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| Best Seller  | Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Womens Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... more | go to store |
 | Men's Tod's Chelsea Ankle Boots - Black - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 2cm 100% Calf Leather, 100% Rubber. Made in Italy. more | $694.65 $566.83 FREE shipping go to store |
| Best Seller  | Men's Tod's Chelsea Ankle Boots - Brown - Casual boots 100% Suede, 100% Rubber. Made in Italy. more | $587.78 $479.63 FREE shipping go to store |
 | Men's Tod's Chelsea Ankle Boots - Black - Casual boots Dimensions: Heel: 4cm, Height: 14cm, Sole: 2.5cm 100% Leather, 100% Rubber, 72% Polyester, 28% Elastane. Made in Italy. more | $662.59 $572.48 FREE shipping go to store |
 | Reposhing This Item I Purchased From @Cooldudz. Used 1x For A Wedding Rehearsal And Now That I Am Working From Home I Don’t Wear/Need Heels Anymore. Loved Them, Fit Well And Very Stylish. more | go to store |
 | J. Crew Gray Leather Chelsea Ankle Boot. Made In Italy With 2 Inch Heel, Ankle Strap And Gold Hardware. 03868 Color: Gray Size: Women's 8 more | go to store |
 | 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 |
 | J. Crew Shoes | J. Crew Leather Chelsea Boots Pull On Ankle Boot | Color: Black | Size: 10 J. Crew Leather Chelsea Boots Pull On Ankle Boot Black Smooth Buttery Leather Size 10 In Great Condition! Finish Your Fall Look In The Smooth Leather J.Crew Chelsea Lexi Boot Featuring A Breathable Leather Lining And Lightly Cushioned, Stationed Insole... more | go to store |
 | Men's Tricker's Henry Ankle Chelsea Boot - Black - Casual boots 100% Leather. Made in Italy. more | $732.05 $597.36 FREE shipping go to store |
 | Henry Country Ankle Chelsea Boot Men's Tricker's Henry Country Ankle Chelsea Boot - Brown - Casual boots 100% Leather. Made in Italy. more | $732.05 $597.36 FREE shipping go to store |
 | Burgundy Ankle Strap Chelsea Boots Women's Toga Burgundy Ankle Strap Chelsea Boots - Black - Ankle boots Ankle-high buffed calfskin Chelsea boots in burgundy. Signature hardware throughout. more | $605.00 $315.00 FREE shipping go to store |
 | Men's Moncler Larue Chelsea Ankle Boots - Blue - Casual boots Larue Chelsea ankle boots in leather. Round toe Elasticated side panels Rear pull tab Rear logo ring Embossed logo at midsole Debossed logo at heel cap. 100% Leather. more | FREE shipping 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 |
 | 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 Black Boot Size 9 Bootie Ankle Boots Wear To Toes- Scuffing. Rubbing. Minor Scratching At Heels. Gently Used. Good Condition. Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toeand Cut... 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 |
 | Madewell Size 8 The Ivy Croc Embossed Leather Chelsea Boots Ankle Boots In Brown Platform Utilitarian Lug Soles In Excellent Almost Like New Condition. Very Clean Inside & Out. Tags: Classic Chunky Lug Soles Neutral Versatile Business Casual Office... 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 |
 | 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 Size 9 Brynn Ankle Heeled Chelsea Boot With Velvet Trim 1 1/2” Heel 4 1/2” Shaft Height Leather, Suede Upper Man-Made Sole Style # Mb834 Slight Scuffing On Rim Of Front Toes But Not Noticeable When Wearing more | go to store |
 | Black Leather Upper Chelsea Side Panels Ankle Height Really Great Condition Gently Worn 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 Shoes | Bnib Madewell Sonia Snakeskin Chelsea Ankle Boots 6 | Color: Black/Tan | Size: 6 Python Snake Print Heather Natural Leather Chelsea Booties With Almond Toe And Stacked Wooden Heel, Comes With Box 1.75'' Heel 3'' Shaft Pull-On With Elastic Gore Insets Tapered, Stacked Heel Cushioned Footbed Leather Upper Leather Lining 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 |
 | Reach New Heights In A Pair Where Elevated Neutrals And A Wedge Heel Take Center Stage. In Great Preowned Condition. Minor Wear To The Outer Sole. One Mark At The Inner Side Gore Panel Of The Left Boot. See Photos. Suede Leather Upper Leather Lining... more | go to store |
 | This Is A Fabulous Pair Of Authentic Gucci Flores Calfskin Horsebit Chain Ankle Boots Size 38.5 In Black. These Boots Are Mid Length On The Leg And Crafted Of Soft Black Lambskin Leather. These Boots Feature A 1.5 Inch Heel, A Gold Horsebit, Silver... more | go to store |
 | Stud Details And A Smart Cap Toe Kick This Chelsea Boot Up A Notch. *** No Box! Leather Upper With Shiny Cap Toe And Heel Pull-On Styling With Elastic Side Panels Lightly Cushioned Footbed 1-1/2" Heel Height The Last Picture Is A Stock Photo. Eu Size... more | go to store |
 | Anthropologie Shoes | Anthropologie Chelsea Ankle Boots | Color: Pink | Size: 10 Pre-Owned. Good Condition. No Box. Please See All Pictures As These Are The Exact Shoes You Will Receive. **There Is Some Stains/Scuffs On The Toe Fronts. See Last Picture. Womens Size 10 Usps Shipping. Same Day Or Next Day Shipping. Please Follow As... 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 |
 | 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 |
 | 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 |
 | New Without Box more | go to store |
 | Madewell Bryce Suede Chelsea Ankle Boot Equestrian Brown Size 10 New Without Tag Shoe Is Store Return And May Have Minor Blemish more | go to store |
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