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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 - Brown - Casual boots 100% Suede, 100% Rubber. Made in Italy. more | $587.78 $479.63 FREE shipping go to store |
| Best Seller  | Men's Tod's Slip-on Chelsea Ankle Boots - Brown - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 1.5cm 100% Calf Leather, 100% Rubber. Made in Italy. more | $694.65 $566.83 FREE shipping 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 |
 | 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 |
 | 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 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 |
 | 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 |
 | Men's Ann Demeulemeester Stef Chelsea Ankle Boots - Black - Casual boots Synonymous with timeless elegance, the Chelsea boot gets a low-key update from Ann Demeulemeester. A menswear classic, they will go with a navy or grey suit, or with jeans and a... more | $796.18 $489.17 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 |
 | Burgundy Sprayed Leather Chelsea Boots Men's Acne Burgundy Sprayed Leather Chelsea Boots - Brown - Casual boots Ankle-high buffed leather boots in burgundy. more | $1,050.00 $452.00 FREE shipping 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 |
 | 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 |
 | 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 |
 | Madewell Size 8.5 The Carlin Shearling Chelsea Boot Ankle Boot Suede Rugged Made Of Water-Resistant Suede With A Rugged Lug Sole, These Pull-On Chelsea Boots Are Fully Lined In Real Shearling To Up The Cozy Factor. Basically: All-Weather Boots You'll... 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 |
 | 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 |
 | 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 |
 | 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 |
 | Madewell Walker Chelsea Suede Ankle Boot - Size 9 Retail Price $$188.00 + Tax In Supersoft Suede, These Sleek Chelsea Boots Give A Low-Key Nod To Timeless '60s Styles. The Not-Too-High Heel Is Made For Adventuring Day Or Night. 2" Heel. Suede Upper.... 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 |
 | J. Crew Shoes | J Crew Olive Green Pull On Chelsea Rain Boot Ankle 7 | Color: Green | Size: 7 J Crew Olive Green Pull On Chelsea Rain Boot Ankle 7 Preowned Has Some Wear See Photos Shoe3 more | go to store |
 | Free People Shoes | Free People Atlas Black Puffer Chelsea Ankle Boots | Color: Black | Size: 8.5 Please Read Description Above About This Brand New Puffer Boot! more | go to store |
 | Free People Atlas Chelsea Black Leather Suede Ankle Boots Minimalist Grunge Size 40 Gently Used more | go to store |
 | Madewell Shoes | Madewell Sonia Ankle Low Chelsea Boots Leather | Color: Brown/Tan | Size: Various Madewell Sonia Ankle Low Chelsea Boots Brand New In Box Retail $188 Color: Tan And Black With Snakeskin Pattern / "Heather Natural Multi" Description: An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A... more | go to store |
 | Coach Suffolk Patchwork Black Leather Chelsea/Ankle Boots, Snakeskin, Calf, 6.5b Euc 1.25” Heel more | go to store |
 | Madewell Shoes | Guc Madewell Chelsea Ankle Boots Size 9 | Color: Black | Size: 9 Super Versatile - Block Heel Style Black Some Signs Of Wear - See Pics And Ask Questions Before Purchasing more | go to store |
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