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Madewell Shoes | Madewell The Grayson Chelsea Ankle Boots Black Leather Pointed Toe Size 7 | Color: Black | Size: 7

Madewell Shoes | Madewell The Grayson Chelsea Ankle Boots Black Leather Pointed Toe Size 7 | Color: Black | Size: 7

Gently Used Condition. Some Scrapes. See Photos. more

$35.00

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J. Crew Shoes | J.Crew Black Ankle Rain Boots Chelsea Size 8 | Color: Black | Size: 8

J. Crew Shoes | J.Crew Black Ankle Rain Boots Chelsea Size 8 | Color: Black | Size: 8

J.Crew Black Chelsea Boots Size 8 Great For Winter, Rainy Weather, Cold Season, Puddle Jumping, Gardening, Etc more

$35.00

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Best Seller
Free People Shoes | Free People Huntley High Ankle Chelsea Boots In Bone | Color: Cream/White | Size: 8

Free People Shoes | Free People Huntley High Ankle Chelsea Boots In Bone | Color: Cream/White | Size: 8

Reposhing This Item I Purchased From @Mltldl. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! more

$99.00

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Kate Spade Shoes | Kate Spade Bellamy Suede Tassel Chelsea Ankle Boots In Stone Grey Size 9.5 Euc | Color: Cream/Gray | Size: 9.5

Kate Spade Shoes | Kate Spade Bellamy Suede Tassel Chelsea Ankle Boots In Stone Grey Size 9.5 Euc | Color: Cream/Gray | Size: 9.5

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

$62.00

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Free People Shoes | Free People Textile Atlas Ankle Chelsea Boots In Blue Kilim 40 | Color: Black/Blue | Size: 40eu

Free People Shoes | Free People Textile Atlas Ankle Chelsea Boots In Blue Kilim 40 | Color: Black/Blue | Size: 40eu

Free People Atlas Chelsea Bootie Black Leather Fabric 40 New Without Box Tufts Of Faux Shearling Woven Into A Jacquard Pattern Create Eye-Catching Texture On This Mixed-Media Version Of A Classic Chelsea Boot. Studded Patchwork Look 5 1/2" Shaft... more

$100.00

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Free People Shoes | Free People Atlas Ankle Studded Suede Chelsea Boots Black 9.5 | Color: Black | Size: 39.5eu

Free People Shoes | Free People Atlas Ankle Studded Suede Chelsea Boots Black 9.5 | Color: Black | Size: 39.5eu

Brand - Free People Size - Eu 39.5 / Us 9.5 Excellent Preowned Condition Ankle, Chelsea, Studded Trim, Scalloped Lace Trim, Pull On, Side Stretch, Suede, Leather, Round Toe, Comfortable, Hiking, Causal, Winter, Fall, Combat, Booties more

$85.00

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Coach Shoes | Coach Black Snake Skin Leather Patchwork Chelsea Ankle Boots Booties 8.5 | Color: Black | Size: 8.5

Coach Shoes | Coach Black Snake Skin Leather Patchwork Chelsea Ankle Boots Booties 8.5 | Color: Black | Size: 8.5

Coach Snake Skin And Leather Patchwork Chelsea Ankle Boots Size: 8.5 Black Good Used Condition-Flaws Include Some Scrapes Of Normal Wear And Some Fading On The Suede Otherwise In Good Condition Tags: Fall, Autumn, Western Boots, Boots more

$55.00

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Madewell Shoes | Madewell The Ainsley Chelsea Leather Boot In Black Size 7 Ankle Bootie | Color: Black | Size: 7

Madewell Shoes | Madewell The Ainsley Chelsea Leather Boot In Black Size 7 Ankle Bootie | Color: Black | Size: 7

Madewell The Ainsley Chelsea Leather Boot In Black Size 7 Ankle Booties Have Light Scuffs And Distressing But They’re High Quality/Beautifully Made And Have A Lot Of Life Left. more

$38.00

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Gucci Shoes | Gucci Boots Mens Chelsea Ankle Black Leather Nwt Logo Hardware $900 Sz 9 9.5 | Color: Black | Size: 9

Gucci Shoes | Gucci Boots Mens Chelsea Ankle Black Leather Nwt Logo Hardware $900 Sz 9 9.5 | Color: Black | Size: 9

Stunning! Brand New With Tags, Never Worn. Gucci Boots Mens Chelsea Ankle Black Leather Logo Hardware!! Sz 9 9.5 Fantastic Shoes With Stylish 'Eye' Engraving On The Soles! (See Pics). Absolutely Pristine Condition. Mint. Super Comfortable With A... more

$900.00

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Free People Shoes | Free People Dark Horse Taupe Leather Ankle Chelsea Boots | Color: Black/Tan | Size: 7

Free People Shoes | Free People Dark Horse Taupe Leather Ankle Chelsea Boots | Color: Black/Tan | Size: 7

Excellent Used Condition Retails $198 Please See Pics For Wear more

$89.00

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Burberry Shoes | Brand New Authentic Burberry Tb Monogram Leather Buckle Ankle Chelsea Boot | Color: Black | Size: 44

Burberry Shoes | Brand New Authentic Burberry Tb Monogram Leather Buckle Ankle Chelsea Boot | Color: Black | Size: 44

Perfect Gift For Father’s Day! Introducing The Burberry Luke Tb Monogram Buckle Leather Chelsea Boot In Black Size 44. These Stylish Boots Feature An Almond Toe Shape And Pull-On Closure For Easy Wear. Perfect For Any Occasion, Whether It Be A Party,... more

$625.00

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Free People Shoes | Free People Castillo Chelsea Boots Ankle | Size 37 (6-6.5) | Color: Brown | Size: 6.5

Free People Shoes | Free People Castillo Chelsea Boots Ankle | Size 37 (6-6.5) | Color: Brown | Size: 6.5

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

$89.00

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J. Crew Shoes | J. Crew Chelsea Leather Ankle Boot, Size 9 | Color: Black | Size: 9

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

$40.00

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Free People Shoes | Free People Oxblood Carmel Leather Block Heel Platform Chelsea Ankle Boots 7.5 | Color: Red | Size: 7.5

Free People Shoes | Free People Oxblood Carmel Leather Block Heel Platform Chelsea Ankle Boots 7.5 | Color: Red | Size: 7.5

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

$125.00

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Coach Shoes | Coach Lyden Leather Ankle Chelsea Boots In White Size 10 | Color: Cream/White | Size: 10

Coach Shoes | Coach Lyden Leather Ankle Chelsea Boots In White Size 10 | Color: Cream/White | Size: 10

Worn Less Than 5 Times! Just Hits My Ankle In A Weird Spot, Nothing Wrong With Them. Originally $250 Last Winter. Make An Offer! more

$75.00

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Madewell Shoes | Madewell Sonia Snakeskin Leather Chelsea Ankle Boot Size 7.5 | Color: Black/Brown | Size: 7.5

Madewell Shoes | Madewell Sonia Snakeskin Leather Chelsea Ankle Boot Size 7.5 | Color: Black/Brown | Size: 7.5

Madewell Sonia Snakeskin Leather Chelsea Ankle Boot Size 7.5 Like New Condition - Minor Wear On Balls From Try-Ons And Minor Markings On Insole Of Right Boot From A Sticker That Was Removed. -Almond Toe -Pull-On-Style -Elastic Gore Inset -Cushioned... more

$40.00

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Gucci Shoes | Gucci Mens Boots Leon Ankle Chelsea Logo Back Black Leather Sz 9g 9.5 Us | Color: Black | Size: 9.5

Gucci Shoes | Gucci Mens Boots Leon Ankle Chelsea Logo Back Black Leather Sz 9g 9.5 Us | Color: Black | Size: 9.5

Designer: Gucci Size: Marked As 9 G / Converts To Us 9.5 (Conversion Per Designer's Website) Condition: Authentic And Brand New Style Name / Number: 592861 Dtn50 1000 Material: Leather Upper, Rubber Sole Unique Features: Mens Black Leather Logo Patch... more

$699.00

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Madewell Shoes | Madewell The Spencer Chelsea Leather Ankle Boots | Color: Tan | Size: 9.5

Madewell Shoes | Madewell The Spencer Chelsea Leather Ankle Boots | Color: Tan | Size: 9.5

Madewell 9.5 Spencer Short Chelsea Boot Style C1375 Mink Taupe Tan Color Stacked Heel No Original Box Slight Marks In Leather (See Photos) Excellent Used Condition 1.75" Heel Almond Toe Luxe Quality Stretch On Both Sides Offers Welcome. No Trades. more

$36.00

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Free People Shoes | Free People James Chelsea Ankle Velvet Boots | Color: Black | Size: 37

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

$145.00

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Madewell Shoes | Madewell Ivy Chelsea Leather Black Ankle Boots 8 | Color: Black | Size: 8

Madewell Shoes | Madewell Ivy Chelsea Leather Black Ankle Boots 8 | Color: Black | Size: 8

Madewell The Ivy Chelsea Boot In Leather Madewell Classic Chelsea Boots With A Utilitarian Lug Sole. Made Of Rich Leather, They'll Look Cooler And Cooler The More You Wear 'Em. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On... more

$99.00

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Gucci Shoes | Gucci Marmont Double G Mateless Leather Chelsea Ankle Boots | Color: Black | Size: 10.5

Gucci Shoes | Gucci Marmont Double G Mateless Leather Chelsea Ankle Boots | Color: Black | Size: 10.5

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

$950.00

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Levi's Shoes | Levis Mens Keith Pull On Chelsea Ankle Boots Tan/ Brown Suede Size 13 M Us (Nwt) | Color: Tan | Size: 13

Levi's Shoes | Levis Mens Keith Pull On Chelsea Ankle Boots Tan/ Brown Suede Size 13 M Us (Nwt) | Color: Tan | Size: 13

Complement Your Classic Look With The New Keith Suede Chelsea Boot From Levi’s! These Handsome Chelsea Boots Feature Soft Suede Uppers With Dual Elastic Gore For Easy On And Off And Memory Foam Footbed For Lasting Comfort. more

$50.00

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Madewell Shoes | Madewell Bryce Suede Leather Chelsea Ankle Boots Tan Size 7 | Color: Tan | Size: 7

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

$35.00

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J. Crew Shoes | J Crew Crepe Sole Chelsea Ankle Boots Brown And Black Leather Size 6.5 | Color: Black/Brown | Size: 6.5

J. Crew Shoes | J Crew Crepe Sole Chelsea Ankle Boots Brown And Black Leather Size 6.5 | Color: Black/Brown | Size: 6.5

Some Wear But In Good Condition. more

$45.00

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Zara Shoes | Leather Chelsea Ankle Boots Sz 9 Or Eu 42 | Color: Black | Size: 9

Zara Shoes | Leather Chelsea Ankle Boots Sz 9 Or Eu 42 | Color: Black | Size: 9

Leather Chelsea Ankle Boots Sz 9 Or Eu 42 #53- 896 more

$79.00

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J. Crew Shoes | J Crew Chelsea Ankle Boot In Evergreen Size 5 | Color: Green | Size: 5

J. Crew Shoes | J Crew Chelsea Ankle Boot In Evergreen Size 5 | Color: Green | Size: 5

Slightly Worn J Crew Ankle Boot. True To Size. Rubber With Elastic Stretch Around Ankle. Low Heel. more

$18.00

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J. Crew Shoes | J. Crew Black Chelsea Ankle Boot - Size 7.5 | Color: Black | Size: 7.5

J. Crew Shoes | J. Crew Black Chelsea Ankle Boot - Size 7.5 | Color: Black | Size: 7.5

J. Crew Black Chelsea Ankle Boot - Size 7.5 With Shoe Box more

$125.00

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Tory Burch Shoes | $500 Tory Burch Medallion Chelsea Ankle Boot Suede River Rock 6.5 (Me12) | Color: Brown | Size: 6.5

Tory Burch Shoes | $500 Tory Burch Medallion Chelsea Ankle Boot Suede River Rock 6.5 (Me12) | Color: Brown | Size: 6.5

Floor Model And Tried On Excellent - Please See Pictures!! The Quintessential Fall Shoe. Our Chelsea Boot Is An Ultra-Versatile Silhouette Crafted From Soft Suede And Set On A Low Stacked Heel. Elastic Panels And A Back Pull Tab Ensure Ease And... more

$200.00

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Free People Shoes | Free People James Chelsea Ankle Boots In White New In Box | Color: Black/White | Size: 8

Free People Shoes | Free People James Chelsea Ankle Boots In White New In Box | Color: Black/White | Size: 8

Reposhing This Item I Purchased From @Sydney_coop21. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! more

$50.00

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J. Crew Shoes | ! J.Crew $238 Chelsea Leather Ankle Boots E0824 | Color: Black | Size: Various

J. Crew Shoes | ! J.Crew $238 Chelsea Leather Ankle Boots E0824 | Color: Black | Size: Various

Jcrew $238 Chelsea Leather Ankle Boots Black Shoes E0824 Just Try To Complete Your Fall And Winter Outfits Without Comfortable And Stylish Boots. Style, Comfort, And Flair -- What More Could You Want In A Boot? Famous For Their Trendy Yet Functional... more

$46.00

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Free People Shoes | Free People Chelsea Heeled Bone White Ankle Boots Sz 39 Nwob, Some Try On Scuffs | Color: Cream/White | Size: 39eu

Free People Shoes | Free People Chelsea Heeled Bone White Ankle Boots Sz 39 Nwob, Some Try On Scuffs | Color: Cream/White | Size: 39eu

Boho Urban Chic In These Gorgeous Free People Chelsea Boots Free People Recommends Sizing Up 1/2 Size Nwob Some Minor Try On Scuffing No Other Imperfections See Pics For Item Details more

$64.00

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Free People Shoes | Free People James Leather Chelsea Ankle Boots Size 36 Us 6 New In Box | Color: Cream/White | Size: 6

Free People Shoes | Free People James Leather Chelsea Ankle Boots Size 36 Us 6 New In Box | Color: Cream/White | Size: 6

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

$100.00

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Burberry Shoes | Burberry Men’s Chelsea Ankle Boots Dark Brown 45 | Color: Brown | Size: 45

Burberry Shoes | Burberry Men’s Chelsea Ankle Boots Dark Brown 45 | Color: Brown | Size: 45

100% Authentic Guarantee Retail $775 New With Box ( No Dust Bag ) Store Display Slight Signs Of Store Trying On Outsoles Color: Dark Brown Eu Size 45 Insole Approx 12.25" Width Approx 4" Please See Pictures more

$475.00

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Anthropologie Shoes | Anthropology Chelsea Platform Ankle High Boots | Color: Orange | Size: 9

Anthropologie Shoes | Anthropology Chelsea Platform Ankle High Boots | Color: Orange | Size: 9

Anthropology Chelsea Platform Ankle High Boots. Very Comfortable And Trendy. Previously Loved But In Great Condition. It Is A Peach Color more

$89.00

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Madewell Shoes | Madewell "Ainsley Chelsea" In Spotted Calf Hair Ankle Boot Size 6 | Color: Black | Size: 6

Madewell Shoes | Madewell "Ainsley Chelsea" In Spotted Calf Hair Ankle Boot Size 6 | Color: Black | Size: 6

Madewell "Ainsley Chelsea" In Spotted Calf Hair Ankle Boot Size 6 1 3/16" Heel Calf Hair Upper Man-Made Sole more

$25.00

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Free People Shoes | Black Free People Ankle Chelsea Boot | Color: Black | Size: 8

Free People Shoes | Black Free People Ankle Chelsea Boot | Color: Black | Size: 8

There Are A Euro Size 41 (Us 8) Free People Cowboy/ Chelsea Boot Style Stretchy On The Side Like A Chelsea Boot Small Heel more

$45.00

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J. Crew Shoes | J. Crew Black Leather Pointed Toe Ankle Cowboy Booties Chelsea Boots 9 | Color: Black | Size: 9

J. Crew Shoes | J. Crew Black Leather Pointed Toe Ankle Cowboy Booties Chelsea Boots 9 | Color: Black | Size: 9

J. Crew Black Leather Slip-On Style Ankle Booties With Elastic Panels For Easy On/Off. Modern Pointed Toe With A Small Block Heel. Tag Size 9 Preowned. Some Wear On Heel Block And Some Minor Creasing Of Leather. Toe Leather Is Nicked And Markings On... more

$36.00

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Free People Shoes | Free People James Leather Chelsea Ankle Boots Size 38.5 Us 8.5 New In Box | Color: Cream/White | Size: 8.5

Free People Shoes | Free People James Leather Chelsea Ankle Boots Size 38.5 Us 8.5 New In Box | Color: Cream/White | Size: 8.5

Reposhing This Item I Purchased From @Desertsunstyle. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! more

$90.00

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Gucci Shoes | Gucci Horsebit Chain Leather Chelsea Black Ankle Boot 38.5 | Color: Black | Size: 38.5eu

Gucci Shoes | Gucci Horsebit Chain Leather Chelsea Black Ankle Boot 38.5 | Color: Black | Size: 38.5eu

New In Box With Dustbags And Cards 100% Authentic Eu 38.5 // Us 8.5 Retails $1,275 Style 670393 17k10 1000 A Classic Shape Is Reimagined With Distinctive House Codes. Crafted From Black Leather, This Pair Of Chelsea Boots Are Enriched By The Horsebit... more

$855.00

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Madewell Shoes | Madewell Ankle Chelsea Boots Size 7 In Black Leather | Color: Black | Size: 7

Madewell Shoes | Madewell Ankle Chelsea Boots Size 7 In Black Leather | Color: Black | Size: 7

Beautiful Black Leather Ankle Boots From Madewell In Size 7. These Ankle Boots Go With Everything! Versatile And Comfortable, Easy To Slip On And Wear All Day. They’re High Quality Basics That You Can Keep Forever And They’ll Never Go Out Of Style.... more

$36.00

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More information about Men's Shoes

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