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| Best Seller  | ® Skyview Chelsea Suede Boots|dress Shoes Men's Ugg ® Skyview Chelsea Suede Boots|dress Shoes - Brown - Casual boots Constructed from waterproof suede and reinforced with sealed seams, the Skyview promises protection against light showers. This timeless chelsea design is primed for the winter... more | $160.00 $87.99 go to store |
 | ® Burleigh Chelsea Leather/waterproof Boots|dress Shoes Men's Ugg ® Burleigh Chelsea Leather/waterproof Boots|dress Shoes - Black - Casual boots The Burleigh Chelsea offers the fashionable presence of a sneaker with the functionality and sleek profile of a Chelsea boot. With a waterproof leather upper,... more | FREE shipping go to store |
| Best Seller  | ® Skyview Chelsea Leather Boots|dress Shoes Men's Ugg ® Skyview Chelsea Leather Boots|dress Shoes - Black - Casual boots Constructed from water-resistant leather and enhanced with sealed seams, the Skyview emerges as an ageless chelsea boot tailored for winter and subsequent seasons. Its... more | $160.00 $103.99 go to store |
 | A Pointed Toe And Stacked Heel Kick Up The Western Style Of This Leather Chelsea Boot That Will Lead To New Outfit Frontiers. 2" Heel 6" Shaft Leather Upper And Lining/Synthetic Sole New No Tags Or 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 |
 | Madewell Shoes | Madewell Bryce Chelsea Boot Tan Suede Boots | Color: Tan | Size: 8 Madewell Bryce Chelsea Boot Tan Suede Boots Pre Owned Good Condition Size 8 Please See All Pics For Best Description Streamlined And Undeniably Cool, This Suede Chelsea Boot Has A A Low-Key Western Vibe We Love. Cuff Up Or Tuck In Your Jeansthese Hit... 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 $75.99 go to store |
 | ® Hillmont Chelsea Leather Cold Weather Boots|dress Shoes Men's Ugg ® Hillmont Chelsea Leather Cold Weather Boots|dress Shoes - Black - 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 $75.99 go to store |
 | ® Burleigh Chelsea Suede/waterproof Boots|dress Shoes Men's Ugg ® Burleigh Chelsea Suede/waterproof Boots|dress Shoes - Brown - Casual boots The Burleigh Chelsea offers the fashionable presence of a sneaker with the functionality and sleek profile of a Chelsea boot. With a waterproof suede upper,... more | FREE shipping 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 $75.99 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 Eu Size 38 And 38.5 Nwob Location Bin 36 more | go to store |
 | Madewell Shoes | Madewell Rubber Rain Boots Chelsea Boots Black Size 10 | Color: Black | Size: 10 Great Rain Boots In Good Condition-/ Please Note That There Is Some Separation In The Rubber On The Right Heel. Priced Accordingly 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 Eu Size 38.5 Nwob Location Bin 36 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 |
 | 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 |
 | Sold Out Everywhere! Size 7 The Grayson Chelsea Boots . Amber Brown Color Suede Boots 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 |
 | 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 |
 | Ralph Lauren Shoes | Lauren Ralph Lauren Tally Rain Boot Chelsea Boot Ankle | Color: Black | Size: 9 Black Ankle Rain Boots. Some Scratching Along The Side. Narrow Sizing. more | go to store |
 | Free People Boots James Chelsea Boots In Black Leather Sz Eu 40 Nwot (Us 10) 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... more | 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 |
 | Great Preowned Condition Questions? Please Ask! more | go to store |
 | Madewell Shoes | New Madewell Regan Boot Chelsea Boot Calf Hair | Color: Brown/Tan | Size: 7 Made Of Leopard-Print Calf Hair, These Cool Pull-On Boots Have Block Heels For A Little Extra Height (That's Still Walking-Friendly). Cushiness Alert: We've Added An Extra Layer Of Padding To Make Them Even Easier On The Feet. This Cool Pull-On Boot... 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 |
 | Free People Shoes | Free People Chelsea Boots (Brooks Boot) | Color: Black/Gray | Size: 9 Brand New, Never Worn Brooks Boots From Free People 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 |
 | Free People Shoes | Free People Chelsea Boot: Textile Atlas Boot | Color: Black/Cream | Size: 7 Patten Leather Heel And Toe Box With Sherpa Textile Design. Comfortable! Euro Size 37.5, Us Shoe Size 7 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 |
 | Burberry Shoes | Burberry Chelsea Boot | Color: Black | Size: 10 Burberry Chelsea Boot Black Leather more | go to store |
 | Zara Shoes | Black Zara Chelsea Boots Size: 40 | Color: Black | Size: 40 Black Zara Chelsea Boots Size: 40 Worn Twice-No Box more | go to store |
 | Classically Cool Pointed Toe Leather Ankle Boots Features A Pull-On Style With V-Cutouts At Both Sides And A Stacked Heel. Features: * Buttery Soft Suede Leather * Pointed Toes * Leather Lining * Cushioned Leather Insole * Imported Measurements (Based... more | go to store |
 | Coach Shoes | Coach Bowery Beaded Chain Chelsea Boot Size 7b | Color: Brown | Size: 7 Coach Bowery Beaded Chain Chelsea Boot. Soft Pointed Toe And Is Finished With A Rugged Stitched Welt. Size: 7b Color: Walnut Style: C0723 Toe Style: Pointy Toe, Closed Toe 1 1/4" Heel Pull-On Style With Elastic Gore Insets Leather Upper/Synthetic... more | go to store |
 | Size 7 Is Sold Out On The J.Crew Website! I Bought These Online Final Sale And They Did Not Work Out For Me. Never Worn - New In Box. Selling To Recoup Most Of What I Paid. Love That They’re A Pair Of Solid, Sleekly Designed Chelsea Boots That Are Not... more | go to store |
 | Free People Shoes | Free People Brooks Chelsea Boots | Color: Gray | Size: Various *New Free People Brooks Chelsea Boots A Contemporary Spin On The Classic Chelsea Style, These Timeless Ankle-Covering Boots Feature A Chunky Sole For An Exaggerated Look. A Super-Chunky Lug Sole Offers An Exaggerated Take On The Trending Utility Look... more | go to store |
 | Free People Shoes | Free People Vance Double Tan Chelsea Boot | Color: Tan | Size: 8 These Free People Vance Double Tan Chelsea Boot Are In Nwot Condition And Oh So Cute!! Love Them But They Are Too Big For Me- Size 38 Eu- Fits More Like An 8-8.5 I Have A More Narrow 7.5 Foot For Reference Made In Spain Only Worn To Try On Heel Height:... more | go to store |
 | Brand New! Size 10 A Super-Chunky Lug Sole Offers An Exaggerated Take On The Trending Utility Look For A Chelsea Boot Updated With An Elongated Shaft. 1 3/4" Heel; 1" Platform 9" Shaft; 11 1/2"-13" Calf Y2k Chunky Boot, Y2k, Vintage Boots New To... more | go to store |
 | - Almond Toe & Tampered - 1 3/4” Heel Height - Euc - Runs 1/2 Small [ 5 ] 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 Ainsley Chelsea Boot | Tan | Color: Tan | Size: 7.5 Madewell Ainsley Chelsea Boot Crafted From Buttery Leather This Updated Chelsea Boot Has A Pared Down Look Thanks To Sleek Convered Insets. Pointed Toe Minor Creasing, Otheriwse In Great Condition Size-7.5 Heel Height- 2in Color- Tan more | go to store |
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