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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 |
 | 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 |
| Best Seller  | 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 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 |
 | Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Black | Size: 6 Size 6 No Box Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. When You Select Your Size, "H"... more | go to store |
 | Madewell Shoes | Madewell The Benning Chelsea Boot Sz 7 Nn017 | Color: Black | Size: 7 New Without Box And A Defect There’s A Small Hole In The Elastic By The Seam In The Right Shoe See Pics Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. And, Cushiness Alert: Our Mwl Cloudlift Lite... more | 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 |
 | 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 |
 | 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 | FREE shipping go to store |
 | Territory Boots Territory Holloway Cap Toe Chelsea Boot - Grey - 10.5 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 Holloway Cap Toe Chelsea Boot - Brown - 8 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 Chelsea Boot - Brown - 11.5 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 Golden Goose Deluxe Brand John Chelsea Boots - Natural - Casual boots Revisiting a timeless shape under a disruptive and distressed light: our John Chelsea Boots redefine the concept of classic. This model features a caramel-colored suede upper... more | FREE shipping 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 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 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 |
 | Yellowstone Chelsea Hiking Boot Men's Territory Yellowstone Chelsea Hiking Boot - Black - Casual boots When the hills beckon, just lace-up the Territory Yellowstone Chelsea hiking boot and get going with confidence. The water-resistant boot has dual elastic stretch panels that offer... more | FREE shipping go to store |
 | Men's Golden Goose Deluxe Brand ’S Chelsea Boots - Black - Casual boots A timeless silhouette: the Chelsea boot, featuring clean simple lines, is the perfect blend of style and comfort. This men’s model features a black leather upper and gold-colored... 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 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 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 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 |
 | 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 Ainsley Chelsea Boot In Metallic | Color: Gold | Size: 7 Like New Madwell Ainsley Chelsea Boot Gently Worn - Minor Scuffing Crafted From Metallic 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... more | go to store |
 | 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 | go to store |
 | Low Chelsea Boots From Madewell. Heather Natural Color Snake-Embossed Leather Boot - Stretch On Sides With A Perfect Pointed Toe. Western Look. New Never Worn Outside. No Box Madewell Heather Natural Size 7 #Western #Southwestern #Work #Party #Snake more | go to store |
 | Madewell Shoes | Madewell 6.5 Ainsley Brown Leather Chelsea Boots | Color: Brown | Size: 6.5 Madewell 6.5 Ainsley Brown Leather Chelsea Boots. Used, Good Conditionsee Pictures, Plenty Of Life Left. Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: Our Mwl... more | go to store |
 | 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 | go to store |
 | 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 | go to store |
 | 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 | go to store |
 | J. Crew Shoes | J. Crew Pull-On Chelsea Suede Boots In Desert Sand | Color: Black/Tan | Size: 9 J. Crew Pull-On Chelsea Suede Boots In Desert Sand Feature A Leather Lining, Soft Suede With A Stretchy Side Panel, Just Pull 'Em On And Go! You'll Want To Reach For Our Easy Oh-So-Walkable Chelsea Boots Everyday. Item Does Not Include The Original Box. more | go to store |
 | Madewell Shoes | Madewell The Ainsley Chelsea Boot In Black Size 8.5 | Color: Black | Size: 8.5 Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Please Note: The Manufacturer Comments That These Boots Fit Narrow But Will Stretch With Wear Recommending Going Up A Size If You Have A... more | go to store |
 | Listing As Pre-Owned. Excellent Condition. Line On Inside Label To Prevent In Store Returns. Color: True Black Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. And, Cushiness Alert: Our Mwl Cloudlift Lite... more | go to store |
 | Madewell Shoes | Madewell Ainsley Chelsea Boot - Size 7.5 | Color: Black | Size: 7.5 Madewell Leather Ankle Boots Gently Worn Elastic Stretch On Interior And Exterior Side Ankle Minor Scuffing On Left Shoe Shown In Photo more | go to store |
 | 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 | go to store |
 | 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 | go to store |
 | Coach Shoes | Coach Elijah Chelsea Boots | Color: Red | Size: 8 Coach Elijah Chelsea Boots In Good Used Condition. Has Creases From Normal Wear. Polished Calf Leather Gives This Tomboyish Boot A Rich Sheen, While The Saddle-Colored Stripe On The Sole Is A Nod To Heritage Coach(Tm) Craftsmanship. Fashion Meets... more | go to store |
 | Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Brown/Tan | Size: 7 Moving Soon So I Really Need To Clear Out The Closet! Gently Worn Madewell Boots In Cognac Color. Totally Love These Boots But I Am Never Reaching For Them These Days. From Madewell: Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared... more | go to store |
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