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| Best Seller  | Madewell ‘The Grayson’ Chelsea Boot Black Leather Pointed Toe Ankle Booties Size: 10 Color: Black & Brown Style: J8293 Condition: Preloved Condition (Normal Signs Of Wear; Small Flaws To Leather Noted; Creasing At Toe Noted; Please See/Zoom In To All... more | go to store |
 | Details Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side Zipper Closure Cushioned... more | go to store |
| Best Seller  | Brand: Free People Style: James Chelsea Boots Heeled Ankle Booties Color: White Material: Leather With Rubber Gum Sole Size: Eu 40, Fits Like A 9 Has A Slightly Narrow Fit In My Opinion, Though I Do Better With Wider Fit Shoes Condition: New, No Box.... more | go to store |
 | ® Hillmont Chelsea Leather Cold Weather Boots|dress Shoes Men's Ugg ® Hillmont Chelsea Leather Cold Weather Boots|dress Shoes - Brown - Casual boots Sleek and functional, our take on a traditional chelsea silhouette incorporates seam-sealed waterproof leather for enhanced protection from the elements. Even... more | $190.00 $132.99 go to store |
 | ® Burleigh Chelsea Leather/waterproof Boots|dress Shoes Men's Ugg ® Burleigh Chelsea Leather/waterproof Boots|dress Shoes - Black - Casual boots The Burleigh Chelsea offers the fashionable presence of a sneaker with the functionality and sleek profile of a Chelsea boot. With a waterproof leather upper,... more | FREE shipping go to store |
 | ® Skyview Chelsea Leather Boots|dress Shoes Men's Ugg ® Skyview Chelsea Leather Boots|dress Shoes - Black - Casual boots Constructed from water-resistant leather and enhanced with sealed seams, the Skyview emerges as an ageless chelsea boot tailored for winter and subsequent seasons. Its... more | $160.00 $111.99 go to store |
 | Men Boots Comfortable Fashion Breathable Lace Up Solid Color Outdoor Autumn Winter Wide Calf Leather Boot Description: Gender: Men Boy Upper Material:Artificial leather Sole Material: Rubber Scenes:Indoor&Outdoor Fashion Leisure Style:Comfortable... more | $51.24 $45.96 go to store |
 | Mens Shoes High Top Elastic Band Sport Shoes Fashion Casual Shoes Mens Plus Size Ankle Boots Slip on Boots for Men Gender: Men boy Upper Material:Artificial leather Sole Material: Rubber Scenes: Indoor&Outdoor Fashion Leisure Style: Princess Casual Toe... more | $45.07 $40.43 go to store |
 | Details Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side Zipper Closure Cushioned... more | go to store |
 | Free People Tan Leather Ankle Boots Made In Spain Size 38/8 Euc No Box more | go to store |
 | Nwt Free People Back Loop Ankle Boot Currently Sold Out On Asos For $178 Washed Black Size 38/ Us 8 New With Box! Made From Distressed Leather. Distressing Is Intentional. So Cool Ankle Boots Featured In A Pull-On Style And Distressed Leather With An... more | go to store |
 | Coach Boots Mens 10.5 Brown Leather Chukka Boots Shoes Ankle Boots. Flaw: Leather Peeling On The Inside Please See Pictures. On The Outside No Flaws. Questions? Leave A Comment Below! more | go to store |
 | Lonesome Fringe Ankle Boot By Free People. Suede Ankle Boot With Foldover Top And Fringe Trimming. Leather Wrapped Chord Detailing Around The Ankle. Leather Tab Detailing At Each Bottom Side And Back Low Stacked Heel. Gently Worn With Only 2 Marks As... more | go to store |
 | Brand New, Never Worn. These Were Too Big For Me. I Usually Wear 5-5.5 Depending On Brand. I Wish They Fit Because They Are Super Cute And Great Quality. I Love The Color. Perfect For Light And Dark Outfits. Comment With Questions! more | go to store |
 | Free People Shoes | Free People Atlas Puffer Chelsea Ankle Boots New | Color: Black | Size: 8.5 Nwob, No Flaws! Free People Atlas Chelsea Puffer Boot, Black These Adorable Boots Sold Out Instantly Everywhere! Multiple Sizes Avail Gleaming Studs And Scalloped Edges Contrast Against The Puffy Profile Of A So-Cool Chelsea Boot Crafted From Leather.... more | go to store |
 | Excellent Preowned Condition Crafted From Hand-Finished Leather, These Sleek Chelsea Boots Offer A Cushioned Insole And A Sturdy Heel For Comfortable, Outfit-Elevating Style. Due To The Nature Of Hand-Finished Leather, Expect Slight Variation In Color... more | go to store |
 | Free People Shoes | Free People Brooks Chelsea Ankle Boots | Color: Green | Size: 6.5 Leather Upper Ankle-High Chelsea Boot Shaft Zipper Closure Lightly Cushioned Footbed Lug Outsole Pull-On New Without Box Size 36.5 (6.5) more | go to store |
 | Reposhing This Item I Purchased From @Pinetreeposh. Loved It, But They Are Too Small I’m Usually A 9 Or 9.5. These Fit So Snug, I Would Compare Them To An 8, Maybe An 8.5. more | go to store |
 | Gucci Shoes | Gucci Worsh Black Leather Chelsea Ankle Boots | Color: Black | Size: 11 Only Wore Once To Big It Comes With Original Box And Dust Bags As Well In Great Condition No Scratches Or Marks more | go to store |
 | Anthropologie Ankle Boots - Leather Upper And Lining - Pull-On Style - Stacked Heels - Taupe/Tan - Size 9 Gently Pre-Owned; Some Light Scrapes To Heels As Shown. more | go to store |
 | Good Preowned Condition. Light Wear As Shown In Photos. An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. Pull-On Style With Elastic Gore Insets Cushioned Footbed... more | go to store |
 | Madewell Spencer Taupe Chelsea Slip On Leather Ankle Boots Slip On Stacked Block Heel Chelsea Style Ankle Length Western Leather Upper And Lining Taupe Color Size: 8.5 Condition: Good, Has Some Scuffing more | go to store |
 | Bran New In A Box. Size 7.5 But They Run 1 Size Bigger =8.5. Genuine Embossed Croc Leather. Black Elastic Sides, Pointy Toe. Curved Hills 1.75” more | go to store |
 | Designer: Gucci Size: Marked As 11 / Us 11.5 (Conversion Per Designer's Website) Condition: Authentic And Brand New Style Name / Number: 624661 Cdzk0 1000 Material: Leather Upper, Leather Unique Features: Classic Black Leather Mens Chelsea Ankle Boots.... more | go to store |
 | Free People Brooks Lug Sole Chelsea Boot Tall Ankle Leather Shoes Black Suede Size 38/Us 8 Nwob New Without Box. Store Display Model. Minor Wear From Being Tried On In A Retail Environment. Please See Photos. Never Worn Outside. Smoke Free Home. Fast... more | go to store |
 | Free People Atlas Chelsea Ankle Boot Eu 40 In My Opinion, They Fit Like 9.5 Us Good Used Condition Minor Signs Of Wear, Wear On Bottom, Light Scuff On Side Pictured. Free People Logo Worn Off On Inside And Some Glitter Inside I Couldn't Get Out Brass... more | go to store |
 | Excellent Used Conditions Worn Once No Notable Scuffs Or Flaws Elevate Your Style With These Stunning Coach Suffolk Patchwork Black Leather Chelsea/Ankle Boots. These Boots Feature A Unique Patchwork Design And A Sleek Black Color That Complements Any... more | go to store |
 | Gucci Marmont Double G Mateless Leather Chelsea Ankle Boots Size 40.5 Black Leather Matelasse Leather Double G 2 Inches Made In Italy Comes With Original Box, Tags, Dust Bags, Booklets more | go to store |
 | Madewell Shoes | Madewell Bryce Suede Leather Chelsea Ankle Boots Tan Size 7 | Color: Tan | Size: 7 Madewell Bryce Suede Leather Chelsea Ankle Boots Tan Size 7 Small Stacked Heel, Pull Tabs, Elasticized Panels, And An Almond Toe. Gently Used With Normal Wear. Small Spot On The Left Boot Toward The Opening On The Front. Most Wear Is On The Bottom... more | go to store |
 | Some Wear But In Good Condition. more | go to store |
 | Reposhing This Item I Purchased From @Pnwposhboss. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! more | go to store |
 | Designer: Gucci Condition: Authentic And Brand New Style Name / Number: 643619 Dtnb0 1063 Material: Leather Upper, Rubber Sole Unique Features: Black Leather Mens Chelsea Ankle Boots. Crafted From Leather, This Pair Features Elastic Side Panels, Pull... more | go to store |
 | Free People Shoes | Free People Atlas Puffer Chelsea Ankle Boots New | Color: Black | Size: Various Nwob, No Flaws! Free People Atlas Chelsea Puffer Boot, Black These Adorable Boots Sold Out Instantly Everywhere! Multiple Sizes Avail Gleaming Studs And Scalloped Edges Contrast Against The Puffy Profile Of A So-Cool Chelsea Boot Crafted From Leather.... more | go to store |
 | 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 | go to store |
 | Kate Spade Shoes | Kate Spade New York Ankle Chelsea Boots | Color: Black | Size: 10 Kate Spade New York Ankle Chelsea Boots Black & Metallic Leather & Rubber Trim Round-Toes With Glitter Accents Heels: 1.5" Size: 10 In Good Condition, Small Spots On Boots Where Glitter Is Scratched From Being In Closet. - You Can See By The Soles... more | go to store |
 | Michael Kors Shaw Flat Suede Bootie Ankle Boots Chelsea Tan Camel Size 9 A Sharply Bootie Fashioned From Smooth ,Burnished Black Leather Dials Up The Chic Appeal Of Your Daily Style, While Logo-Etched Hardware Flashes At The Heel For A Signature... more | go to store |
 | J. Crew Black Leather Slip-On Style Ankle Booties With Elastic Panels For Easy On/Off. Modern Pointed Toe With A Small Block Heel. Tag Size 9 Preowned. Some Wear On Heel Block And Some Minor Creasing Of Leather. Toe Leather Is Nicked And Markings On... more | go to store |
 | Reposhing This Item I Purchased From @Desertsunstyle. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! more | go to store |
 | New Without Box (Has Tags) Multiple Sizes Available Free People Beau Western Ankle Chelsea Boot Embossed Gold Leather Embossed Reptile Genuine Leather Chelsea Western Style Gold Metallic Block Heel 1.5" Pointed Toe Made In India. Elastic Side Gussets.... more | go to store |
 | Free People James Leather Chelsea Ankle Boots White Size 41 Equivalent To Us 11 Side Zip Elasticized Inset Cushioned Footbed 6" Shaft Height 3.5" Inch Chunky Heel With 1" Platform New In Box more | go to store |
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