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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 |
 | Brand New With Box Suede & Leather Upper Leather Insole Rubber Sole Stacked Leather Heel Pull On Styling Made In Spain Heel Height 1” Shaft Height 5” more | go to store |
| Best Seller  | 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 |
 | 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 |
 | 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 |
 | Women's Ann Demeulemeester Black Drees Chelsea Boots - Ankle boots Ankle-high buffed calfskin boots in black. more | $1,475.00 $870.00 FREE shipping go to store |
 | Excellent Condition Madewell The Carina Boot In Snake Embossed Leather Ankle Chelsea Boot Booties Brand: Madewell Size: Women’s Size 6 Style: 2030756 Carina Color: Burnt Clay Multi 1.5” Stacked Block Heel 5.5” Tall Leather Upper Snakeskin Print Yellow... 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 |
 | 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 |
 | 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 |
 | Reposhing This Item I Purchased From @Deenajwhennen. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! 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 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 |
 | Men's Ann Demeulemeester Ernest Ankle Boots In Leather - Black - Casual boots Ernest Ankle Boots in Black Leather. Condition: New with Tag. Sole: Leather. Closure: Side zip. Toe Shape: Round. Material: Leather. Fit: True to size - Sizing European.... more | $945.79 $599.25 FREE shipping go to store |
 | Men's Ann Demeulemeester Kornelis Ankle Boots - Black - Casual boots 100% Calf Leather. Made in Italy. more | $1,025.95 $610.65 FREE shipping go to store |
 | Coach Shoes | Coach Ann Camel Walnut Pebbled Leather Ankle Boots | Color: Brown | Size: 10 Statement Leather Booties With 3.75 Inch Heels. Versatile, Can Be Worn Casually Or Dressed Up. - Preowned In Good Condition With Minor Wear - See Photos For Any Flaws/Wear/Discolorations - Color May Differ Slightly Due To Lighting. Size Is Determined... more | go to store |
 | Coach Shoes | Coach Ann Tan Suede Ankle Boots Size 8 | Color: Brown/Tan | Size: 8 Coach Ann Tan Suede Ankle Boots Size 8 Tan Suede Saddle Tan Leather Straps With Gold Hardware Almond Toe Zipper In Back For Easy On And Off Buckle At Side Allows You To Adjust Tightness Very Gently Worn--Some Light Scuffing On Soles (See Photo) All... more | go to store |
 | Converse Shoes | Converse Chuck Taylor All Star Chelsea Boot High | Color: Brown | Size: 8 Good Condition Size 8 Offers Welcome more | go to store |
 | J. Crew Shoes | Black Chelsea Ankle Boots 6.5 | Color: Black | Size: 6.5 These Are Black Chelsea Ankle Boots That I Wore So Religiously That I Bought Two Pairs When They Were On Sale As Back Up. I Don’t Need Two Extra Pairs Tho So I’m Selling These Now. Have Hardly Been Worn But Were In Storage For A While And They Deserve... more | go to store |
 | Free People Shoes | Free People Castillo Chelsea Boots Ankle Size 38 | Color: Brown/Red | Size: 8 Free People Castillo Chelsea Boot - Size 38 Eu/ Us Women’s 8. Fits Size 8.5 Snug. Purchased From Free People Directly Years Ago And Held Onto Them Because They’re So Cute But Unfortunately A Little Too Small For Me. Made With Real Patent Leather And... more | go to store |
 | Kate Spade Garden Gray/ Truffle Suede Scalloped Chelsea Ankle Boots Beautiful Graphite Dark Truffle Gray Slip On Style With Side Gore Panels Feminine Scallop Details Sweet Back Heel Bow Round Toe Cushioned Insole Leather Sole 3” Block Heel Made In... more | go to store |
 | In Good Condition, See Last Pictures For Some Slight Scratches (Not Visible While Wearing!) Textured Rubber Heel. Pull Tab In Back For An Easy On/Off. Padded Footbed. 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 |
 | Condition: Pre-Owned With Natural Cosmetic Wear Noted, See Photos. Size: 6 Color: Tan Material: Suede Leather Upper Measurements: Shaft Height: 4.5 In Heel Height: 1.75 In Made Of Textured Suede With A Comfy Elasticized Shaft And Grippy Lugsoles, This... 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 |
 | Madewell Shoes | Madewell Carina Ankle Chelsea Boot Bootie | Color: Brown | Size: 7 Excellent Condition! Size 7 Cognac Color 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 |
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