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| Best Seller  | 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 |
 | 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 |
| Best Seller  | 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 |
 | Relatively Lighter Wear, Pre-Owned Condition, But Not Totally Without Blemish. Color: Cream Leather Vamp Side Zipper For Ease Of On And Off Cushioned Interior Foot Bed Expandable Accent Inset For Optimal Comfort Fit Approximate Measurements 6” Shaft... more | go to store |
 | Ssense Exclusive Chelsea Boots Men's Toga Virilis Ssense Exclusive Chelsea Boots - Black - Casual boots Ankle-high buffed leather Chelsea boots in black. Zip closure · Concealed elasticized gusset at sides · Webbing pull-loop at heel collar · Graphic hardware at heel counter ·... more | FREE shipping go to store |
 | Sasha Lug Chelsea Boot - Black - DKNY Boots Women's DKNY Sasha Lug Chelsea Boot - Black - Ankle boots Thick lugs and a flared platform lend futuristic design lines to a sleek Chelsea boot featuring a rear zip with branded hardware. more | FREE shipping 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 |
 | Essential Chelsea Boot - Natural - Free People Boots Women's Free People Essential Chelsea Boot - Natural - Ankle boots A basket-weave motif adds subtle texture to a block-heel Chelsea boot that instantly refines your look. 2 1/2" heel 6 1/2" shaft Back zip closure; elastic gore insets Leather... more | FREE shipping go to store |
 | Sahara Block Heel Chelsea Boot - Black - Paul Green Boots Women's Paul Green Sahara Block Heel Chelsea Boot - Black - Ankle boots A treaded sole and stacked block bring a touch of edge to this round-toe Chelsea boot featuring flexible hidden gore insets and a side zip for easy on and off. 3 1/4" heel; 3/4"... more | $520.00 $360.00 FREE shipping go to store |
 | Frye Alton Chelsea Ankle Boot - Brown Say hello to the perfect, most versatile boot. The ankle height makes this style easily transition from day to night. Wear them with your favorite skinny jeans and tee for a more laid back look, or pair them with your favorite mini dress and jacket for... more | $320.00 $187.00 go to store |
 | Vance Co. Shoes Vance Co. Men's Pratt Ankle Boot - Black - 8 These men's Chelsea boots by Vance Co feature premium faux leather uppers that rise to the ankles with stylish distressed faux leather detail and zipper accent. Top-stitching borders treaded outsoles with sturdy block heels to complete the style. Heel... more | go to store |
 | Vance Co. Shoes Vance Co. Men's Pratt Ankle Boot - Black - 10 These men's Chelsea boots by Vance Co feature premium faux leather uppers that rise to the ankles with stylish distressed faux leather detail and zipper accent. Top-stitching borders treaded outsoles with sturdy block heels to complete the style. Heel... more | go to store |
 | Anthropologie Shoes | Aa Copenhagen Red Waxed Suede Chelsea Ankle Boot 36 New | Color: Red | Size: 6 Actual Item Shown In Pictures. Brand: Aa Copenhagen Model: Chloe Condition: New With Box Style: Modern Fashion Antiqued Ankle Boots Size: Ladies Euro 36 Measurements: Shaft Height: 6 In. Height Without Heel Heel: 1 In. Shaft Circumference: 10 In.... 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 |
 | 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 |
 | Free People James Leather Chelsea Ankle Boots White Size 41 Equivalent To Us 11 Side Zip Elasticized Inset Cushioned Footbed 6" Shaft Height 3.5" Inch Chunky Heel With 1" Platform New In Box more | go to store |
 | Kate Spade New York Edimburg Black Chelsea Ankle Rain Boot New Size 11 New Without Original Box Approx 1-1/2" Heel Round-Toe Pull-On Boots With Goring At Sides Gold-Tone Piping At Welt Back Heel Tab Upper And Outer Sole: Polyvinyl Chloride; Inner... more | go to store |
 | New With Box Size 38.5 / Us 8.5 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... more | go to store |
 | Coach X Tabitha Simmons Velvet Black Chelsea Ankle Booties Velvet Upper Man-Made Leather Lining And Footbed Rubber Outsole Zip Closure Shaft: 4 1/2" Height, 9" Circumference 1" Heel This Special Collaboration Between Coach And Designer Tabitha Simmons... 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 |
 | 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 James Leather Chelsea Ankle Boots White Size 36 Equivalent To Us 6 Side Zip Elasticized Inset Cushioned Footbed 6" Shaft Height 3.5" Inch Chunky Heel With 1" Platform New In Box more | go to store |
 | Madewell The Bryce Chelsea Suede Stocked Heel Ankle Boots Side Zipper Women Size 8 Almond Toe 2.5” Heel Small Scuff See Photos more | go to store |
 | Free People Arlo Santa Fe Croc Embossed Chelsea Ankle Boots Tan Size 37. Fit Close To A Larger Size 7.5 Has A Small Scuff Along Right Shoe On Front. Minimal, However Excellent Pre-Owned Condition Otherwise True To Size* Amp Up Your Style In Thie Arlo... more | go to store |
 | Free People James Leather Chelsea Ankle Boots White Size 39.5 Equivalent To Us 9.5 Side Zip Elasticized Inset Cushioned Footbed 6" Shaft Height 3.5" Inch Chunky Heel With 1" Platform New In Box more | go to store |
 | Free People Shoes | Free People James Chelsea Ankle Velvet Boots | Color: Black | Size: 37 Free People James Chelsea Crushed Velvet Chunky Sole Ankle Boot A Chunky Block Heel And Lugged Sole Classic Chelsea Boot Slim Silhouette Bootie Side Zip And Elasticized Insert Details Cushioned Footbed 3,5 “ Chunky Heel With 1” Platform Almond Toe... more | go to store |
 | Free People James Leather Chelsea Ankle Boots White Size 36 Equivalent To Us 6 Side Zip Elasticized Inset Cushioned Footbed 6" Shaft Height 3.5" Inch Chunky Heel With 1" Platform New In Box more | go to store |
 | Nwot Free People Essential Chelsea Ankle Boot Deep River Teal Leather * Size: Eu Size 38 (Us Size 7.5 Per Free People) * Color: Deep River (Teal Green/Blue) * Faded Leather Uppers * Back Zipper Closure * Elastic Side Gore Panels * Cushioned Insoles *... more | go to store |
 | Free People James Leather Chelsea Ankle Boots White Size 39 Equivalent To Us 9 Side Zip Elasticized Inset Cushioned Footbed 6" Shaft Height 3.5" Inch Chunky Heel With 1" Platform New In Box more | go to store |
 | Free People James Leather Chelsea Ankle Boots White Size 41 Equivalent To Us 11 Side Zip Elasticized Inset Cushioned Footbed 6" Shaft Height 3.5" Inch Chunky Heel With 1" Platform New In Box more | go to store |
 | 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 Insole... more | go to store |
 | Madewell Booties Bryce Suede Leather Chelsea Ankle Black Size 10 Style M4674. Madewell Bryce Ankle Boots Booties Black Suede Leather M4674 Side Zip Biker Westernexcellent Condition more | go to store |
 | Free People Shadow Lark Ankle Chelsea Bootie Sz 6 Navy Perforated Leather Hidden Snaps On One Side Side Zipper On Other Side Ankle Boots, Chelsea Style Small Heel Cute Stitched Detail On Side Size 36 Pre-Owned Have Some Wear But Still Lots Of Left... more | go to store |
 | Ankle Height Booties Square Toe Pull On Style No Zip more | go to store |
 | American Eagle Outfitters Shoes | American Eagle Chelsea Boots | Color: Brown/Tan | Size: 9 Really Cute Chelsea Boots Size 9. Worn Only A Few Times In Great Condition. Beautiful Quality Leather Material. Ankle Height, Zip Closure. more | go to store |
 | Free People Shoes | Free People Brown Lugs Brooks Chelsea Suede Boots. New | Color: Brown | Size: 8 Suede Leather Upper Ankle High Leather Upper (Suede) Zipper Closure Lightly Cushioned Foot Bed Luv Outsole Size 38 (8) more | go to store |
 | Free People Shoes | Free People Brooks Lug Sole Chelsea Boots | Color: Cream | Size: 10 A Contemporary Spin On The Classic Chelsea Style, These Timeless Ankle-Covering Boots Feature A Chunky Sole For An Exaggerated Look. A Neutral Boot To Pop Any Outfit Fp Collection Color Chalk Artisan Crafted From Fine Leathers And Premium Materials, Fp... more | go to store |
 | Free People Shoes | Free People James Ice Leather Chelsea Boots | Color: Gray/White | Size: 36eu The Free People James Ice Leather Chelsea Boots Are A Modern Twist On A Beloved Classic. Smooth, Slightly Distressed Genuine Leather Shapes These Trendy Chelsea Boots That Have An Almond Toe And An Ankle-High Shaft With Contrasting Tan Gussets And Seam... more | go to store |
 | Free People Essential Chelsea Boots Size 6 A Wardrobe Essential, These Spanish-Made Leather Chelsea Boots Feature A Faded Design With A Stacked Heel. Zipper Back Closure Cushioned Insole Elastic Side Accents Leather Upper Shaft: 6.42 In Ankle... more | go to store |
 | Free People Shoes | Free People Brooks Lug Sole Chelsea Boot | Color: Black | Size: 8 Free People Brooks Lug Sole Chelsea Boot In Good Pre Owned Condition. Some Parts Can Use A Brushing As Can Be Expected With Suede. Some Very Minimal Creasing On Ankle Part. Please See All Pictures For Wear. Minor Wear On Soles. Features A Super-Chunky... more | go to store |
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