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| 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 Santoni Chelsea Boots, Ankle Boots - Blue - Casual boots Chelsea' suede ankle boots with elastic side inserts, contrast lining, back logo tab and rubber sole. Colours: Blue Composition: 100% leather Dimension: UK MEN MPN: MGSI13414SMAISYWU60.... more | $696.00 $454.00 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 |
 | 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 |
 | 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 |
 | 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: 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 |
 | Shield Square-toe Chelsea Ankle Boots Men's Burberry Shield Square-toe Chelsea Ankle Boots - Black - Casual boots 65% Calf Leather, 25% Polyester, 10% Rubber, Lining: 70% Calf Leather, 12% Polyester, 10% Goatskin Leather, 8% Rubber. Made in Italy. more | $1,106.62 $885.29 FREE shipping go to store |
 | Free People Tan Leather Ankle Boots Made In Spain Size 38/8 Euc No Box more | go to store |
 | Madewell The Bohnam Chelsea Boot Ankle Boots Booties Black Western Size 8.5. Leather Boots, Pointed Toe, Wood 2” Block Heel. more | go to store |
 | Burberry Shoes | New Burberry Chelsea Boots Check Leather Ankle Boots | Color: Black | Size: 7 New Burberry Check Chelsea Leather Ankle Boots Brand New In Box With Tags Full Set Eu 37 - Heel Measures Approximately 35mm/ 1.5 Inches - Black Leather - Pull On - Made In Italy 100% Brand New Authentic Guaranteed Professional Business Cross-Platform... 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 |
 | Ssense Exclusive Chelsea Boots Men's Toga Virilis Ssense Exclusive Chelsea Boots - Black - Casual boots Ankle-high polished leather Chelsea boots in black. Elasticized gusset at sides · Webbing pull-loops at collar · Graphic hardware at heel counter · Buffed leather lining · Foam... more | $580.00 $365.00 FREE shipping 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 |
 | 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 |
 | Anthropologie Ankle Boots - Leather Upper And Lining - Pull-On Style - Stacked Heels - Taupe/Tan - Size 9 Gently Pre-Owned; Some Light Scrapes To Heels As Shown. more | go to store |
 | Black Suede Leather Upper Ankle Height Booties Bow Detail In Back Chelsea Side Panels more | 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 |
 | Madewell Shoes | Madewell Bryce Suede Leather Chelsea Ankle Boots Tan Size 7 | Color: Tan | Size: 7 Madewell Bryce Suede Leather Chelsea Ankle Boots Tan Size 7 Small Stacked Heel, Pull Tabs, Elasticized Panels, And An Almond Toe. Gently Used With Normal Wear. Small Spot On The Left Boot Toward The Opening On The Front. Most Wear Is On The Bottom... more | go to store |
 | Some Wear But In Good Condition. 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 |
 | Madewell ‘The Grayson’ Chelsea Boot Black Leather Pointed Toe Ankle Booties Size: 10 Color: Black & Brown Style: J8293 Condition: Preloved Condition (Normal Signs Of Wear; Small Flaws To Leather Noted; Creasing At Toe Noted; Please See/Zoom In To All... 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 |
 | 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 |
 | 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 |
 | These Are Stylish, Comfortable, And Timeless Chelsea Boots From Free People. They Are Crafted From High Quality Genuine Leather That's Slightly Aged And Distressed. Gorgeous Dark Red/Burgundy/Oxblood Color. - Elastic Side Panels For An Easy Pull-On... more | go to store |
 | Kate Spade New York Leah Chelsea Block Heel Black Leather Ankle Booties Boots. Size 9.5. Pull On Boot. Leather Wrapped Heel. Gold Tone Spade On Back Of Boot 2.5" Block Heel In Very Good Pre-Owned Condition With Slight Signs Of Wear/Slight Wear On... more | go to store |
 | Madewell Shoes | Madewell Bryce Black Suede Chelsea Ankle Boot Size 9.5 | Color: Black | Size: 9.5 Madewell Black Ankle Boot Size: 9.5 Style Name: Byrce Style: M4674 Msrp: Was $158 Condition: Pre-Owned In Excellent Condition. Upper Suede Is In Pristine Condition, Outsole Has Minor Wear Heel: 3.25" Block Heel Features: Leather Upper And Lining,... more | go to store |
 | Madewell Shoes | Madewell Brown Leather Chelsea Ankle Boots | Color: Brown | Size: 7 Worn A Handful Of Times, In Fabulous Condition, Perfect For Fall more | go to store |
 | Questions? Leave A Comment Below! New Without Box more | go to store |
 | Free People Shoes | Free People Atlas Textile Chelsea Ankle Boots | Color: Black/Blue | Size: 38eu Rounded Toes ~ Ankle Height Shaft ~ Dual/Two Stretchy Gore Panels On The Sides Of The Ankle Shafts ~ Leather Panels On Toes And Heels ... With Scalloped Leather Trims Trimming The Gore/Stretch Panels ~ Woven Textile Panels On Top Of The Foot And On The... more | go to store |
 | Madewell Shoes | Madewell Sonia Chelsea Ankle Bootie Boot Snakeskin 6 | Color: Brown | Size: 6 Madewell Sonia Chelsea Boot Color: Brown Snakeskin Size 6 Style #M3463 Retail $188 New W/O Box 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... more | go to store |
 | Coach Suffolk Patchwork Black Leather Chelsea/Ankle Boots, Snakeskin, Calf, 6.5b Euc 1.25” Heel 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 |
 | Madewell Bryce Chelsea Suede Ankle Boot Low Heel Genuine Leather Suede Tan Camel Chestnut Brown Color - Neutral For Fall Pull On Style Terrific Condition Size 8.5 more | go to store |
 | Madewell Shoes | Madewell Grayson Black Leather Chelsea Ankle Boots 8 | Color: Black/Tan | Size: 8 Madewell Grayson Black Leather Chelsea Ankle Boots 8 Size 8. In Excellent New Condition. Black Leather. more | go to store |
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