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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 |
 | Eu Size 39 Excellent Condition Only Wore A Few Times Heel: 2.25 In Platform: 0.75 In more | go to store |
 | Listed For Sale Is A Pair Of Vintage Gray Nine West Patent Leather Stiletto Ankle Boots Condition: Vintage - Excellent Type: Patent Leather Ankle Boots Brand: Nine West. The Boots Feature A Side Zipper And Pointed Toe. Total Items Listed: 1 Pair Boots.... 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 |
 | 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 |
 | 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 |
 | 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 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 |
 | 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 |
 | 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 |
 | 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 |
 | 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 |
 | Men's Crown Vintage Farid Chelsea Boot - Brown - Casual boots Elevate your everyday style with the Farid Chelsea boots from Crown Vintage. These shoes feature a classic silhouette with a leather exterior for a touch of luxury. Leather upper. Pull-on... more | go to store |
 | Men's Crown Vintage Glory 2 Chelsea Boot - Brown - Casual boots The Glory 2 Chelsea boot from Crown Vintage rocks a classic design that effortlessly upgrades any outfit. The soft leather upper adds a tailored finishing touch. Leather upper. Pull-on... more | go to store |
 | Men's Crown Vintage Hilde Chelsea Boot - Brown - Casual boots The joys of fall include pumpkin spice lattes, bonfires, and experiencing all four seasons in one day. While the last one may be more of an annoyance, the Hilde Chelsea boots from Crown... more | $59.99 $49.98 go to store |
 | Men's Crown Vintage Hilde Chelsea Boot - Brown - Casual boots The joys of fall include pumpkin spice lattes, bonfires, and experiencing all four seasons in one day. While the last one may be more of an annoyance, the Hilde Chelsea boots from Crown... more | $59.99 $47.98 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 |
 | Used Pair Of Madewell Nadine Ankle Chelsea Boots In Size 7.5. These Are A Spotted Calf Hair Upper. There Is A Little Wear On The Points Of The Toes. Minimal Heel Wear. Please See Photos 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 |
 | Brand New In Box. Womens Us Size 8. Runs Big More Like 8.5. Please See Photos For Added Description more | go to store |
 | Madewell Ainsley Chelsea Boots. Black Ankle Pull On Leather Booties In Great Preloved Condition. Still Have Lots Of Life! See Images For Details Of Wear. Genuine Leather Upper, Lining And Sole. 3/4” Heel. Size: 7.5 more | go to store |
 | Beautiful Boots more | go to store |
 | Coach Tia Ankle Chelsea Boots, Chunky Heels, Wine Color Suede Booties, Size 8.5 Women’s. Preowned. Some Wear From Normal Use, Mainly On The Bottoms. Heel Height Approx 2.5”. Elevate Your Shoe Game With These Stylish Coach Tia Ankle Booties In A... 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 |
 | Anthropologie Boots Leather Lace Up Shoes Black Size 37 Preowned Item In Excellent Overall Condition. No Odors, Stains, Or Holes. more | go to store |
 | New With Box Free People James Tan Brown Leather Chunky James Chelsea Ankle Boots Inside Zippers, Chunky, Apx 3.5" Heel, 1" Platform Size 41 more | go to store |
 | Reposhing This Item I Purchased From @Mltldl. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! more | go to store |
 | Euc Kate Spade Bellamy Ankle Booties Stone - Light Grey , Mauve Undertone Gold Hardware Size 9.5 Leather Rubber Sole Shaft Measures Approximately 4.5" From Arch Heel Measures Approximately 1" Platform Measures Approximately 0.25 Boot Opening Measures... more | go to store |
 | Free People Atlas Chelsea Bootie Black Leather Fabric 40 New Without Box Tufts Of Faux Shearling Woven Into A Jacquard Pattern Create Eye-Catching Texture On This Mixed-Media Version Of A Classic Chelsea Boot. Studded Patchwork Look 5 1/2" Shaft... more | go to store |
 | Brand - Free People Size - Eu 39.5 / Us 9.5 Excellent Preowned Condition Ankle, Chelsea, Studded Trim, Scalloped Lace Trim, Pull On, Side Stretch, Suede, Leather, Round Toe, Comfortable, Hiking, Causal, Winter, Fall, Combat, Booties more | go to store |
 | Coach Snake Skin And Leather Patchwork Chelsea Ankle Boots Size: 8.5 Black Good Used Condition-Flaws Include Some Scrapes Of Normal Wear And Some Fading On The Suede Otherwise In Good Condition Tags: Fall, Autumn, Western Boots, Boots more | go to store |
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