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| 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 |
 | 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 |
| 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 |
 | ® 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 |
 | ® 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 Suede/waterproof Boots|dress Shoes Men's Ugg ® Burleigh Chelsea Suede/waterproof Boots|dress Shoes - Brown - 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 suede upper,... more | FREE shipping 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 |
 | Free People Tan Leather Ankle Boots Made In Spain Size 38/8 Euc No Box more | go to store |
 | Jessica Simpson Boots |Jessica Simpson Brown Booties|Jessica Simpson Ankle Boots | Brown Heeled Boots | Brown Leather Ankle Boots | Western Boots | Boho Ankle Boots | Distressed Boots Size 6.5 Women’s Zip Up Side I Am Not Sure If These Are Leather, But... 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 |
 | Complement Your Classic Look With The New Keith Suede Chelsea Boot From Levi’s! These Handsome Chelsea Boots Feature Soft Suede Uppers With Dual Elastic Gore For Easy On And Off And Memory Foam Footbed For Lasting Comfort. 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 |
 | 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 |
 | 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 |
 | Beautiful Boots 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 |
 | Madewell Shoes | Madewell Ainsley Chelsea Ankle Boots Size 6 | Color: Black/Brown | Size: 6 Reposhing This Item I Purchased From @Jjfrommycircle. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! 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 |
 | Excellent Condition. Appear To Have Been Worn Once Or Twice. Great Pair Of Clog Ankle Boots By Madewell. See Photos And Feel Free To Ask Questions. more | go to store |
 | Farylrobin Womens Grey Suede Leather Pointy Toe Chelsea Ankle Bootie Size: Us 6 With Slate Suede And Chelsea Styling, This Is The Perfect Fall Bootie. Condition: Excellent Pre-Owned Condition See Pictures For Details Worn Once Sole: Rubber Sole With... more | go to store |
 | Stylish And Chic. Beautiful Details. Polished Leather. Made In Italy. Condition: Pre-Owned. Very Great Condition. May Have Minor Scuffs, Spots And Creases Due To The Delicate Nature Of The Leather. No Shoe Box. No Shoe Dust Bag. Thanks For Sharing The... more | go to store |
 | Anthropologie Shoes | Hoss Intropia - Tan Suede Ankle Chelsea Boots, 9 | Color: Brown/Tan | Size: 9 Hoss Intropia Tan Suede Ankle Boots With Back Zip Detail And Stacked Wooden Heel Pre-Owned - Fair Condition, Denim Dye Spot Transfers At The Edges On Top, Can Be Professionally Cleaned For Additional Cost, Added Vibram Sole, See Images, Ask Questions,... more | go to store |
 | Madewell - Regan Cognac Brown Ankle Chelsea Boots - 7.5 Women's 100% Genuine Leather And Super Comfortable 2.5 Inch Heel Almond Toe Rich Cognac Brown Color Western Cowboy Style more | go to store |
 | Free People Shoes | Free People Atlas Suede Chelsea Ankle Boot | Color: Brown | Size: Various Details: Nwob Pieced Leopard Printed Leather Pull-On Bootie Elasticized Insets Scalloped Trim And Stud Details Cushioned Footbed 5 1/2" Shaft more | go to store |
 | Soft Light Tan Leather Booties Buckle Strap And Adjustable Closure 3” Sturdy Heel Little Leather Bows On The Back Heel With The Kate Spade Logo Super Cute And Versatile Good Condition, Some Light Water Marks See All Photos For Condition I Ship Quickly... more | go to store |
 | Madewell Shoes | Brand New Madewell Chelsea Ankle Boots | Color: Brown | Size: 7.5 Brand New Madewell Pull-On Ankle Chelsea Boots Never Worn. Brand New With Original Tag And Shoe Box. Classical Ankle Chelsea Boots In Size 7.5. Color Is Dark Cabernet. 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 |
 | Free People Shoes | Free People Castillo Chelsea Boots Ankle Size 37 | Color: Brown | Size: 37 Free People Castillo Chelsea Boots Ankle Size 37 Flaw: Upper Wrinkles For Regular Use Scratches Please Note: The Item You See Is The Exact Item You Are Receiving. This Item Is Used, Therefore The Pictures Show The Best Description Of The Condition Of... more | go to store |
 | Euc Minimal Wear On The Shoes. Got Dust During Storage. Needs A Suede Brush To Clear Up. more | go to store |
 | Excellent Gently Used Condition As Pictured With Minor Overall Wear. Size Womens 11. In The Versatile Coach Bowery Beadchain Bootie, A Suede Leather Top Is Accented With Dazzling Beadchain Trim And Ribbed Ankle Gores For Easy On-And-Off Use. Suede... more | go to store |
 | Coach Shoes | Coach Bowery Chelsea Ankle Boot In Burgundy | Color: Brown/Red | Size: 5 The Bowery Chelsea Boot From Coach Takes A Classic Silhouette And Updates It With Modern Appeal. This Ankle Bootie Features A Sleek Almond Toe And Ombre Block Heel For An Eye-Catching Finish. Details: * Runs Large, Fits Like Size 6 * Suede Upper *... more | go to store |
 | Anthropologie Size 7.5 Brown Suede Metallic Chelsea Ankle Booties Boots. Great Pre-Owned Condition more | go to store |
 | Note: Shoes Are Different Sizes, Left Shoe Is 37.5, Right Shoe Is 38.5 New Free People Atlas Chelsea Leather Puffer Upper Ankle Boots Black Size 7.5 - 8.5 Featuring All-Over Stud Detailing And Brogued And Scalloped Trims For An Eye-Catching Look, The... more | go to store |
 | Madewell Shoes | Madewell Spencer Chelsea Ankle Boot Black Size 9 | Color: Black/Tan | Size: 9 New Questions? Leave A Comment Below! 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 Sherpa Lined Suede Chelsea Ankle Boots 7.5 | Color: Tan | Size: 7.5 New Without Box Size 7.5 more | go to store |
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