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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 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 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 |
 | Kate Spade Shoes | Kate Spade Chelsea Rain Boot | Color: Black/Gold | Size: 8 Excellent Condition, Very Gently Used Rain Boot By Kate Spade. These Are Black And Gold With Cute Spade/Bow On Back. Minimal Wear To Soles. I Just Never Worn Them. Stretch Side For Easy On And Off. more | go to store |
 | Madewell Shoes | Madewell The Ainsley Chelsea Boot | Color: Black | Size: 7.5 Love These Boots, But Only Wore Twice - They’re Too Narrow For My Feet In This Size.* Both Casual And Stylish Leather Booties, With Cloudlift Lite Padding. *They Run Narrow, But Will Stretch With Wear. Go Up A Size If You Have A Wider Foot Or Want To... 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 |
 | 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 |
 | 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 | FREE shipping go to store |
 | 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 | 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 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 | go to store |
 | 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 | go to store |
 | Territory Boots Territory Yellowstone Water Resistant Chelsea Boot - Grey - 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 | 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 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 Vagabond Cameron Chelsea Boot - Black - Casual boots Side stretch panels and a rear pull-tab offer easy wear on a nubuck leather Chelsea boot grounded by a durable lug sole. 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 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 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 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 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 | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | 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 | FREE shipping go to store |
 | 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 | 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 - 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 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 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 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 | FREE shipping 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 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 | FREE shipping go to store |
 | 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 | FREE shipping go to store |
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