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Madewell Shoes | Madewell White Grayson Brogue Chelsea Suede Leather Western Ankle Booties Size 6 | Color: Tan/White | Size: 6

Madewell Shoes | Madewell White Grayson Brogue Chelsea Suede Leather Western Ankle Booties Size 6 | Color: Tan/White | Size: 6

Brand: Madewell Style: The Grayson Brogue Chelsea Suede Leather Western Cowgirl Ankle Booties Shoes Size: 6 Color: Bone White & Tan Heel Height: 2" Condition: Pre-Owned. There Are Some Minor Blemishes On The Suede. See Pictures For Details. Otherwise,... more

$48.00

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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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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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Slip-on Chelsea Ankle Boots

Slip-on Chelsea Ankle Boots

Men's Tod's Slip-on Chelsea Ankle Boots - Brown - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 1.5cm 100% Calf Leather, 100% Rubber. Made in Italy. more

$694.65 $566.83

FREE shipping

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Shield Square-toe Chelsea Ankle Boots

Shield Square-toe Chelsea Ankle Boots

Men's Burberry Shield Square-toe Chelsea Ankle Boots - Black - Casual boots 65% Calf Leather, 25% Polyester, 10% Rubber, Lining: 70% Calf Leather, 12% Polyester, 10% Goatskin Leather, 8% Rubber. Made in Italy. more

$1,106.62 $885.29

FREE shipping

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Henry Ankle Chelsea Boot

Henry Ankle Chelsea Boot

Men's Tricker's Henry Ankle Chelsea Boot - Black - Casual boots 100% Leather. Made in Italy. more

$732.05 $597.36

FREE shipping

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

Madewell Shoes | Madewell The Grayson Chelsea Boot Black Leather Pointed Toe Ankle Booties | 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

$75.00

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Free People Shoes | Free Peoples Lug Sole Chunky Heel Ankle Bootie James Chelsea White Leather New | Color: White | Size: Various

Free People Shoes | Free Peoples Lug Sole Chunky Heel Ankle Bootie James Chelsea White Leather New | Color: White | Size: Various

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 Insole... more

$150.00

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Madewell Shoes | Madewell Ainsley Tan Leather Chelsea Boots Ankle Booties | Color: Brown/Tan | Size: 7

Madewell Shoes | Madewell Ainsley Tan Leather Chelsea Boots Ankle Booties | Color: Brown/Tan | Size: 7

Lovely Madewell "Ainsley" Leather Chelsea Boots! Pull On Style With A Low Heel And An Almond Toe. Gently Worn And In Excellent Condition, Size 7. more

$79.00

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

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

Madewell Pull On Ankle Boot Size 9.5 Regan Black Leather Chelsea J8307 Booties Excellent Preowned Condition. Madewell Regan Size 9.5 Black Leather Upper And Lining Stacked Heel 2.5 " Heel Cloudlift Lite Padding Retails For $178 Style J8307 Hard To... more

$71.00

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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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Madewell Shoes | Madewell 8.5 Caleb Black Leather Bootie Low Asymmetrical Boots Chelsea Ankle | Color: Black | Size: 8.5

Madewell Shoes | Madewell 8.5 Caleb Black Leather Bootie Low Asymmetrical Boots Chelsea Ankle | Color: Black | Size: 8.5

Gently Used Madewell Womens 8.5 Caleb Black Leather Bootie Low Asymmetrical Boots Chelsea Ankle Black Low Cut 10.75 Inches Long 3.5 Inches Sole Width 1.5 Heel Evidence Of Use On The Sole Insole And Upper Please Review All Photos Carefully more

$29.00

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Madewell Shoes | Madewell Black Sonia Leather Chelsea Ankle Bootie | Color: Black | Size: 9

Madewell Shoes | Madewell Black Sonia Leather Chelsea Ankle Bootie | Color: Black | Size: 9

An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. 1 3/4" Heel 3" Shaft Pull-On Style With Elastic Gore Insets Cushioned Footbed Leather Upper And Lining/Synthetic Sole... more

$125.00

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Free People Shoes | Free People Shadow Lark Cure Blue Leather Ankle Chelsea Bootie Sz 6 | Color: Blue | Size: 6

Free People Shoes | Free People Shadow Lark Cure Blue Leather Ankle Chelsea Bootie Sz 6 | Color: Blue | Size: 6

Free People Shadow Lark Ankle Chelsea Bootie Sz 6 Navy Perforated Leather Hidden Snaps On One Side Side Zipper On Other Side Ankle Boots, Chelsea Style Small Heel Cute Stitched Detail On Side Size 36 Pre-Owned Have Some Wear But Still Lots Of Left... more

$45.00

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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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Free People Shoes | Free People Brown Leather Chelsea Ankle Booties 38 | Color: Brown | Size: 8

Free People Shoes | Free People Brown Leather Chelsea Ankle Booties 38 | Color: Brown | Size: 8

Free People Brown Leather Chelsea Ankle Booties - Zip Up Heels - Leather Sole - Heel Height: 1” Size: Euro 38 / 8 (Hj) more

$55.00

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Madewell Shoes | Madewell Otis Tan Brown Leather Pull-On Chelsea Ankle Booties Boots | Color: Tan | Size: 6.5

Madewell Shoes | Madewell Otis Tan Brown Leather Pull-On Chelsea Ankle Booties Boots | Color: Tan | Size: 6.5

Previously Loved In Good Condition, Some Wear On The Upper And Soles With Lots Of Life Left; Small Tear On Leather Lining Of Inside Left Boot. Tan Leather Colorway, Women’s Size 6.5 Refer To Pictures And Reach Out With Any Questions Bundle Items To... more

$49.00

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Kate Spade Shoes | Kate Spade New York Leah Chelsea Block Heel Black Leather Ankle Booties Boots | Color: Black | Size: 9.5

Kate Spade Shoes | Kate Spade New York Leah Chelsea Block Heel Black Leather Ankle Booties Boots | Color: Black | Size: 9.5

Kate Spade New York Leah Chelsea Block Heel Black Leather Ankle Booties Boots. Size 9.5. Pull On Boot. Leather Wrapped Heel. Gold Tone Spade On Back Of Boot 2.5" Block Heel In Very Good Pre-Owned Condition With Slight Signs Of Wear/Slight Wear On... more

$68.00

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Madewell Shoes | Madewell Booties Bryce Suede Leather Chelsea Ankle Black Size 10 Style M4674 | Color: Black | Size: 10

Madewell Shoes | Madewell Booties Bryce Suede Leather Chelsea Ankle Black Size 10 Style M4674 | Color: Black | Size: 10

Madewell Booties Bryce Suede Leather Chelsea Ankle Black Size 10 Style M4674. Madewell Bryce Ankle Boots Booties Black Suede Leather M4674 Side Zip Biker Westernexcellent Condition more

$59.00

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J. Crew Shoes | J. Crew Black Leather Lug Sole Chunky Chelsea Boots Ankle Booties Size 8 Euc | Color: Black | Size: 8

J. Crew Shoes | J. Crew Black Leather Lug Sole Chunky Chelsea Boots Ankle Booties Size 8 Euc | Color: Black | Size: 8

J. Crew Black Leather Lug Sole Chunky Chelsea Boots Ankle Booties Size 8 Euc Excellent Like New Condition With No Flaws Round Toe Ankle-Boot Leather Flat Anti-Slip Rubber Outsole Slip-On Style Elasticized Opening Boho Outdoor Travel Combat Military... more

$75.00

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Madewell Shoes | Madewell Lonny Black Leather Heeled Chelsea Ankle Booties Size 8 | Color: Black | Size: 8

Madewell Shoes | Madewell Lonny Black Leather Heeled Chelsea Ankle Booties Size 8 | Color: Black | Size: 8

Style #07952 Condition: Good Used Condition, Some Signs Of Wear (See Photos) more

$40.00

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Free People Shoes | Free People Brown Atlas Studded Chelsea Leather Ankle Boots Bootie Eu 37 | Color: Brown | Size: 37eu

Free People Shoes | Free People Brown Atlas Studded Chelsea Leather Ankle Boots Bootie Eu 37 | Color: Brown | Size: 37eu

These Boots Are Like New! The Brown And Gold Make For A Great Combination. Questions? Leave A Comment Below! more

$98.00

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Free People Shoes | Free People "Atlas" Black Puffer And Leather Chelsea Ankle Boot / Bootie | Color: Black/Gold | Size: 9.5 Us / 39.5 Eu

Free People Shoes | Free People "Atlas" Black Puffer And Leather Chelsea Ankle Boot / Bootie | Color: Black/Gold | Size: 9.5 Us / 39.5 Eu

Free People "Atlas" Black Puffer And Leather Chelsea Ankle Boot / Bootie Say Hello To The Perfect, Most Versatile Boot. The Ankle Height Makes This Style Easily Transition From Day To Night. Wear Them With Your Favorite Skinny Jeans And Tee For A More... more

$90.00

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Free People Shoes | Free People “Lost Valley” Ankle Booties Leather Size 7 / Leather Booties / Fall | Color: Tan | Size: 7

Free People Shoes | Free People “Lost Valley” Ankle Booties Leather Size 7 / Leather Booties / Fall | Color: Tan | Size: 7

Free People “Lost Valley” Ankle Booties Leather Size 7 . Brown/ Tan . Great Fall Wardrobe Staple! more

$60.00

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Madewell Shoes | Madewell The Bohnam Chelsea Boot Ankle Boots Booties Black Western Size 8.5 | Color: Black | Size: 8.5

Madewell Shoes | Madewell The Bohnam Chelsea Boot Ankle Boots Booties Black Western Size 8.5 | Color: Black | Size: 8.5

Madewell The Bohnam Chelsea Boot Ankle Boots Booties Black Western Size 8.5. Leather Boots, Pointed Toe, Wood 2” Block Heel. more

$45.00

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Madewell Shoes | Madewell Grayson Chelsea Velvet Ankle Boots / Booties / Shooties Size 9 Country | Color: Silver | Size: 9

Madewell Shoes | Madewell Grayson Chelsea Velvet Ankle Boots / Booties / Shooties Size 9 Country | Color: Silver | Size: 9

Madewell Genuine Leather Grayson Chelsea Velvet Ankle Boots Size 9, Small Spots Hardly Noticeable See Picture 9, Otherwise These Boots Are In Excellent Used Condition. more

$30.00

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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 | Free People Gold Croc Embossed Beau Western Chelsea Ankle Booties | Color: Gold | Size: 41eu

Free People Shoes | Free People Gold Croc Embossed Beau Western Chelsea Ankle Booties | Color: Gold | Size: 41eu

In Excellent Condition Other Than A Minor Scuff On Side See Last Photo, Gold Metallic Croc Embossed, Leather, Pointed Toe, Pull On Style, Size 41. Small Heel #Blkrk more

$150.00

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Madewell Shoes | Madewell Bryce Chelsea Suede Ankle Boot Tan Brown Low Heel Flat Bootie 8.5 | Color: Brown/Tan | Size: 8.5

Madewell Shoes | Madewell Bryce Chelsea Suede Ankle Boot Tan Brown Low Heel Flat Bootie 8.5 | Color: Brown/Tan | Size: 8.5

Madewell Bryce Chelsea Suede Ankle Boot Low Heel Genuine Leather Suede Tan Camel Chestnut Brown Color - Neutral For Fall Pull On Style Terrific Condition Size 8.5 more

$40.00

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J. Crew Shoes | J Crew Cognac Brown Chelsea Pull On Boots Ankle Booties Size 8 Eo824 | Color: Brown | Size: 8

J. Crew Shoes | J Crew Cognac Brown Chelsea Pull On Boots Ankle Booties Size 8 Eo824 | Color: Brown | Size: 8

J Crew Cognac Brown Leather Chelsea Boots With Stretch Panels For Easy Pull-On. Tag Size 8. Fits 7.5-8 In My Opinion. Style Eo824 Preowned. Shows Signs Of Wear Including Scuffs On Toes, Wear On Back Heels, Wear On Bottoms Of Soles, Creasing In Midfoot... more

$50.00

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Free People Shoes | Free People Shadow Lark Ankle Chelsea Bootie | Color: Blue | Size: 36

Free People Shoes | Free People Shadow Lark Ankle Chelsea Bootie | Color: Blue | Size: 36

The Cutest Booties That I’ve Been Holding On To. They Have Natural Distressed Color. The Bottoms Are Like This Wooden Sole, So The Bottom Has That Same Worn Distressed Look From Being Worn. Tts Navy Perforated Leather Snaps On One Side, Zipper On The... more

$45.00

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

Free People Shoes | Free People Black Croc Embossed Beau Western Chelsea Boot Ankle Booties | Color: Black | 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 | Free People James Chelsea Black Boots Chunky Feels Ankle Booties 38.5 Us 8.5 | Color: Black/Cream | Size: 8.5

Free People Shoes | Free People James Chelsea Black Boots Chunky Feels Ankle Booties 38.5 Us 8.5 | Color: Black/Cream | Size: 8.5

New With Box Size 38.5 / Us 8.5 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... more

$180.00

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Coach Shoes | Coach Oakdale Bootie In Slate, Leather Pointed Ankle Booties Shoes. Size: 5.5 | Color: Tan | Size: 5.5

Coach Shoes | Coach Oakdale Bootie In Slate, Leather Pointed Ankle Booties Shoes. Size: 5.5 | Color: Tan | Size: 5.5

Oakdale Suede Booties Wedges Beautiful Coach Wedge Booties. Tan Suede Brand New In Box, See Close Up. The Heel Is 3.5" Interior Zipper Closure With Silver Hardware. Looks Great With Skinny Jeans Or Skirts. Size: 5.5 more

$169.00

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Free People Shoes | Free People Beau Western Boot Eu 36 Us 6 Gold Ankle Chelsea Bootie Croc Pointed | Color: Gold | Size: 36eu

Free People Shoes | Free People Beau Western Boot Eu 36 Us 6 Gold Ankle Chelsea Bootie Croc Pointed | Color: Gold | Size: 36eu

Free People Beau Western Boot In Gold Size 36 (Equivalent To A Us Women's Size 6 Per Free People Website) Slip-On Western-Style Chelsea Boot Silhouette Ankle-Height Shaft Lightly-Distressed Metallic Gold Croc Embossed Leather Upper Pointed Snip Toe... more

$53.00

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Free People Shoes | Free People Venture Woven Leather Suede Ankle Booties Gray Boho Booties Size 7 | Color: Gray | Size: 7

Free People Shoes | Free People Venture Woven Leather Suede Ankle Booties Gray Boho Booties Size 7 | Color: Gray | Size: 7

Free People Venture Woven Leather Suede Ankle Booties Gray Boho Booties Size 7 Gray Suede Upper, With A Woven Texture. Brown Wood Stacked Heels. Pointy Toe Leather Outsole Crisscross Straps With Buckle Detail. Women’s Size 7 (Euro 37) Gently Used With... more

$69.00

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Free People Shoes | Free People Black Leather Strappy Block Heel Ankle Hybrid Ankle Booties Eu 39 | Color: Black | Size: 39eu

Free People Shoes | Free People Black Leather Strappy Block Heel Ankle Hybrid Ankle Booties Eu 39 | Color: Black | Size: 39eu

The Free People ‘Hybrid’ Genuine Black Leather Ankle Boots Have A Manufacturer Distressed Upper, Round Toe And Strappy, Banded Upper For A Cutout Peekaboo Effect At Ankle. Elastic Inset On Inner Side Of Vamp And Rear Zipper For Pull-On Wear. Chunky... more

$80.00

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Madewell Shoes | Madewell Black Chelsea Heeled Ankle Booties 8.5 | Color: Black | Size: 8.5

Madewell Shoes | Madewell Black Chelsea Heeled Ankle Booties 8.5 | Color: Black | Size: 8.5

Madewell Black Heeled Chelsea Boots In Size 8.5. Used But In Good Condition. Very Comfortable Booties That Are Easy To Walk In With A Chunky Heel. more

$50.00

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J. Crew Shoes | J Crew Ankle Booties 9.5 Tan Suede Pointy Toe Western Pull On Chelsea Boots | Color: Tan | Size: 9.5

J. Crew Shoes | J Crew Ankle Booties 9.5 Tan Suede Pointy Toe Western Pull On Chelsea Boots | Color: Tan | Size: 9.5

J Crew Womens Ankle Booties Size 9.5 Tan Suede Pointy Toe Western Pull On Chelsea Boots Heel 3 Shaft Height 7.5 Around Ankle 12 Pet Free Home Smoke Free Home Offers Welcome more

$168.00

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Free People Shoes | Free People Dark Horse Chelsea Ankle Booties | Color: White | Size: 9

Free People Shoes | Free People Dark Horse Chelsea Ankle Booties | Color: White | Size: 9

Free People Dark Horse Chelsea Ankle Booties Pre Owned Still In Good Condition Size 39 Please See Pictures For More Details more

$50.00

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More information about Men's Shoes

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