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    Best Seller
    Tory Burch Shoes | $520 Tory Burch Expedition Chelsea Boot Chunky Square Toe Black 8 (Me10) | Color: Black | Size: 8

    Tory Burch Shoes | $520 Tory Burch Expedition Chelsea Boot Chunky Square Toe Black 8 (Me10) | Color: Black | Size: 8

    Floor Model And Tried On Excellent Back Tabs Are Missing - Please See Pictures!! Size Info True To Size. Details & Care A Rubber Toe Caps Off This Expedition-Seeking Leather Boot Crafted With Stretchy Side Goring And Balanced On A Block Heel For Steady... more

    $270.00

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    Free People Shoes | Free People White James Chunky Chelsea Boots 40 | Color: White | Size: 10

    Free People Shoes | Free People White James Chunky Chelsea Boots 40 | Color: White | Size: 10

    Nib Free People James Chelsea Ankle Boots Side Zip Closure Stretch Side Panels For Easy On Cushion Footbed Color Is White But Looks More Like A Cream Color Leather Uppers 6” Shaft Height 3.5” Chunky Heel 1” Platform more

    $85.00

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    Best Seller
    Zara Shoes | Hp Zara Trafaluc Chunky Chelsea Boots | Color: Black | Size: 6

    Zara Shoes | Hp Zara Trafaluc Chunky Chelsea Boots | Color: Black | Size: 6

    Zara Trafaluc Chunky Chelsea Boots. Seem Like Leather But Actual Material Not Listed. Worn But Definitely Have A Ton Of Life Left In Them! Stretch Sides, Pull- On. Super Comfortable. Some Mild To Moderate Creasing/ Scratching/ Denting (Mostly From... more

    $40.00

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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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    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

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    Tigran Chelsea Boot

    Tigran Chelsea Boot

    Men's Stacy Adams Tigran Chelsea Boot - Brown - Casual boots When it comes to looking cool and fashionable, you definitely have to go with the Stacy Adams Tigran Chelsea boot. Made using suede, this slip-on boot is detailed with modern welt that... more

    $59.99 $44.98

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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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    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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    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

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    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 10

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 10

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

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    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 14

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 14

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

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    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 8.5

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 8.5

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

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    Coach Shoes | Coach Black Leather Boot Giana Stretch Bootie Slip On Chunky Heel Y2k | Color: Black | Size: 9b

    Coach Shoes | Coach Black Leather Boot Giana Stretch Bootie Slip On Chunky Heel Y2k | Color: Black | Size: 9b

    **Excellent Condition With Minimal Wear And Very Few Scuff Marks Which Are Not Very Noticeable. Please View Pictures For Reference Leather Upper Leather Lining And Footbed Leather Outsole Pull On 3 1/2" Heel Open To Reasonable Offers more

    $43.00

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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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    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

    $25.00

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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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    Madewell Shoes | Madewell Size 9.5 Wyckoff Chelsea Lugsole Boots In Chocolate Raisin | Color: Brown | Size: 9.5

    Madewell Shoes | Madewell Size 9.5 Wyckoff Chelsea Lugsole Boots In Chocolate Raisin | Color: Brown | Size: 9.5

    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. When You Select Your... more

    $130.00

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    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boot Sz 10 Nn020 | Color: Black | Size: 10

    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boot Sz 10 Nn020 | Color: Black | Size: 10

    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

    $89.00

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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 Chocolate Leather Size 11 Nn020 | Color: Brown | Size: 11

    Madewell Shoes | Madewell $198 The Wyckoff Chelsea Lugsole Boot Chocolate Leather Size 11 Nn020 | Color: Brown | Size: 11

    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

    $87.00

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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

    $87.00

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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

    $87.00

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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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    Tigran Chelsea Boot

    Tigran Chelsea Boot

    Men's Stacy Adams Tigran Chelsea Boot - Black - Casual boots When it comes to looking cool and fashionable, you definitely have to go with the Stacy Adams Tigran Chelsea boot. Made using suede, this slip-on boot is detailed with modern welt that... more

    $59.99 $44.98

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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

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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

    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

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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 8.5 Brown Boot Medium

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 8.5 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

    FREE shipping

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

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 12 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

    FREE shipping

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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 11 Brown Boot W

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 11 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 10.5 Brown Boot Medium

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 10.5 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

    FREE shipping

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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 11 Brown Boot Medium

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 11 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

    FREE shipping

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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 9.5 Brown Boot Medium

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 9.5 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

    FREE shipping

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

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 9 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

    FREE shipping

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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 10.5 Brown Boot W

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 10.5 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 11.5 Brown Boot W

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 11.5 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 Medium

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 8 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

    FREE shipping

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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 10 Brown Boot W

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 10 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 10 Brown Boot Medium

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 10 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

    FREE shipping

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    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 11.5 Brown Boot Medium

    Georgia Boot 6" DuraBlend Sport Waterproof Chelsea - Mens 11.5 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

    FREE shipping

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    More information about Men's Shoes

    Best prices on Chunky slip on chelsea 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.