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Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

Reposhing This Item I Purchased From @Cooldudz. Used 1x For A Wedding Rehearsal And Now That I Am Working From Home I Don’t Wear/Need Heels Anymore. Loved Them, Fit Well And Very Stylish. more

$50.00

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Madewell Shoes | Madewell The Grayson Chelsea Boot Black Leather Pointed Toe Ankle Boots Size 10 | Color: Black/Brown | Size: 10

Madewell Shoes | Madewell The Grayson Chelsea Boot Black Leather Pointed Toe Ankle Boots Size 10 | Color: Black/Brown | Size: 10

Madewell ‘The Grayson’ Chelsea Boot Black Leather Pointed Toe Ankle Booties Size: 10 Color: Black & Brown Style: J8293 Condition: Preloved Condition (Normal Signs Of Wear; Small Flaws To Leather Noted; Creasing At Toe Noted; Please See/Zoom In To All... more

$50.00

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Best Seller
Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond Color 7 | Color: Brown/Tan | Size: 7

Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond Color 7 | Color: Brown/Tan | Size: 7

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

$128.00

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® Hillmont Chelsea Leather Cold Weather Boots|dress Shoes

® 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

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® Hillmont Chelsea Leather Cold Weather Boots|dress Shoes

® 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

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® Burleigh Chelsea Leather/waterproof Boots|dress Shoes

® 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

$180.00

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KaLI_store Mens Shoes Men s Boots Boots for Men Casual Boots Motorcycle Combat Ankle Dress Boots Mens Khaki 9

KaLI_store Mens Shoes Men s Boots Boots for Men Casual Boots Motorcycle Combat Ankle Dress Boots Mens Khaki 9

Men Boots Comfortable Fashion Breathable Lace Up Solid Color Outdoor Autumn Winter Wide Calf Leather Boot Description: Gender: Men Boy Upper Material:Artificial leather Sole Material: Rubber Scenes:Indoor&Outdoor Fashion Leisure Style:Comfortable... more

$51.24 $45.96

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KaLI_store Shoes for Men Men s Boots Boots for Men Casual Boots Motorcycle Combat Ankle Dress Boots Mens Black 13

KaLI_store Shoes for Men Men s Boots Boots for Men Casual Boots Motorcycle Combat Ankle Dress Boots Mens Black 13

Mens Shoes High Top Elastic Band Sport Shoes Fashion Casual Shoes Mens Plus Size Ankle Boots Slip on Boots for Men Gender: Men boy Upper Material:Artificial leather Sole Material: Rubber Scenes: Indoor&Outdoor Fashion Leisure Style: Princess Casual Toe... more

$45.07 $40.43

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Madewell Shoes | Madewell The Grayson Chelsea Black Boot Size 9 Bootie Ankle Boots | Color: Black | Size: 9

Madewell Shoes | Madewell The Grayson Chelsea Black Boot Size 9 Bootie Ankle Boots | Color: Black | Size: 9

Madewell The Grayson Chelsea Black Boot Size 9 Bootie Ankle Boots Wear To Toes- Scuffing. Rubbing. Minor Scratching At Heels. Gently Used. Good Condition. Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toeand Cut... more

$50.00

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Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond 7 | Color: Brown/Tan | Size: Various

Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond 7 | Color: Brown/Tan | Size: Various

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

$128.00

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Free People Shoes | Free People Essential Chelsea Boots In Natural Cream Ankle Boots Size 38 Euc | Color: Cream | Size: 8

Free People Shoes | Free People Essential Chelsea Boots In Natural Cream Ankle Boots Size 38 Euc | Color: Cream | Size: 8

Free People Tan Leather Ankle Boots Made In Spain Size 38/8 Euc No Box more

$90.00

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Free People Shoes | Free People James Chelsea Boots White Leather Lug Sole Ankle Boots In Bone 40 | Color: White | Size: 9

Free People Shoes | Free People James Chelsea Boots White Leather Lug Sole Ankle Boots In Bone 40 | Color: White | Size: 9

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

$54.00

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Coach Shoes | Coach Boots Mens 10.5 Brown Leather Chukka Boots Shoes Ankle Boots | Color: Brown | Size: 10.5

Coach Shoes | Coach Boots Mens 10.5 Brown Leather Chukka Boots Shoes Ankle Boots | Color: Brown | Size: 10.5

Coach Boots Mens 10.5 Brown Leather Chukka Boots Shoes Ankle Boots. Flaw: Leather Peeling On The Inside Please See Pictures. On The Outside No Flaws. Questions? Leave A Comment Below! more

$48.00

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Free People Shoes | Free People Lonesome Fringe Ankle Boot Suede Ankle Boot With Fringe. Size 8 | Color: Brown | Size: 8

Free People Shoes | Free People Lonesome Fringe Ankle Boot Suede Ankle Boot With Fringe. Size 8 | Color: Brown | Size: 8

Lonesome Fringe Ankle Boot By Free People. Suede Ankle Boot With Foldover Top And Fringe Trimming. Leather Wrapped Chord Detailing Around The Ankle. Leather Tab Detailing At Each Bottom Side And Back Low Stacked Heel. Gently Worn With Only 2 Marks As... more

$100.00

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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 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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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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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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Madewell Shoes | New Madewell Sonia Snake Embossed Chelsea Block Heel Ankle Boots Size 7.5 | Color: Black/Tan | Size: 7.5

Madewell Shoes | New Madewell Sonia Snake Embossed Chelsea Block Heel Ankle Boots Size 7.5 | Color: Black/Tan | Size: 7.5

New Madewell Sonia Snake Embossed Low Chelsea Block Heel Ankle Boots Size 7.5 - Almond Toe Tapered, Stacked Heel - Chelsea Boot - 1 3/4" Heel, 3" Shaft - Pull-On Style - Elastic Gore Insets - Cushioned Footbed - Leather Upper And Lining/Synthetic Sole... more

$99.00

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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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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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Coach Shoes | Coach Suffolk Patchwork Black Leather Chelsea/Ankle Boots, Snakeskin, Calf, 6.5 | Color: Black | Size: 6.5

Coach Shoes | Coach Suffolk Patchwork Black Leather Chelsea/Ankle Boots, Snakeskin, Calf, 6.5 | Color: Black | Size: 6.5

Excellent Used Conditions Worn Once No Notable Scuffs Or Flaws Elevate Your Style With These Stunning Coach Suffolk Patchwork Black Leather Chelsea/Ankle Boots. These Boots Feature A Unique Patchwork Design And A Sleek Black Color That Complements Any... more

$55.00

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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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Tory Burch Shoes | New.....Tory Burch Chelsea Black Ankle Boot...Size 10 | Color: Black | Size: 10

Tory Burch Shoes | New.....Tory Burch Chelsea Black Ankle Boot...Size 10 | Color: Black | Size: 10

Classic Chelsea Boot Defined By Elasticated Sides And A Back Pull Tab Features A Refined Profile With A Pointed Toe. Crafted In Smooth Calf Leather With A Buffed Leather Sole.Read Less 1.77" Heel Shaft Height: 17.3cm Calf Leather Upper; Elastic Trim... more

$149.00

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Free People Shoes | Free People Brooks Chelsea Ankle Boots | Color: Green | Size: 6.5

Free People Shoes | Free People Brooks Chelsea Ankle Boots | Color: Green | Size: 6.5

Leather Upper Ankle-High Chelsea Boot Shaft Zipper Closure Lightly Cushioned Footbed Lug Outsole Pull-On New Without Box Size 36.5 (6.5) more

$110.00

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Free People Shoes | Free People Maverick Black Leather Chelsea Boots Western Ankle Booties | Color: Black | Size: 8

Free People Shoes | Free People Maverick Black Leather Chelsea Boots Western Ankle Booties | Color: Black | Size: 8

Reposhing This Item I Purchased From @Pinetreeposh. Loved It, But They Are Too Small I’m Usually A 9 Or 9.5. These Fit So Snug, I Would Compare Them To An 8, Maybe An 8.5. more

$100.00

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Gucci Shoes | Gucci Worsh Black Leather Chelsea Ankle Boots | Color: Black | Size: 11

Gucci Shoes | Gucci Worsh Black Leather Chelsea Ankle Boots | Color: Black | Size: 11

Only Wore Once To Big It Comes With Original Box And Dust Bags As Well In Great Condition No Scratches Or Marks more

$950.00

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Anthropologie Shoes | Anthropologie Taupe Tan Brown Leather Pull-On Chelsea Ankle Boots Size 9 | Color: Brown/Tan | Size: 9

Anthropologie Shoes | Anthropologie Taupe Tan Brown Leather Pull-On Chelsea Ankle Boots Size 9 | Color: Brown/Tan | Size: 9

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

$35.00

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Coach Shoes | Coach Chelsea Leather Ankle Boot | Color: Green | Size: 10

Coach Shoes | Coach Chelsea Leather Ankle Boot | Color: Green | Size: 10

Leather Upper Man-Made Leather Lining And Footbed Leather Outsole Pull On Side Gore In Darker Green Nwot. Box Not Included. Smells Of Leather. No Flaws. Fast Shipping. more

$118.00

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Madewell Shoes | - Madewell Chelsea Tan Slip On Ankle Boots Sz 9 | Color: Tan | Size: 9

Madewell Shoes | - Madewell Chelsea Tan Slip On Ankle Boots Sz 9 | Color: Tan | Size: 9

Tan Leather With Elastic Stretch On Both Side For Easy Slip On Round Toe Leather Sole Preowned But In Good Condition more

$65.00

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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 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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