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| Best Seller  | Madewell Sonia Leather Snakeskin Chelsea Boots. Size 7.5 Light Wear Ships Without Original Shoe Box. more | go to store |
 | Step Up Your Shoe Game With These Stylish Chelsea Ankle Boots By Madewell. Crafted With Black Leather, These Boots Feature A Round Toe Shape And A Pull-On Closure For Easy Wear. The Mid-Height Stacked Block Heel Provides Comfort And Style, Making Them... more | go to store |
| Best Seller  | Kate Spade Sedgewick Domina Leopard Print Chelsea Ankle Rain Boots. Product Details Material Rubber With Elastic And Rubber Heel Features 1.2" Heel Pull On Back Tab Water-Resistant Size Is A Ladies 6/7 Eu 37 Great Preowned Condition With Only Some... more | go to store |
 | Free People James Black Leather Chelsea Heeled Ankle Boot Nwot Sz 41 Make Me An Offer! Special Discounts Available For Bundles Of 2 Items Or More! Questions? Leave A Comment Below! more | go to store |
 | In Excellent Preowned Condition Madewell Boots. Size 8. Platform Chelsea Boot. Pull-On Style With Elastic Gore Insets. Classic Round Toe Silhouette. Pull Tab In Back For Easy On And Off Access. Leather And Textile Upper. Leather And Textile Insole.... 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 |
 | Euc Minimal Wear On The Shoes. Got Dust During Storage. Needs A Suede Brush To Clear Up. 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 Vegan Chelsea Gray Ankle Boots | Color: Gray | Size: 8 Size 8 Block Heel In Good Condition more | go to store |
 | American Eagle Outfitters Shoes | Brown Chelsea Ankle Boots | Color: Brown | Size: 6 Brown Chelsea Booties Size 6 From American Eagle Tiny Signs Of Wear On The Heels But Good Condition Still!! more | go to store |
 | J. Crew Shoes | J Crew Chelsea Boot Ankle Brown Size 10 | Color: Brown | Size: 10 J Crew Chelsea Brown Leather Booties Size 10. It Is Comfortable. Soft Leather Pet/Smoke Free Home. Please See Pictures For More Details. more | go to store |
 | J. Crew Shoes | Black Madewell Chunky Chelsea Ankle Boot. Size 8.5. | Color: Black | Size: 8.5 Black Madewell Chunky Chelsea Ankle Boot. Size 8.5. Never Worn. New In Box. more | go to store |
 | Michael Kors Leather Sole Chelsea Ankle Boots 8m Brown Pull On Chunky Heel Very Good Used Condition - Wear On Soles And Light Wear At Top Edge Of Elastic Sections (See Pictures) more | go to store |
 | Madewell Shoes | Madewell Carina Ankle Chelsea Boot In English Saddle Size 6 | Color: Tan | Size: 6 Madewell Carina Ankle Chelsea Boot In English Saddle Woman's Size 6 With A Rounded Toe And Stacked Heel That's Perfect For Walking Around In All Day, This Chelsea Boot Is A Wear-Everywhere Style Standby. Preowned Good Condition. Please See Pictures For... more | go to store |
 | Kate Spade Shoes | Kate Spade Leah Leopard Print Chelsea Ankle Boots | Color: Brown/Tan | Size: 8.5 - Condition 7.5/10, Minimal Wear, Main Flaw Is Rubbing On Front Of Toe, (Not Too Noticeable, Look At Photos For Flaws) - Kate Spade Leah Calf Hair Leopard Print Ankle Boots, Features Chelsea / Stretch Panels On The Side, A Block Heal, Kate Spade Emblem... more | go to store |
 | Nwot Free People Essential Chelsea Ankle Boot Deep River Teal Leather * Size: Eu Size 38 (Us Size 7.5 Per Free People) * Color: Deep River (Teal Green/Blue) * Faded Leather Uppers * Back Zipper Closure * Elastic Side Gore Panels * Cushioned Insoles *... more | go to store |
 | Madewell Bryce Chelsea Camel Brown Suede Ankle Booties Boots Size 8.5 Good Preowned Condition Streamlined And Undeniably Cool, This Suede Chelsea Boot Has A A Low-Key Western Vibe We Love. Cuff Up Or Tuck In Your Jeansthese Hit Right At The Ankle. -... 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 |
 | Chelsea Rain Royal Blue Boots Pull On Rubber Elastic Side Size: 7 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 |
 | Reposhing This Item I Purchased From @Jgsgmma. Loved It, Just Need A Half Size Smaller! 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 |
 | Kate Spade Shoes | Mocha Chelsea Ankle Boots | Color: Brown | Size: 8 Kate Spade Mocha Chelsea Boots. Size 8. Excellent Condition more | go to store |
 | Madewell The Ryan Black Chelsea Leather Pull On Ankle Boots In Size 8.5. In Good Preowned Condition With Some Scuffs And Wear As Shown. Bin Hg3 more | go to store |
 | Madewell Black Chelsea Rain Waterproof Ankle Boots Size 7 Smoke Free Home Bundle For A Discount more | go to store |
 | Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toeand Cut Them Low On The Ankle To Make Your Legs Look Even Longer. A Pull-On Style For In-Between Weather (Just Add Cropped Jeans). Cushiness Alert: We've Added An... 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 |
 | Coach Mens Chelsea Boots Ankle Suede Pull-On Round Toe Leather Insole Brown 8.5d Pull On Round Toe Features A Comfortable Crepe Sole Ribbed Ankle Gores Pull Tab For On-And-Off Ease. Style No. G2290 Suede Upper Leather Lining And Footbed Rubber Outsole... more | go to store |
 | Pre-Owned, Good Gently Used Condition Some Marks Madewell Bryce Suede Boots Heeled Ankle Boots Chelsea Camel Brown Chestnut Tan Size 7 Genuine Suede 2.5" Heel Offers Always Welcome Bundle Items To Save! Sorry No Trades Or Holds more | go to store |
 | Madewell Shoes | Madewell Nico Gray Suede Pull-On Chelsea Ankle Boots Size 9 | Color: Gray | Size: 9 Madewell Nico Gray Suede Pull-On Chelsea Ankle Boots Size 9 Pointed Toe Very Small Heeled Sole, Less Than 1" Pull On Style Stretch Panel For Ease Getting On And Off Great Condition, A Few Tiny Marks As Shown more | go to store |
 | Free People Shoes | Free People Atlas Suede Chelsea Ankle Boot Sz 36/Us 6 | Color: Brown | Size: 6 Free People Atlas Suede Chelsea Ankle Boot Sz 36/Us 6 Pieced Leopard Printed Leather Pull-On Bootie Elasticized Insets Scalloped Trim And Stud Details Cushioned Footbed 5 1/2" Shaft Leather Upper/Lining. Manmade Outsole. New Without Box, Never Worn,... more | go to store |
 | In Good Shape Size 39 more | go to store |
 | Free People James Chelsea Lug Sole Chunky Ankle Boots In Bone White Size 9 Pre-Owned (No Box) Only Worn Once Or Twice But Has Some Scuffs, Tried To Show In Pictures. more | go to store |
 | Free People Shoes | Free People Chelsea Ankle Boot Size 9 | Color: Brown/Green | Size: 9 Free People Chelsea Boot With Green Ankle Detail And Brass Grommets On The Back. Size 9 From A Pet Free And Smoke Free Home. more | go to store |
 | Kate Spade Anew York Magenta Pink Suede Ankle Boots With Block Chunky Heel. Very Nice Used Condition. Slip On Boot With Ribbing On The Side. These Are Super Cute. Size 8.5 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 |
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