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| 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 |
 | Tough Meets Chic In This Citified Boot. A Lighter, More Wearable Version Of A Boot Iconand It Hits The Perfect Height For Both Jeans And Dresses. Hint: Go Ahead And Break Them Inthey Only Get Better With Age. Brand: Madewell Item: The Biker Boot Style... 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 |
 | ® Hillmont Chelsea Leather Cold Weather Boots|dress Shoes Men's Ugg ® Hillmont Chelsea Leather Cold Weather Boots|dress Shoes - Brown - Casual boots Sleek and functional, our take on a traditional chelsea silhouette incorporates seam-sealed waterproof leather for enhanced protection from the elements. Even... more | $190.00 $132.99 go to store |
 | ® Hillmont Chelsea Leather Cold Weather Boots|dress Shoes Men's Ugg ® Hillmont Chelsea Leather Cold Weather Boots|dress Shoes - Brown - Casual boots Sleek and functional, our take on a traditional chelsea silhouette incorporates seam-sealed waterproof leather for enhanced protection from the elements. Even... more | $190.00 $132.99 go to store |
 | Free People James Chelsea Boot 10 / 40 New Nib Tan Chunky Sole Boots A Cool Take On A Classic Style Boot Chunky Rubber Lug Sole With Soft Leather Upper Elastic Details With Side Zip Almond Toe Cushioned Insole Approximately 3.5" Heel Height Size 10... 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 |
 | An Elastic Gore Inset Makes For Easy-On Styling In This Leather Bootie That'll Carry You Through Every Season. Leather And Textile Upper/Textile Lining/Rubber Sole Made In Spain more | go to store |
 | Anthropologie Shoes | Brown Leather Chelsea Boots | Color: Brown | Size: 9 Like New Brown Chelsea Boots From Anthropologie. Have Only Been Worn Once. 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 |
 | J. Crew Shoes | J. Crew Cognac Caramel Brown Leather Chelsea Boot | Color: Brown | Size: 10 J. Crew Cognac Caramel Brown Leather Chelsea Boot Size 10 In Excellent Condition One Small Area Of Watermarks As Seen In Photo But Not Noticeable When Worn 100% Leather Rubber Sole more | go to store |
 | J. Crew Shoes | J Crew Chelsea Leather Brown Boots | Color: Black/Brown | Size: 7 J Crew Chelsea Leather Brown Boots, Brand New, Never Worn And In The Original Box. Heel Hight About 2". more | go to store |
 | Brand New In Box (Box Lid Seams Dented/Busted, Shipped To Me That Way) - All Inserts And Stuffing Included As Well. Absolutely Gorgeous Boots! Purchased And Wound Up Wearing My Black Ones More And Never Got To These Before The Weather Changed! Now... more | go to store |
 | Free People James Chelsea Platform Boot Size: 8 Side Zip Closure Cushioned Insole Leather Upper And Lining/Rubber Sole Made In Spain A Chunky Block Heel And Lugged Sole Bring Sturdy Utilitarian Height To A Classic Chelsea Boot With Hidden Elastic-Gore... more | go to store |
 | Cute, Classic, Now Even More In Style With A Longer Hemmed Straight Leg Jean (Hello The Good Parts Of The 90s!). Good, Used Condition. Check The Photos. Super Comfortable. Still Tons Of Life Left In These Babies. more | go to store |
 | Madewell Shoes | New Madewell Bradley Chelsea Brown Boots Size 7 1/2 | Color: Brown | Size: 7.5 New And Never Worn Size 7 1/2. Description From Website Hit The Streets In This Classic Pull-On Chelsea Boot With Superchunky Lug Soles. The Wide Elastic Gore Not Only Looks Cool, But Also Makes On-And-Offs So Easy. And, Cushiness Alert: Our Mwl... more | go to store |
 | New With Out Tag!!! Free People Brown Atlas Studded Chelsea Leather Booties Ankle Boots In Size 8 Eur 38.5 Patent Leather And Suede Studded, Brogued And Scalloped Trims 1 1/4” Heel 1/2” Platform Pull On Style With Elastic Gore Insets Leather Upper And... more | go to store |
 | Some Wear But In Good Condition. more | go to store |
 | Columbia Fairbanks Rover Chelsea Brown Men's Boots Size 11 Size: 11 Color: Brown Material: Leather Condition: New With Box. more | go to store |
 | Coach Shoes | Coach Brown Leather Chelsea Boots | Color: Brown | Size: 8.5 Coach Brown Leather Chelsea Boots. ***Note: These Are 8.5 But Fit A 9 Too. Normal Wear, Pre Loved Condition. Small Nicks On The Heel And Scuffs On The Leather. Slip-On. Elastic Panel. Small Block Heel. Rounded Toe. more | go to store |
 | American Eagle Ae Chelsea Boot Men's Size Leather Brown Mid Top Alsu01305 Brand New No Box. 100% Authentic! A Timeless, Pair-With-Everything Chelsea Boot With A Genuine Suede Finish! Pull-On Boot With Elastic Side Panel Suede Upper Heel Loop Elevated Heel 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 |
 | J. Crew Shoes | J Crew Brown Chelsea Boots | Color: Brown | Size: 6.5 J Crew Brown Leather-Style Chelsea Boots. Worn Exactly Once, Barely Any Wear On Them. Size 6.5 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 |
 | New Without Box Free People Essential Chelsea Boots In Chocolate Brown. Retail $198. Size 7.5. Shown Modeled In Other Colors For Styling And Fit. This Listing Is For The Chocolate Brown. A Wardrobe Essential, These Spanish-Made Leather Chelsea Boots... more | go to store |
 | Free People Atlas Chelsea Booties Brown Studded Leather Boots | Size 7.5us Brand New Shaft Measures Approximately 6" From Arch. Heel Measures Approximately 1.25 Inches" Bring In The Winter Season With The Ruggedly Chic Details Of The Free People Atlas... more | go to store |
 | Coach Shoes | Coach Mens Brown Leather Chelsea Boots | Color: Brown | Size: 9.5 Brand New, Never Worn. No Box But Still In Plastic. Questions? Leave A Comment Below! more | go to store |
 | Questions? Leave A Comment Below! Like New Condition more | go to store |
 | Zara Shoes | Brown Leather Chelsea Boots | Color: Brown | Size: 11 Brown Leather Chelsea Boots Size 11/44 Lightly Used. Some Signs Of Wear. Still Like New. more | go to store |
 | Ralph Lauren Shoes | Brown Ralph Lauren Chelsea Boots | Color: Brown | Size: 9 Super Cute Brown Leather Slip On Ralph Lauren Boots. Pointed Toe. Amazing Condition more | go to store |
 | J Crew Cognac Brown Leather Chelsea Boots With Stretch Panels For Easy Pull-On. Tag Size 8. Fits 7.5-8 In My Opinion. Style Eo824 Preowned. Shows Signs Of Wear Including Scuffs On Toes, Wear On Back Heels, Wear On Bottoms Of Soles, Creasing In Midfoot... more | go to store |
 | Madewell Shoes | Madewell Brown Chelsea Boots | Color: Black/Brown | Size: 7 Brown Leather Chelsea Boots From Madewell, Size 7. Lightly Worn, Very Comfortable. Love Them But Don’t Fit Me Perfectly more | go to store |
 | New In The Box True To Size Luxe Suede Wedge Bootie With Topstitching And A Pointy Toe. An Elasticized Cuff With Deep Side Goring Makes For A Svelte Custom Fit. 2 3/4" Heel 4 1/2" Boot Shaft. Stretches To Fit Side Zip Closure Leather And Textile Upper... more | go to store |
 | Questions? Leave A Comment Below! Nwot more | go to store |
 | Coach Shoes | Coach Graham Chelsea Mahogany Brown Pull-On Boots Sz 12 D | Color: Brown | Size: 12 Perfect Condition - Another Pair Of Shoes/Boots Sitting In My Son’s Closet - Once Bought, Could Not Get Comfortable On His Weird Wide Feet. Leather Boots, Pull Tab, Rubber Sole, C3102, Size 12 D. 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 |
 | Madewell Chelsea Boot, Size 8.5 In Brown Apple Butter Color. Crafted Of Smooth Leather, This Chelsea Boot Has An Almond Toe And Stacked Heel. Minimal Yet Supercute, They Are Comfy Enough To Take From Day To Night , Thanks To Mwl Cloudlift Lite Padding... 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 |
 | Coach Shoes | Coach Geneva Chelsea Boot In Brown Maple Leather Size 11 New | Color: Brown | Size: 11 Brand New! Size 11 A Timeless Chelsea Look Goes To The Next Level With Modern Appeal In The Slender Heels And Versatile Pull-On Design Of The Coach Geneva Booties. 3" Heel Leather Rubber Sole more | go to store |
 | Coach Shoes | Coach Delaney Brown Leather And Wool Chelsea Boots Size 9 | Color: Brown | Size: 9 Label: Coach Condition: Good (See Guide Below) Flaws: Overall Wear/A Few Leather Scuffs/A "Chip" In The Heel Marked Size: 9b Measurements: (Refer To Pics) Description These Chunky Gems Are So Great. Note Flaws. Clean Interiors. Heels Might Clean Up... more | go to store |
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