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J. Crew Shoes | Black Madewell Chunky Chelsea Ankle Boot. Size 8.5. | Color: Black | Size: 8.5

J. Crew Shoes | Black Madewell Chunky Chelsea Ankle Boot. Size 8.5. | Color: Black | Size: 8.5

Black Madewell Chunky Chelsea Ankle Boot. Size 8.5. Never Worn. New In Box. more

$150.00

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Michael Kors Shoes | Michael Kors Leather Sole Chelsea Ankle Boots 8 Brown Pull On Chunky Heel | Color: Brown | Size: 8

Michael Kors Shoes | Michael Kors Leather Sole Chelsea Ankle Boots 8 Brown Pull On Chunky Heel | Color: Brown | Size: 8

Michael Kors Leather Sole Chelsea Ankle Boots 8m Brown Pull On Chunky Heel Very Good Used Condition - Wear On Soles And Light Wear At Top Edge Of Elastic Sections (See Pictures) more

$40.00

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Best Seller
American Eagle Outfitters Shoes | American Eagle Black Cow Suede Leather Chelsea Ankle Boots Size 10 Block Heels | Color: Black | Size: 10

American Eagle Outfitters Shoes | American Eagle Black Cow Suede Leather Chelsea Ankle Boots Size 10 Block Heels | Color: Black | Size: 10

This Is A Timeless Boot That Has A Minimalist Modern Look For Any Outfit more

$30.00

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Madewell Shoes | Madewell Carina Ankle Chelsea Boot In English Saddle Size 6 | Color: Tan | Size: 6

Madewell Shoes | Madewell Carina Ankle Chelsea Boot In English Saddle Size 6 | Color: Tan | Size: 6

Madewell Carina Ankle Chelsea Boot In English Saddle Woman's Size 6 With A Rounded Toe And Stacked Heel That's Perfect For Walking Around In All Day, This Chelsea Boot Is A Wear-Everywhere Style Standby. Preowned Good Condition. Please See Pictures For... more

$29.00

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Kate Spade Shoes | Kate Spade Leah Leopard Print Chelsea Ankle Boots | Color: Brown/Tan | Size: 8.5

Kate Spade Shoes | Kate Spade Leah Leopard Print Chelsea Ankle Boots | Color: Brown/Tan | Size: 8.5

- Condition 7.5/10, Minimal Wear, Main Flaw Is Rubbing On Front Of Toe, (Not Too Noticeable, Look At Photos For Flaws) - Kate Spade Leah Calf Hair Leopard Print Ankle Boots, Features Chelsea / Stretch Panels On The Side, A Block Heal, Kate Spade Emblem... more

$70.00

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Free People Shoes | Free People Essential Chelsea Ankle Boot Deep River Teal Leather Eu Size 38 Nwot | Color: Blue/Green | Size: 38eu

Free People Shoes | Free People Essential Chelsea Ankle Boot Deep River Teal Leather Eu Size 38 Nwot | Color: Blue/Green | Size: 38eu

Nwot Free People Essential Chelsea Ankle Boot Deep River Teal Leather * Size: Eu Size 38 (Us Size 7.5 Per Free People) * Color: Deep River (Teal Green/Blue) * Faded Leather Uppers * Back Zipper Closure * Elastic Side Gore Panels * Cushioned Insoles *... more

$125.00

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Madewell Shoes | Madewell Bryce Chelsea Camel Brown Suede Ankle Booties Boots | Color: Brown | Size: 8.5

Madewell Shoes | Madewell Bryce Chelsea Camel Brown Suede Ankle Booties Boots | Color: Brown | Size: 8.5

Madewell Bryce Chelsea Camel Brown Suede Ankle Booties Boots Size 8.5 Good Preowned Condition 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 Right At The Ankle. -... more

$39.00

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J. Crew Shoes | Black Chelsea Ankle Boots 6.5 | Color: Black | Size: 6.5

J. Crew Shoes | Black Chelsea Ankle Boots 6.5 | Color: Black | Size: 6.5

These Are Black Chelsea Ankle Boots That I Wore So Religiously That I Bought Two Pairs When They Were On Sale As Back Up. I Don’t Need Two Extra Pairs Tho So I’m Selling These Now. Have Hardly Been Worn But Were In Storage For A While And They Deserve... more

$60.00

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Free People Shoes | Free People Castillo Chelsea Boots Ankle Size 38 | Color: Brown/Red | Size: 8

Free People Shoes | Free People Castillo Chelsea Boots Ankle Size 38 | Color: Brown/Red | Size: 8

Free People Castillo Chelsea Boot - Size 38 Eu/ Us Women’s 8. Fits Size 8.5 Snug. Purchased From Free People Directly Years Ago And Held Onto Them Because They’re So Cute But Unfortunately A Little Too Small For Me. Made With Real Patent Leather And... more

$36.00

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Kate Spade Shoes | Kate Spade Garden Gray/ Truffle Suede Scalloped Chelsea Ankle Boots | Color: Black/Gray | Size: 7

Kate Spade Shoes | Kate Spade Garden Gray/ Truffle Suede Scalloped Chelsea Ankle Boots | Color: Black/Gray | Size: 7

Kate Spade Garden Gray/ Truffle Suede Scalloped Chelsea Ankle Boots Beautiful Graphite Dark Truffle Gray Slip On Style With Side Gore Panels Feminine Scallop Details Sweet Back Heel Bow Round Toe Cushioned Insole Leather Sole 3” Block Heel Made In... more

$70.00

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Free People Shoes | Free People James Tan Brown Leather Chunky James Chelsea Ankle Boots New Size 41 | Color: Brown/Tan | Size: 11

Free People Shoes | Free People James Tan Brown Leather Chunky James Chelsea Ankle Boots New Size 41 | Color: Brown/Tan | Size: 11

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

$120.00

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Gucci Shoes | Gucci Cordovan Lux Pointed Toe Side Buckle Chelsea Ankle Boots White Size 37 New | Color: White | Size: 37eu

Gucci Shoes | Gucci Cordovan Lux Pointed Toe Side Buckle Chelsea Ankle Boots White Size 37 New | Color: White | Size: 37eu

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

$489.00

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Free People Shoes | Free People Arlo Santa Fe Ankle Chelsea Boots Black Crocodile Snake Size 7 | Color: Black | Size: 7

Free People Shoes | Free People Arlo Santa Fe Ankle Chelsea Boots Black Crocodile Snake Size 7 | Color: Black | Size: 7

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

$80.00

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

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

Madewell Sonia Leather Snakeskin Chelsea Boots. Size 7.5 Light Wear Ships Without Original Shoe Box. more

$38.00

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Kate Spade Shoes | Kate Spade Sedgewick Domina Leopard Print Chelsea Ankle Rain Boots | Color: Black/Brown | Size: 6/7 Eu 37

Kate Spade Shoes | Kate Spade Sedgewick Domina Leopard Print Chelsea Ankle Rain Boots | Color: Black/Brown | Size: 6/7 Eu 37

Kate Spade Sedgewick Domina Leopard Print Chelsea Ankle Rain Boots. Product Details Material Rubber With Elastic And Rubber Heel Features 1.2" Heel Pull On Back Tab Water-Resistant Size Is A Ladies 6/7 Eu 37 Great Preowned Condition With Only Some... more

$21.00

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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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Madewell Shoes | Madewell Snakeskin Chelsea Leather Ankle Boot | Color: Brown | Size: 8

Madewell Shoes | Madewell Snakeskin Chelsea Leather Ankle Boot | Color: Brown | Size: 8

New Madewell Snakeskin Print Chelsea Ankle Boot. New Without Box! - Women Size 8 - Fast Shipping! more

$75.00

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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

$35.00

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Free People Shoes | Free People Gold Croc Embossed Beau Western Chelsea Boot Ankle Booties | Color: Gold/Red | Size: Various

Free People Shoes | Free People Gold Croc Embossed Beau Western Chelsea Boot Ankle Booties | Color: Gold/Red | Size: Various

So Stunning And Effortlessly Eye-Catching, These Cool Ankle Boots Are Featured In A Western-Style Silhouette And Buttery Soft Leather With Elastic Side Panels, A Minimal Wooden Block Heel, And Bold Pointy Toe. Pull On Style Pull Tabs At Heel Cushioned... more

$160.00

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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 - The Grayson Brogue Tan Suede Chelsea Western Ankle Boot Size 8.5 | Color: Brown/Tan | Size: 8.5

Madewell Shoes | Madewell - The Grayson Brogue Tan Suede Chelsea Western Ankle Boot Size 8.5 | Color: Brown/Tan | Size: 8.5

Madewell - The Grayson Brogue Chelsea Tan Suede Ankle Boot Size 8.5 Excellent Condition Small Scratches On Bottom Of Boot Size 8.5 Heel Height - 2.5 Western Boot Details Stacked Raw Leather Heels Pointy Toe Pull On Style 3” Shaft Height Suede Upper... more

$89.00

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Free People Shoes | Free People Beau Western Ankle Chelsea Boot Embossed Gold Leather | Color: Black/Gold | Size: Various

Free People Shoes | Free People Beau Western Ankle Chelsea Boot Embossed Gold Leather | Color: Black/Gold | Size: Various

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

$178.00

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Free People Shoes | Free People Atlas Chelsea Puffer Ankle Boots Black Size 10 Us 41 Eu New | Color: Black | Size: 10

Free People Shoes | Free People Atlas Chelsea Puffer Ankle Boots Black Size 10 Us 41 Eu New | Color: Black | Size: 10

Free People Atlas Chelsea Puffer Ankle Boots Black Size 10 Us 41 Eu New Size 10, Women's The Item Is New Without Box. Please See All Pictures As They Are Also Part Of The Description. You Will Receive The Exact Item That You See In The Photos. All... more

$99.00

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Anthropologie Shoes | Hoss Intropia - Tan Suede Ankle Chelsea Boots, 9 | Color: Brown/Tan | Size: 9

Anthropologie Shoes | Hoss Intropia - Tan Suede Ankle Chelsea Boots, 9 | Color: Brown/Tan | Size: 9

Hoss Intropia Tan Suede Ankle Boots With Back Zip Detail And Stacked Wooden Heel Pre-Owned - Fair Condition, Denim Dye Spot Transfers At The Edges On Top, Can Be Professionally Cleaned For Additional Cost, Added Vibram Sole, See Images, Ask Questions,... more

$199.00

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J. Crew Shoes | J Crew Olive Green Pull On Chelsea Rain Boot Ankle 7 | Color: Green | Size: 7

J. Crew Shoes | J Crew Olive Green Pull On Chelsea Rain Boot Ankle 7 | Color: Green | Size: 7

J Crew Olive Green Pull On Chelsea Rain Boot Ankle 7 Preowned Has Some Wear See Photos Shoe3 more

$32.00

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Free People Shoes | Free People Atlas Black Puffer Chelsea Ankle Boots | Color: Black | Size: 8.5

Free People Shoes | Free People Atlas Black Puffer Chelsea Ankle Boots | Color: Black | Size: 8.5

Please Read Description Above About This Brand New Puffer Boot! more

$112.00

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Free People Shoes | Free People Atlas Chelsea Black Leather Suede Ankle Boots Minimalist Grunge | Color: Black | Size: 40eu

Free People Shoes | Free People Atlas Chelsea Black Leather Suede Ankle Boots Minimalist Grunge | Color: Black | Size: 40eu

Free People Atlas Chelsea Black Leather Suede Ankle Boots Minimalist Grunge Size 40 Gently Used more

$65.00

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Madewell Shoes | Madewell Sonia Ankle Low Chelsea Boots Leather | Color: Brown/Tan | Size: Various

Madewell Shoes | Madewell Sonia Ankle Low Chelsea Boots Leather | Color: Brown/Tan | Size: Various

Madewell Sonia Ankle Low Chelsea Boots Brand New In Box Retail $188 Color: Tan And Black With Snakeskin Pattern / "Heather Natural Multi" Description: An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A... more

$110.00

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Madewell Shoes | Madewell Sonia Low Snakeskin Chelsea Ankle Boots Size 5.5 | Color: Black/Cream | Size: 5.5

Madewell Shoes | Madewell Sonia Low Snakeskin Chelsea Ankle Boots Size 5.5 | Color: Black/Cream | Size: 5.5

Madewell Sonia Low Snakeskin Chelsea Ankle Boots Size 5.5 - Snake Print - Leather Uppers And Lining Flaws: Small Scratch On Front Of Ankle (See Close Up Photo). Offers Welcome! Bundle Items In My Closet For The Best Deal! more

$25.00

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Kate Spade Shoes | Mocha Chelsea Ankle Boots | Color: Brown | Size: 8

Kate Spade Shoes | Mocha Chelsea Ankle Boots | Color: Brown | Size: 8

Kate Spade Mocha Chelsea Boots. Size 8. Excellent Condition more

$40.00

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Madewell Shoes | Madewell Black Rubber Chelsea Rain Waterproof Ankle Boots Size 7 | Color: Black | Size: 7

Madewell Shoes | Madewell Black Rubber Chelsea Rain Waterproof Ankle Boots Size 7 | Color: Black | Size: 7

Madewell Black Chelsea Rain Waterproof Ankle Boots Size 7 Smoke Free Home Bundle For A Discount more

$54.00

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Madewell Shoes | Madewell Size 9 The Grayson Black Leather Ankle Chelsea Boot J8293 | Color: Black | Size: 9

Madewell Shoes | Madewell Size 9 The Grayson Black Leather Ankle Chelsea Boot J8293 | Color: Black | Size: 9

Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toeand Cut Them Low On The Ankle To Make Your Legs Look Even Longer. A Pull-On Style For In-Between Weather (Just Add Cropped Jeans). Cushiness Alert: We've Added An... more

$128.00

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Madewell Shoes | Madewell Spencer Taupe Chelsea Slip On Leather Ankle Boots Size 8.5 | Color: Tan | Size: 8.5

Madewell Shoes | Madewell Spencer Taupe Chelsea Slip On Leather Ankle Boots Size 8.5 | Color: Tan | Size: 8.5

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

$50.00

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Free People Shoes | Free People Western Ankle Leather Chelsea Boots Size 7.5=8.5 Retail $178 | Color: Black | Size: 7.5

Free People Shoes | Free People Western Ankle Leather Chelsea Boots Size 7.5=8.5 Retail $178 | Color: Black | Size: 7.5

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

$75.00

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Gucci Shoes | Gucci Boots Mens Chelsea Ankle Black Leather Logo Hardware Sz 11 11.5 | Color: Black | Size: 11.5

Gucci Shoes | Gucci Boots Mens Chelsea Ankle Black Leather Logo Hardware Sz 11 11.5 | Color: Black | Size: 11.5

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

$599.00

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Free People Shoes | Free People Brooks Lug Sole Chelsea Boot Tall Ankle Leather Shoes Black Suede | Color: Black | Size: 8

Free People Shoes | Free People Brooks Lug Sole Chelsea Boot Tall Ankle Leather Shoes Black Suede | Color: Black | Size: 8

Free People Brooks Lug Sole Chelsea Boot Tall Ankle Leather Shoes Black Suede Size 38/Us 8 Nwob New Without Box. Store Display Model. Minor Wear From Being Tried On In A Retail Environment. Please See Photos. Never Worn Outside. Smoke Free Home. Fast... more

$90.00

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