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J. Crew Shoes | J.Crew Chelsea Boots Black Leather Ankle Heel Classic 9 $250 | Color: Black | Size: 9

J. Crew Shoes | J.Crew Chelsea Boots Black Leather Ankle Heel Classic 9 $250 | Color: Black | Size: 9

J.Crew Chelsea Boots Black Leather Ankle Heel Classic 9 $250. Excellent Condition Minimal Wear Size 9 Original Box Included Wardrobe Staple Style Similar To Saint Laurent Ysl Wyatt Boots more

$165.00

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Tory Burch Shoes | New! Tory Burch Medallion Chelsea Suede Ankle Boots Brown 8.5 M Dd330 143638 | Color: Black/Brown | Size: 8.5

Tory Burch Shoes | New! Tory Burch Medallion Chelsea Suede Ankle Boots Brown 8.5 M Dd330 143638 | Color: Black/Brown | Size: 8.5

New! Tory Burch Medallion Chelsea Brown Ankle Boots Size 8.5 M Dd330 Msrp $450 New Without Box- Never Worn-Guaranteed Authenticity Medallion-Plaque Chelsea Ankle Boots From Tory Burch Featuring Suede Upper, Gold-Tone Logo Plaque, Square Pointed Toe,... more

$210.00

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Best Seller
Madewell Shoes | Madewell Leather Ivy Chelsea Ankle Boots. Lug Sole. Light Chestnut Brown. Size 7 | Color: Brown/Tan | Size: 7

Madewell Shoes | Madewell Leather Ivy Chelsea Ankle Boots. Lug Sole. Light Chestnut Brown. Size 7 | Color: Brown/Tan | Size: 7

Gorgeous Madewell Chelsea Ankle Boots. A Beautiful Light Chestnut Color. Lug Soles For Fall, Winter And Spring Weather. Soft Pebbled Leather. Pull-On With Elastic.Size 7. Wore A Couple Of Times, So Leather Creased A Little. They Are Extremely... more

$68.00

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Free People Shoes | Free People Arlo Santa Fe Croc Embossed Chelsea Ankle Boots Tan | Color: Brown/Tan | Size: 7.5

Free People Shoes | Free People Arlo Santa Fe Croc Embossed Chelsea Ankle Boots Tan | Color: Brown/Tan | Size: 7.5

Free People Arlo Santa Fe Croc Embossed Chelsea Ankle Boots Tan Size 37. Fit Close To A Larger Size 7.5 Has A Small Scuff Along Right Shoe On Front. Minimal, However Excellent Pre-Owned Condition Otherwise True To Size* Amp Up Your Style In Thie Arlo... more

$56.00

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Madewell Shoes | Madewell Sonia Leather Snakeskin Low Chelsea Ankle Boots Booties | Color: Black/Gray | Size: 7

Madewell Shoes | Madewell Sonia Leather Snakeskin Low Chelsea Ankle Boots Booties | Color: Black/Gray | Size: 7

Madewell Sonia Leather Snakeskin Low Chelsea Ankle Boots Booties - Excellent Condition - Size 7 - Pointed Toe - Pull On, Elastic Goring - Leather Upper And Lining - Low Block Heel - Minimal Wear I Love Offers And Bundles! Quick Shipping And New Items... more

$65.00

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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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Free People Shoes | Free People James Leather Chelsea Ankle Boots Size 39.5 Us 9.5 New In Box | Color: Cream/White | Size: 9.5

Free People Shoes | Free People James Leather Chelsea Ankle Boots Size 39.5 Us 9.5 New In Box | Color: Cream/White | Size: 9.5

Free People James Leather Chelsea Ankle Boots White Size 39.5 Equivalent To Us 9.5 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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J. Crew Shoes | J Crew Chelsea Boot Ankle Brown Size 10 | Color: Brown | Size: 10

J. Crew Shoes | J Crew Chelsea Boot Ankle Brown Size 10 | Color: Brown | Size: 10

J Crew Chelsea Brown Leather Booties Size 10. It Is Comfortable. Soft Leather Pet/Smoke Free Home. Please See Pictures For More Details. more

$58.00

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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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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 Cleary Chelsea Ankle Boot | Color: Black | Size: 11

Madewell Shoes | Madewell Cleary Chelsea Ankle Boot | Color: Black | Size: 11

Madewell Cleary Chelsea Boot 7/8" Heel. Leather Upper. Pigskin Collar. Rubber Sole. Some Abrasions/Wear To Uppers And Wear To Soles, Otherwise Very Good Preowned Condition. more

$100.00

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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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Anthropologie Shoes | Anthropologie Stompy Chelsea Ankle Pull On Brown Leather Boots Size 37/Us6.5-7 | Color: Brown | Size: 6.5

Anthropologie Shoes | Anthropologie Stompy Chelsea Ankle Pull On Brown Leather Boots Size 37/Us6.5-7 | Color: Brown | Size: 6.5

Very Good Pre-Owned Condition more

$54.00

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Coach Shoes | Coach Mens Chelsea Boots Ankle Suede Pull-On Round Toe Leather Insole Brown 8.5d | Color: Brown | Size: 8.5

Coach Shoes | Coach Mens Chelsea Boots Ankle Suede Pull-On Round Toe Leather Insole Brown 8.5d | Color: Brown | Size: 8.5

Coach Mens Chelsea Boots Ankle Suede Pull-On Round Toe Leather Insole Brown 8.5d Pull On Round Toe Features A Comfortable Crepe Sole Ribbed Ankle Gores Pull Tab For On-And-Off Ease. Style No. G2290 Suede Upper Leather Lining And Footbed Rubber Outsole... more

$69.00

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Free People Shoes | Free People Atlas Suede Chelsea Ankle Boot Sz 36/Us 6 | Color: Brown | Size: 6

Free People Shoes | Free People Atlas Suede Chelsea Ankle Boot Sz 36/Us 6 | Color: Brown | Size: 6

Free People Atlas Suede Chelsea Ankle Boot Sz 36/Us 6 Pieced Leopard Printed Leather Pull-On Bootie Elasticized Insets Scalloped Trim And Stud Details Cushioned Footbed 5 1/2" Shaft Leather Upper/Lining. Manmade Outsole. New Without Box, Never Worn,... more

$134.00

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Anthropologie Shoes | Anthropologie ~Stompy Chelsea Ankle Pull On Brown Leather Boots ~ 39/Us 7.5-8 | Color: Brown | Size: 8

Anthropologie Shoes | Anthropologie ~Stompy Chelsea Ankle Pull On Brown Leather Boots ~ 39/Us 7.5-8 | Color: Brown | Size: 8

In Good Shape Size 39 more

$55.00

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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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Madewell Shoes | Madewell Ankle Boots Chelsea Booties Snake Skin Print Embossed Leather Size 9 | Color: Brown/Cream | Size: 9

Madewell Shoes | Madewell Ankle Boots Chelsea Booties Snake Skin Print Embossed Leather Size 9 | Color: Brown/Cream | Size: 9

Madewell Ankle Boots Chelsea Booties Snake Skin Print Embossed Leather Size 9.Good Condition more

$36.00

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Madewell Shoes | Madewell Grayson Chelsea Ankle Boots In Black Leather 8.5 | Color: Black/Brown | Size: 8.5

Madewell Shoes | Madewell Grayson Chelsea Ankle Boots In Black Leather 8.5 | Color: Black/Brown | Size: 8.5

Madewell Grayson Chelsea Ankle Boots In Black Leather 8.5 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... more

$88.00

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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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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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Madewell Shoes | Madewell Size 9 Brynn Ankle Heeled Chelsea Boot With Velvet Trim | Color: Black | Size: 9

Madewell Shoes | Madewell Size 9 Brynn Ankle Heeled Chelsea Boot With Velvet Trim | Color: Black | Size: 9

Madewell Size 9 Brynn Ankle Heeled Chelsea Boot With Velvet Trim 1 1/2” Heel 4 1/2” Shaft Height Leather, Suede Upper Man-Made Sole Style # Mb834 Slight Scuffing On Rim Of Front Toes But Not Noticeable When Wearing more

$32.00

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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 Lonny Ankle Boots Booties Black Leather Chelsea 9.5 | Color: Black | Size: 9.5

Madewell Shoes | Madewell Lonny Ankle Boots Booties Black Leather Chelsea 9.5 | Color: Black | Size: 9.5

Madewell Lonny Ankle Boots Booties Black Leather Chelsea. Heeled 3.5” Stacked Wood Chunky Heels. Elastic Goring On The Sides With A Decorative Strap. more

$60.00

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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 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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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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Michael Kors Shoes | Michael Kors Shaw Flat Suede Bootie Ankle Boots Chelsea Tan Camel 9 | Color: Cream/Tan | Size: 9

Michael Kors Shoes | Michael Kors Shaw Flat Suede Bootie Ankle Boots Chelsea Tan Camel 9 | Color: Cream/Tan | Size: 9

Michael Kors Shaw Flat Suede Bootie Ankle Boots Chelsea Tan Camel Size 9 A Sharply Bootie Fashioned From Smooth ,Burnished Black Leather Dials Up The Chic Appeal Of Your Daily Style, While Logo-Etched Hardware Flashes At The Heel For A Signature... more

$20.00

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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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Madewell Shoes | Madewell Regan Black Leather Chelsea Pull On Ankle Boot - Size 9.5 Cloud J8307 | Color: Black | Size: 9.5

Madewell Shoes | Madewell Regan Black Leather Chelsea Pull On Ankle Boot - Size 9.5 Cloud J8307 | Color: Black | Size: 9.5

Madewell Regan Black Leather Chelsea Pull On Ankle Boot Size 9.5 Heel = 2.75". Style J8307 Modern Style Chelsea Boot In Black Leather, Looks Great With Anything! Comfortable Block Heel And Easy Pull On Style. Msrp $178. Gently Used Condition With Minor... more

$110.00

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Tory Burch Shoes | New! Tory Burch Medallion-Plaque 35mm Chelsea Ankle Boots Size 8.5 M Dd386 | Color: Black | Size: 8.5

Tory Burch Shoes | New! Tory Burch Medallion-Plaque 35mm Chelsea Ankle Boots Size 8.5 M Dd386 | Color: Black | Size: 8.5

New! Tory Burch Medallion-Plaque 35mm Chelsea Ankle Boots Size 8.5 M Dd386 Msrp $450 New Without Box- Never Worn-Guaranteed Authenticity Medallion-Plaque 35mm Ankle Boots From Tory Burch Featuring Black, Calf Leather, Gold-Tone Logo Plaque, Pointed... more

$190.00

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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 James Leather Chelsea Ankle Boots Size 41 Us 11 New In Box | Color: Cream/White | Size: 11

Free People Shoes | Free People James Leather Chelsea Ankle Boots Size 41 Us 11 New In Box | Color: Cream/White | Size: 11

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

$100.00

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Madewell Shoes | Madewell Sonia Chelsea Ankle Bootie Boot Leather Snakeskin 11 M3463 | Color: Black/Brown | Size: 11

Madewell Shoes | Madewell Sonia Chelsea Ankle Bootie Boot Leather Snakeskin 11 M3463 | Color: Black/Brown | Size: 11

Good Preowned Condition. Light Wear As Shown In Photos. 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 Elastic Gore Insets Cushioned Footbed... more

$68.00

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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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Free People Shoes | Free People Atlas Chelsea Ankle Boot Black Suade Eu 40 | Color: Black | Size: 40eu

Free People Shoes | Free People Atlas Chelsea Ankle Boot Black Suade Eu 40 | Color: Black | Size: 40eu

Free People Atlas Chelsea Ankle Boot Eu 40 In My Opinion, They Fit Like 9.5 Us Good Used Condition Minor Signs Of Wear, Wear On Bottom, Light Scuff On Side Pictured. Free People Logo Worn Off On Inside And Some Glitter Inside I Couldn't Get Out Brass... more

$47.00

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