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| Best Seller  | Rue Leather Chelsea Ankle Boots Women's Vince Rue Leather Chelsea Ankle Boots - Brown Vince "Rue" Chelsea boots in smooth leather 1.00 in / 25 mm flat heel Boot shaft, approx. more | FREE shipping go to store |
 | Women's Gianvito Rossi Round-toe Ankle Chelsea Boots - Black - Ankle boots Dimensions: Heel: 5cm, Height: 17.5cm, Sole: 3.5cm 100% Calf Leather, 100% Fabric, 100% Rubber. Made in Italy. more | $1,229.00 $707.90 FREE shipping go to store |
| Best Seller  | 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 $473.88 FREE shipping go to store |
 | Women's Ganni Chelsea Leather Ankle Boots - Black Chunky leather Chelsea boots from GANNI featuring black, calf leather, ankle-length, almond toe, elasticated side panels, double pull-tab at the opening, chunky rubber sole and branded insole.... more | FREE shipping go to store |
 | Madewell Tan And Brown Genuine Leather Snake Print Chelsea Ankle Booties. New With Box. Retail Is $198. True To Size. Heel Height Is 1.5" more | go to store |
 | Authentic Gucci Leather Ankle Boots- Lifford Matelasse Chelsea Boot Black Size 40 / 10 I Wore Them Once They Are Too Large For Me My Daughter And I Got Matching Ones For Xmas Gathering Posted Hers For Sale As Well In A Size 37/ 7 Black Napa Leather... more | go to store |
 | Madewell Boots Women’s Size 9.5 Reagan Black Leather Heeled Ankle Boots Booties J8307. Pre-Owned Great Condition. Please See Photos For Description. Thanks! more | go to store |
 | Style : Traditional Classic Boho Leather Minimalist Modern Contemporary Business Casual Office Professional Color : Black Leather Condition : New With Tags Still In The Original Brand Box Packaging Nwt Sized By The Brand: Women's Size 8 Style Name By... more | go to store |
 | Introducing The Stylish And Versatile Madewell The Clog Boot Womens Size 6.5 Black Leather Chelsea Ankle Boots! Crafted From High-Quality Black Leather, These Ankle Boots Feature A Wooden Platform With A Mid-Height Block Heel Of 2-2.9 Inches. The... more | go to store |
 | J Crew Chelsea Boots Black Leather Ankle Boots Nwt Womens Size 7.5 Bt277 New With Box. Msrp $225 Black Leather Pull On Chelsea Boots. Almond Shape Toe And Flat Sole With A Slide Block Heel. Great Shoe For Many Occasions And Can Style With Most Outfits.... more | go to store |
 | J Crew Chelsea Boot Black Suede Nwt Flat Ankle Boot Size 6.5 Pointed Toe New With Box. Msrp $178 Black Suede Chelsea Boots. Pointed Toe Flat Boots With Zipper Closure. Style Name: Flat Ankle Boots Style Number Bt276 Easy To Pair With Any Outfit. Keep... more | go to store |
 | J. Crew Shoes | J. Crew Ankle Boots Chelsea Matte Rain Boots | Color: Blue | Size: 9 J.Crew Chelsea Matte Rain Boots /Size 9 / Color Navy Blue / Has Scuff Marks / more | go to store |
 | J Crew Women’s Rain Boot Size 10 more | go to store |
 | Authentic Gucci Leather Ankle Boots- Lifford Matelasse Chelsea Boot Black Size 37 / 7 Worn Once Flawless Black Napa Leather Slip On Style Quilted Matelasse Leather Upper Double Gg Logo On Side Thick Lug Sole Front And Back Pull On Straps 4.75” Shaft... more | go to store |
 | Principles Womens/Ladies Ofelia Leather Ankle Chelsea Boots - Brown - 7 Nice to meet you, new boots. Discover your favourite new pair in their collection of women's boots. Think heeled boots, knee highs, western, biker, hiker, Chelsea boots and ankle boots in a range of materials and colours. If you've got the plans, we've... more | $96.99 $46.70 go to store |
 | Women's Patricia Green Lug Sole Chelsea Boot - Black - Ankle boots A lug sole brings modern attitude to a utilitarian yet refined Chelsea boot grounded by a cushioned, arch-supporting footbed. 1" heel Pull-on style with elastic gore insets Cushioned... more | FREE shipping go to store |
 | Women's Pedro Garcia Zisca Lug Chelsea Boot - Gray - Ankle boots A velvety soft upper refines this cozy Chelsea boot lofted on a block heel and chunky lugs for street-chic elegance with a side of retro flair. 2 3/4" heel, 1" platform, 5" shaft, (size... more | $675.00 $270.00 FREE shipping go to store |
 | Breck Embellished Chelsea Boots Women's Karl Lagerfeld Breck Embellished Chelsea Boots - Natural - Ankle boots Suede & synthetic upper. Round toe. Side zip. Lining: Textile & synthetic. Trim: Crystal embellishment. Heel height, 2" (51mm). Platform height, 0.75" (19mm). Shaft height,... more | FREE shipping go to store |
 | J. Crew Shoes | J. Crew Green Rubber Waterproof Chelsea Rain Ankle Boots | Color: Green | Size: 9 These J. Crew Green Rubber Waterproof Chelsea Rain Ankle Boots Are Stylish And Purposeful! They Have Only Been Worn A Couple Of Times (Due To My Location And Not A Lot Of Rain). Size 9 Rubber Non-Slip Sole * There Are A Couple Of Marks On The Toe Of... more | go to store |
 | Shoes Are Lightly Worn But In Good Condition Otherwise Please See Pictures For Condition And Details 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 |
 | New Rebecca Minkoff Sabeen Too Chelsea Booties Leopard Print Cow Fur Ankle Boots Women's Size 7 Medium Width Brown...Black...Tan New Without Box...Former Display...Has Been Handled And Possibly Tried On...New Condition...Please View All Photos...Photos... more | go to store |
 | Kate Spade Shoes | Kate Spade Fringe Chelsea Ankle Boots Suede Tan Size 8 | Color: Tan | Size: 8 Kate Spade Fringe Chelsea Ankle Boots Suede Tan Size 8 Gently Used With Minor Wear. Great Preowned Condition. more | go to store |
 | J Crew Women's Chelsea Ankle Boots Brown Leather 03002 Size 9.5 Preworn Shaft Height (Measured From Top Of Heel To Top Of Boot) 5 Inches Heel 2 Inches Leather Made In Romania Really Comfortable! I Wore Them Many Times. Some Scuffs On The Front And... more | go to store |
 | Elevate Your Footwear Collection With These Stunning J. Crew Chelsea Ankle Boots. Crafted With Style And Quality, These Boots Are The Perfect Blend Of Fashion And Functionality. Key Features: Size: Women's 5 Material: Genuine Brown Leather Color: Light... more | go to store |
 | J. Crew Shoes | J. Crew Leather Chelsea Booties Ankle Boots Sz 7 | Color: Red/Tan | Size: 7 J. Crew Leather Booties In Deep Redwood Sz 7 In Awesome Condition, A Total Classic! more | go to store |
 | In Great Pre Loved Condition! These Are Sold Out In Stores Note: These Had Light Scuffs When Purchases Where Top Of Foot Would Be And Were Buffed Out. Not Noticeable As You Can See From Images But I Always Want To Disclose Everything! Pictures Cover... more | go to store |
 | Madewell Women’s Leather Western Ankle Chelsea Boots Off White Size 7.5 Pointed Toe Block Heel Ankle Height Shaft (Hits Slightly Lower Than The Stock Photo, Which Is Included For Style Reference Only) Leather Upper In Good Preowned Condition. See... more | go to store |
 | Pull On Boots. Leather Upper. Leopard Print. 1 Inch Heel. Gently Used, Still In Great Condition. * more | go to store |
 | J. Crew Shoes | J. Crew Matte Camo Chelsea Ankle Rainboots | Color: Black/Green | Size: 5 Very Good Condition. Normal Signs Of Wear. True To Size, Best Fits Size 5. Worn For 1 Rainy Season. more | go to store |
 | -Famous For Their Trendy Yet Functional Boots, J. Crew Has Done It Again With Their Chelsea-Styled Offerings This Season- Styled After The 1960's Mod Scene. -Made With Leather, This Boot Offers A Leather Upper And Lining. Hits At Ankle With 7/8" Heel.... more | go to store |
 | Brand New Zara Pull On Chelsea Boots With Lug Sole. Black Size 40 Or Us 9 Questions? Leave A Comment Below! more | go to store |
 | American Eagle Suede Chelsea Tan Ankle Bootie Boots Size 7 Sleek And Modern, With A Subtle Heel Tan Suede Slip On Style Low Profile Heel Approx Heel 1 3/4" Excellent Condition, No Issues Or Damage Quick Shipping Stop By My Closet And Take A Look... more | go to store |
 | *New With Tag. *Leather Upper. *Pull On Style. *Chunky Lug Sole/Heel. *Chelsea Style. *Inv#024760boxt. more | go to store |
 | Brown With Gold Flecks Sparkly Super Flattering Booties From Anthropologie. Lightly Worn (2-3) In Size 6.5. Slight Rub Mark As Shown In Pic Above. Very Comfortable more | go to store |
 | J.Crew Black Green Rubber Chelsea Boots Womens 7 Slip On Ankle Bootie. 1 Inch Flat Heel. These Shoes Are Pre-Owned, Cleaned, And Sanitized. Please Review All Pictures For Signs Of Wear. Smoke Free/ Pet Friendly Home Most Ship Next Day Bundle And Save... more | go to store |
 | Questions? Leave A Comment Below! more | go to store |
 | Coach Bowery Bead Black White Snakeskin Leather Chelsea Ankle Boots Women Size 6 Very Gently Used. No Rips Or Tears. Smoke-Free. No Box. I Always Carefully Package And Ship Asap. Reach Out With Any Questions! Pair In Photos Is The Exact Pair You Are... more | go to store |
 | J.Crew Women's Chelsea Ankle Boots Brown Leather 03002 Size 10 Good Pre-Owned Condition. Brown Leather Made In Romania more | go to store |
 | Madewell Snake Print Embossed Leather Low Chelsea Boot. Stacked Heel. New In Box. Size 6.5. Heather Natural Multi. more | go to store |
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