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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  | 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 |
 | Men's Bronx Drew Shoe by Drew in Grey Leather (Size 10 1/2 M) This Drew® mens classic lace-up ankle boot offers a timeless style tailored perfectly to compliment any attire. The Bronx by Drew features added depth with a removable footbed and ultimate arch build-up. Premium quality leather and lightweight, shock... more | go to store |
 | Men's Bronx Drew Shoe by Drew in Grey Leather (Size 13 M) This Drew® mens classic lace-up ankle boot offers a timeless style tailored perfectly to compliment any attire. The Bronx by Drew features added depth with a removable footbed and ultimate arch build-up. Premium quality leather and lightweight, shock... more | go to store |
 | Men's Bronx Drew Shoe by Drew in Grey Leather (Size 10 M) This Drew® mens classic lace-up ankle boot offers a timeless style tailored perfectly to compliment any attire. The Bronx by Drew features added depth with a removable footbed and ultimate arch build-up. Premium quality leather and lightweight, shock... more | go to store |
 | Free People Tan Leather Ankle Boots Made In Spain Size 38/8 Euc No Box more | go to store |
 | Madewell The Bohnam Chelsea Boot Ankle Boots Booties Black Western Size 8.5. Leather Boots, Pointed Toe, Wood 2” Block Heel. more | go to store |
 | 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 |
 | Men's Bronx Drew Shoe by Drew in Grey Leather (Size 8 M) This Drew® mens classic lace-up ankle boot offers a timeless style tailored perfectly to compliment any attire. The Bronx by Drew features added depth with a removable footbed and ultimate arch build-up. Premium quality leather and lightweight, shock... more | go to store |
 | Men's Bronx Drew Shoe by Drew in Brown Leather (Size 9 1/2 M) This Drew® mens classic lace-up ankle boot offers a timeless style tailored perfectly to compliment any attire. The Bronx by Drew features added depth with a removable footbed and ultimate arch build-up. Premium quality leather and lightweight, shock... more | go to store |
 | Men's Bronx Drew Shoe by Drew in Grey Leather (Size 14 M) This Drew® mens classic lace-up ankle boot offers a timeless style tailored perfectly to compliment any attire. The Bronx by Drew features added depth with a removable footbed and ultimate arch build-up. Premium quality leather and lightweight, shock... more | go to store |
 | Men's Bronx Drew Shoe by Drew in Brown Leather (Size 13 M) This Drew® mens classic lace-up ankle boot offers a timeless style tailored perfectly to compliment any attire. The Bronx by Drew features added depth with a removable footbed and ultimate arch build-up. Premium quality leather and lightweight, shock... more | go to store |
 | Reposhing Only Because I Ordered The Wrong Size. Not Sure What I Was Thinking. These Are A 9. (I’m An 8) They Are In Perfect Condition. Questions? Leave A Comment Below! 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 |
 | J. Crew Shoes | Black Chelsea Ankle Boots 6.5 | Color: Black | Size: 6.5 These Are Black Chelsea Ankle Boots That I Wore So Religiously That I Bought Two Pairs When They Were On Sale As Back Up. I Don’t Need Two Extra Pairs Tho So I’m Selling These Now. Have Hardly Been Worn But Were In Storage For A While And They Deserve... more | go to store |
 | Coach Brand Black Leather Ankle Chelsea-Style Boots. It Seems The "Coach Style" Of This Shoe Is Maybe Called "Reine." - Made In Italy - 9.5 Size (I'm A Size 10 And Fit Comfortably, Just Becomes A Little Snug With Inserts. I Believe A 9, 9.5, Or 10... 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 |
 | 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 |
 | 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 |
 | Rare Find! Free People Castillo Chelsea Boots Ankle | Size 37 (6-6.5) Made In Portugal With Real Patent Leather And Meant To Look Distressed. Wooden Sole And Chunky Metal Accents. Slight Creases Near Toes But Not Not Effect The Functionality Of The... more | go to store |
 | J. Crew Shoes | J. Crew Chelsea Leather Ankle Boot, Size 9 | Color: Black | Size: 9 These Are In Great Condition Although They Are Used. I Did Not Find Any Scuffs Except A Few On The Heel - Please See The Last Picture. Leather. Size 9. Black. more | go to store |
 | Madewell Ainsley Brown Leather Chelsea Ankle Boots Size 6.5 Gently Used, Signs Of Wear Are On The Sole. Leather Is In Great Condition. more | go to store |
 | These Are Stylish, Comfortable, And Timeless Chelsea Boots From Free People. They Are Crafted From High Quality Genuine Leather That's Slightly Aged And Distressed. Gorgeous Dark Red/Burgundy/Oxblood Color. - Elastic Side Panels For An Easy Pull-On... more | go to store |
 | Tory Burch Shoes | New.....Tory Burch Chelsea Black Ankle Boot...Size 10 | Color: Black | Size: 10 Classic Chelsea Boot Defined By Elasticated Sides And A Back Pull Tab Features A Refined Profile With A Pointed Toe. Crafted In Smooth Calf Leather With A Buffed Leather Sole.Read Less 1.77" Heel Shaft Height: 17.3cm Calf Leather Upper; Elastic Trim... more | go to store |
 | Free People Atlas Chelsea Black Leather Suede Ankle Boots Minimalist Grunge Size 40 Gently Used more | go to store |
 | Madewell Leather Chelsea Boots Embossed Snake Size 6 Excellent Used Condition, No Major Flaws Slip On Style Low Ankle Height Short Block Heel Slightly Pointed Toe Leather Upper/Lining/Sock Synthetic Sole more | go to store |
 | Questions? Leave A Comment Below! more | go to store |
 | Madewell Sonia Low Chelsea Boot, Size 6.5 In Heather Natural Multi. $188 #0320x1.1.9 - Low Chelsea Boot - Snakeskin Embossed Leather - Almond Toe - 1.75" Stacked Block Heel - 3" Shaft - Cushioned Footbed - Leather Upper And Lining more | go to store |
 | Coach Shoes | Coach Chelsea Leather Ankle Boot | Color: Green | Size: 10 Leather Upper Man-Made Leather Lining And Footbed Leather Outsole Pull On Side Gore In Darker Green Nwot. Box Not Included. Smells Of Leather. No Flaws. Fast Shipping. 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 Cognac Brown Leather Chelsea Boots With Stretch Panels For Easy Pull-On. Tag Size 8. Fits 7.5-8 In My Opinion. Style Eo824 Preowned. Shows Signs Of Wear Including Scuffs On Toes, Wear On Back Heels, Wear On Bottoms Of Soles, Creasing In Midfoot... more | go to store |
 | New With Box Free People James Tan Brown Leather Chunky James Chelsea Ankle Boots Inside Zippers, Chunky, Apx 3.5" Heel, 1" Platform Size 41 more | go to store |
 | Euc Kate Spade Bellamy Ankle Booties Stone - Light Grey , Mauve Undertone Gold Hardware Size 9.5 Leather Rubber Sole Shaft Measures Approximately 4.5" From Arch Heel Measures Approximately 1" Platform Measures Approximately 0.25 Boot Opening Measures... more | go to store |
 | Free People Atlas Chelsea Bootie Black Leather Fabric 40 New Without Box Tufts Of Faux Shearling Woven Into A Jacquard Pattern Create Eye-Catching Texture On This Mixed-Media Version Of A Classic Chelsea Boot. Studded Patchwork Look 5 1/2" Shaft... more | go to store |
 | Brand - Free People Size - Eu 39.5 / Us 9.5 Excellent Preowned Condition Ankle, Chelsea, Studded Trim, Scalloped Lace Trim, Pull On, Side Stretch, Suede, Leather, Round Toe, Comfortable, Hiking, Causal, Winter, Fall, Combat, Booties more | go to store |
 | Coach Snake Skin And Leather Patchwork Chelsea Ankle Boots Size: 8.5 Black Good Used Condition-Flaws Include Some Scrapes Of Normal Wear And Some Fading On The Suede Otherwise In Good Condition Tags: Fall, Autumn, Western Boots, Boots more | go to store |
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