-Tec outsole *1-1/2"... more

    $154.95

    FREE shipping

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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 13 Brown Boot W

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 13 Brown Boot W

    *Work boot from Georgia Boot *Full-grain leather upper *3D knit stretch collar *Stretch gusset *Pull-on fit *DuraBlend midsole provides excellent rebound and comfort *Fiberglass shank *Heat/chemical/abrasion and slip-resisting Carbo-Tec outsole *1-1/2"... more

    $154.95

    FREE shipping

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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 8 Brown Boot W

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 8 Brown Boot W

    *Work boot from Georgia Boot *Full-grain leather upper *3D knit stretch collar *Stretch gusset *Pull-on fit *DuraBlend midsole provides excellent rebound and comfort *Fiberglass shank *Heat/chemical/abrasion and slip-resisting Carbo-Tec outsole *1-1/2"... more

    $154.95

    FREE shipping

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    More information about Men's Shoes

    Best prices on Two toned chelsea ankle boots, 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.