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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 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 |
| Best Seller  | 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 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 |
 | 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 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 |
 | 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 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 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 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 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 |
 | Madewell Ivy Chelsea Mini Dot Animal Print Ankle Boots Calf Hair Size 7 Like New 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 |
 | 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 |
 | Men's Givenchy Black Show Chelsea Boots - Casual boots Ankle-high brushed bullskin Chelsea boots in black. more | $1,095.00 $548.00 FREE shipping go to store |
 | Men's Marni Black O-ring Chelsea Boots - Casual boots Ankle-high patent leather Chelsea boots in black. more | $1,250.00 $850.00 FREE shipping go to store |
 | Black 2976 Gothic Americana Quad Chelsea Boots Men's Dr. Martens Black 2976 Gothic Americana Quad Chelsea Boots - Casual boots Ankle-high polished leather Chelsea boots in black. more | go to store |
 | New Madewell Sonia Snake Embossed Low Chelsea Block Heel Ankle Boots Size 7.5 - Almond Toe Tapered, Stacked Heel - Chelsea Boot - 1 3/4" Heel, 3" Shaft - Pull-On Style - Elastic Gore Insets - Cushioned Footbed - Leather Upper And Lining/Synthetic Sole... more | go to store |
 | Good Preowned Condition. Light Wear As Shown In Photos. An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. Pull-On Style With Elastic Gore Insets Cushioned Footbed... more | go to store |
 | New Without Box (Has Tags) Multiple Sizes Available Free People Beau Western Ankle Chelsea Boot Embossed Gold Leather Embossed Reptile Genuine Leather Chelsea Western Style Gold Metallic Block Heel 1.5" Pointed Toe Made In India. Elastic Side Gussets.... more | go to store |
 | Gucci Cordovan Lux Pointed Toe Side Buckle Chelsea Ankle Boots Great White Size 37 New With Dustbags, No Box, Very Minor Signs Of Retail Environment Try Ons As Photographed, Size 37, Per Brand Equivalent To Us Size 7, Authenticity Guaranteed. All... more | go to store |
 | Madewell Spencer Taupe Chelsea Slip On Leather Ankle Boots Slip On Stacked Block Heel Chelsea Style Ankle Length Western Leather Upper And Lining Taupe Color Size: 8.5 Condition: Good, Has Some Scuffing more | go to store |
 | Bran New In A Box. Size 7.5 But They Run 1 Size Bigger =8.5. Genuine Embossed Croc Leather. Black Elastic Sides, Pointy Toe. Curved Hills 1.75” more | go to store |
 | Designer: Gucci Size: Marked As 11 / Us 11.5 (Conversion Per Designer's Website) Condition: Authentic And Brand New Style Name / Number: 624661 Cdzk0 1000 Material: Leather Upper, Leather Unique Features: Classic Black Leather Mens Chelsea Ankle Boots.... 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 |
 | Free People Arlo Santa Fe Ankle Boots Size: European 37.5 (Us 7) Color: Black Crocodile Basically Brand New. Sales Sticker Still On Sole. Only Worn Once. Condition: These Shoes Are Intentionally Distressed. Brand New, They Intentionally Look Worn In,... more | go to store |
 | Coach Shoes | Coach Bowery Chelsea Ankle Boot In Burgundy | Color: Brown/Red | Size: 5 The Bowery Chelsea Boot From Coach Takes A Classic Silhouette And Updates It With Modern Appeal. This Ankle Bootie Features A Sleek Almond Toe And Ombre Block Heel For An Eye-Catching Finish. Details: * Runs Large, Fits Like Size 6 * Suede Upper *... more | go to store |
 | Anthropologie Size 7.5 Brown Suede Metallic Chelsea Ankle Booties Boots. Great Pre-Owned Condition more | go to store |
 | Deena & Ozzy Moto Ankle Chelsea Boots From Urban Outfitters. Elastic Ankle And Gold Belts Details. Good Used Condition, See Photos For Condition. more | go to store |
 | Gucci Shoes | Gucci Chelsea Horsebit Chain Ankle Boots Size 40 | Color: Black | Size: 10 Excellent Used Condition Gucci Chelsea Boots With Horsebit And Chain Detail. Retailed For $1,150 Plus Tax. Includes Original Box And 2 Dust Bags Black Leather 1.5 Inch Heel Gold Horsebit Silver Chain Take A Look At All Pics For Signs Of Wear more | go to store |
 | Note: Shoes Are Different Sizes, Left Shoe Is 37.5, Right Shoe Is 38.5 New Free People Atlas Chelsea Leather Puffer Upper Ankle Boots Black Size 7.5 - 8.5 Featuring All-Over Stud Detailing And Brogued And Scalloped Trims For An Eye-Catching Look, The... more | go to store |
 | Madewell Shoes | Madewell Metallic Gold Chelsea Ankle Boots As Is | Color: Gold | Size: 7 Gorgeous And Practical Leather Ankle Boots. Marked As Is Because They Need To Be Re-Soled; Sole Of One Boot Cracked At The Heel Seam. Lots Of Life Left Once They Are Resoled - I Don’t Have A Local Cobbler Or I Would Do It. more | go to store |
 | Madewell Shoes | Madewell Ryan Black Leather Chelsea Ankle Boot Size 9.5 | Color: Black | Size: 9.5 Madewell Black Ankle Boot Size: 9.5 Style Name: Ryan Style #: E2331 Msrp: Was $158 Condition: Pre-Owned In Excellent Condition. The Upper Leather Is In Pristine Condition, Lower Has Normal Wear And Tear. Heel: 3.25" Features: Slip On Styling With... more | go to store |
 | Beautiful Patchwork Ankle Boot Gently Worn And Still Has A Lot Of Life Left In Them more | go to store |
 | Excellent Condition ... No Flaws!! Bundle And Save 20%... Free Shipping On All Bundles! ~ Offers Welcome! ~ Fast Shipping! ~ For Offers European Size 40 Appreciate Your Wonderful Sense Of Style And Make A Statement In These Jaw-Dropping Chelsea Boots... more | go to store |
 | Madewell Regan Chelsea Ankle Boot In English Saddle. Made Of Rich Leather, These Cool Pull-On Boots Have Block Heels For A Little Extra Height. Color: Brown Size 7.5 Condition : Preloved, No Rips, Holes Or Tears. Normal Signs Of Wear. No Modeling... more | go to store |
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