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| Best Seller  | 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 go to store |
 | 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 | FREE shipping go to store |
| Best Seller  | 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 | FREE shipping go to store |
 | 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 | go to store |
 | 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 | FREE shipping go to store |
 | 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 go to store |
 | 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 | go to store |
 | 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 | go to store |
 | Madewell Shoes | Madewell The Ainsley Chelsea Boot J8295 Leather | Color: Black | Size: Various Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: We've Added An Extra Layer Of Padding To Make Them Even Easier On The Feet. Logo On Sole Marked To Prevent Retail Store... more | go to store |
 | Georgia Boot Tough Beyond Dispute Chelsea EH WP - Mens 9.5 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 | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | Michael Kors Miller Chelsea Boot Brown 10 The Miller boot will add instant polish to denim and the season’s flirty dresses alike. Designed in a timeless silhouette, this stylish pair features stretch side panels and a back pull tab for ease of wear. The slight heel and all-around platform add... more | $255.00 $69.00 go to store |
 | Michael Kors Miller Chelsea Boot Brown 6.5 The Miller boot will add instant polish to denim and the season’s flirty dresses alike. Designed in a timeless silhouette, this stylish pair features stretch side panels and a back pull tab for ease of wear. The slight heel and all-around platform add... more | $255.00 $69.00 go to store |
 | Territory Boots Territory Holloway Cap Toe Chelsea Boot - Brown - 11.5 Upgrade your wardrobe with the Holloway boot by Territory. This uniquely designed chelsea boot features a round-toe and genuine leather uppers with a two-tone cuff detail at the heel. A 12 mm Tru Comfort Foamâ„¢ Footbed adds cushion to your every step,... more | go to store |
 | 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 | go to store |
 | 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 | go to store |
 | 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 | FREE shipping go to store |
 | Washington Grand Laser Chelsea Boot Men's Cole Haan Washington Grand Laser Chelsea Boot - Brown - Casual boots Look sharp in this polished leather Chelsea boot detailed with laser-cut perforations at the toe. Lightweight cushioning and a moisture-wicking lining mean all-day comfort and... more | FREE shipping go to store |
 | 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 | go to store |
 | Men's Mephisto Murray Zip Chelsea Boot - Black - Casual boots A stretchy mesh inset and handy side zip flank the shaft of a streamlined leather boot resting on a comfortable cushion of shock-absorbing Soft-Air technology. Cushioned footbed with arch... more | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | 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 | go to store |
 | 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 | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | 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 go to store |
 | 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 | go to store |
 | 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 | FREE shipping go to store |
 | 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 | go to store |
 | 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 | go to store |
 | 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 | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | Terence Waterproof Chelsea Boot Men's Geox Terence Waterproof Chelsea Boot - Black - Casual boots An elegant buckle bridges the stretchy inset of this waterproof Chelsea Boot crafted from smooth leather. This boot is made with the brand's patented tech sole, which is durable,... more | $210.00 $168.00 FREE shipping go to store |
 | Men's AllSaints Steam Chelsea Boot - Black - Casual boots Stretchy goring and a rubber sole enhance the ease and comfort of a leather chelsea boot that adds a polished and refined look to any ensemble. Leather upper and lining/rubber and leather sole... more | $299.00 $224.25 FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | 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 | $1,455.53 $740.57 FREE shipping go to store |
 | 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 | go to store |
 | 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 | go to store |
 | 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 | FREE shipping go to store |
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