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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

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

All Terrain Series Water Resistant Chelsea Boot

Men's Blundstone All Terrain Series Water Resistant Chelsea Boot - Brown - Casual boots Dual pull-tabs and stretch side goring mean easy entry into this versatile and hardy Chelsea boot crafted with weather-ready suede. XRD technology in the heel... more

Georgia Boot Athens 360 Waterproof 6in Work Boot - Men's Wide Brown 11 GB00439-110W

Georgia Boot Athens 360 Waterproof 6in Work Boot - Men's Wide Brown 11 GB00439-110W. Built with a 360-degree stitch-out construction this defined heel work boot also features a reinforced toe stitch to prevent sole separation. This waterproof work boot... more

Rocky Boots 1000gr Insulated Hunting Boots w/3M Thinsulate - Men's Mossy Oak Break Up Country 10.5 Wide RKS0309-W-10.5

Rocky Boots 1000gr Insulated Hunting Boots w/3M Thinsulate - Men's Mossy Oak Break Up Country 10.5 Wide RKS0309-W-10.5. The heel brake design of these Rocky Boots provides better grip in low traction conditions. This Rocky Sport Pro Hunting Boot also... more

Georgia Boot Athens 360 Waterproof 6in Work Boot - Men's Medium Brown 11 GB00439-110M

Georgia Boot Athens 360 Waterproof 6in Work Boot - Men's Medium Brown 11 GB00439-110M. Built with a 360-degree stitch-out construction this defined heel work boot also features a reinforced toe stitch to prevent sole separation. This waterproof work... more

Oswald Chelsea Boot

Men's Thomas & Vine Oswald Chelsea Boot - Black - Casual boots Look fascinating in the Thomas & Vine Oswald Chelsea boot. Suede accent at the heel beautifully contrasts the premium leather upper of this pull-on boot that's supported on an Extralight... more

Oswald Chelsea Boot

Men's Thomas & Vine Oswald Chelsea Boot - Brown - Casual boots Look fascinating in the Thomas & Vine Oswald Chelsea boot. Suede accent at the heel beautifully contrasts the premium leather upper of this pull-on boot that's supported on an Extralight... more

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

Muck Boots Chore Mid Wateproof Rubber Work Boot - Men's Black 9 CHM-000A-BL-090

Muck Boots Chore Mid Wateproof Rubber Work Boot - Men's Black 9 CHM-000A-BL-090. Perfect for wider calves this waterproof boot is triple-reinforced in the toe and quadruple reinforced in the heel for ultimate durability while built-in Airmesh lining... more

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

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

Muck Boots Chore Mid Wateproof Rubber Work Boot - Men's Black 12 CHM-000A-BL-120

Muck Boots Chore Mid Wateproof Rubber Work Boot - Men's Black 12 CHM-000A-BL-120. Perfect for wider calves this waterproof boot is triple-reinforced in the toe and quadruple reinforced in the heel for ultimate durability while built-in Airmesh lining... more

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

Madewell Shoes | Madewell The Bradley Chelsea Lugsole Boots - Size: 7.5 | Color: Black | Size: 7.5

New Without Tags - No Call-Outs Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert 6" Shaft Height (Based On Size 7). 1 1/2" Heel Height. Leather... more

Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boot-Size 6.5 | Color: Brown | Size: 6.5

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 Height. 1 1/2" Heel Height. Leather Upper. Leather... more

Rocky Boots 1000gr Insulated Hunting Boots w/3M Thinsulate - Men's Mossy Oak Break Up Country 9 Medium RKS0309-M-9

Rocky Boots 1000gr Insulated Hunting Boots w/3M Thinsulate - Men's Mossy Oak Break Up Country 9 Medium RKS0309-M-9. The heel brake design of these Rocky Boots provides better grip in low traction conditions. This Rocky Sport Pro Hunting Boot also... more

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

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

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

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

Rocky Boots 1000gr Insulated Hunting Boots w/3M Thinsulate - Men's Mossy Oak Break Up Country 9 Wide RKS0309-W-9

Rocky Boots 1000gr Insulated Hunting Boots w/3M Thinsulate - Men's Mossy Oak Break Up Country 9 Wide RKS0309-W-9. The heel brake design of these Rocky Boots provides better grip in low traction conditions. This Rocky Sport Pro Hunting Boot also... more

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

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

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

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

Watson Chelsea Boot

Men's Thomas & Vine Watson Chelsea Boot - Brown - Casual boots Take the classic route to your suave styling with the Thomas & Vine Watson Chelsea boot. The wingtip toe with brogue detailing provides a timeless look, while the memory foam insole ensures... more

Leather Chelsea Formal Boots

Men's Dolce & Gabbana Leather Chelsea Formal Boots - Brown - Casual boots 100% authentic Dolce & Gabbana Mens Chelsea formal boots Brown leather exterior Leather outer sole Stretch bands on the sides for easy entry and exit Zipper closure Logo details... more

Farsley Chelsea Boot

Men's Barbour Farsley Chelsea Boot - Brown - Casual boots Stretchy side panels mean easy entry into this dapper Chelsea boot equipped with dual pull-tabs and a breathable cotton-blend lining. more

Patina Chelsea Boot

Men's Mezlan Patina Chelsea Boot - Black - Casual boots A side zipper and stretch goring lend easy wear to a sophisticated Chelsea boot rendered in smooth leather for styling versatility. Leather and textile upper and lining/rubber and leather sole... more

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

Corbin Chelsea Boot

Men's Thomas & Vine Corbin Chelsea Boot - Black - Casual boots Give your attire a polished update with the Corbin Chelsea boot from Thomas & Vine. This high-top profile is made from leather and comes with side goring panels for a precise fit and... more

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

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

Marshon Chelsea Boot

Men's Vance Co. Marshon Chelsea Boot - Brown - Casual boots Look handsome in the Vance Co Marshon Chelsea boot. Elastic stretch panels offer a flexible fit, while the 6mm Tru Comfort Foam insole offers supreme comfort. Vegan leather upper. Slip-on.... more

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

Corbin Chelsea Boot

Men's Thomas & Vine Corbin Chelsea Boot - Brown - Casual boots Give your attire a polished update with the Corbin Chelsea boot from Thomas & Vine. This high-top profile is made from leather and comes with side goring panels for a precise fit and... more

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