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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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Best Seller
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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Zara Shoes | Leather Chelsea Ankle Boots Sz 6 | Color: Black | Size: 6

Zara Shoes | Leather Chelsea Ankle Boots Sz 6 | Color: Black | Size: 6

Leather Chelsea Ankle Boots Sz 6 #47-823 more

$59.00

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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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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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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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Madewell Shoes | Madewell The Bryce Ankle Suede Chelsea Boot, Tan Desert | Sz 7.5 | Color: Cream/Tan | Size: 7.5

Madewell Shoes | Madewell The Bryce Ankle Suede Chelsea Boot, Tan Desert | Sz 7.5 | Color: Cream/Tan | Size: 7.5

Suede Upper Leather Lining Needs Some Tlc But Still Lots Of Life In Them G1910 more

$34.00

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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 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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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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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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Kate Spade Shoes | Kate Spade Scalloped Garden Black Leather Ankle Chelsea Boot ~ Sz 9.5 | Color: Black | Size: 9.5

Kate Spade Shoes | Kate Spade Scalloped Garden Black Leather Ankle Chelsea Boot ~ Sz 9.5 | Color: Black | Size: 9.5

Kate Spade Scalloped Garden Black Leather Ankle Chelsea Boot ~ Sz 9.5 Retail Price $325.00 + Tax Since The '60s, Chelsea Boots Have Been Worn By Leggy Fashion Icons And Supermodels Around London's Trendy Chelsea Neighborhood (Hence The Name). This Kate... more

$160.00

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

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

Nwob, No Flaws! Free People Atlas Chelsea Puffer Boot, Black These Adorable Boots Sold Out Instantly Everywhere! Multiple Sizes Avail Gleaming Studs And Scalloped Edges Contrast Against The Puffy Profile Of A So-Cool Chelsea Boot Crafted From Leather.... more

$82.00

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Madewell Shoes | Madewell “Grayson” Tan Suede Leather Brogue Chelsea Heeled Ankle Boots/Booties | Color: Orange/Tan | Size: 7

Madewell Shoes | Madewell “Grayson” Tan Suede Leather Brogue Chelsea Heeled Ankle Boots/Booties | Color: Orange/Tan | Size: 7

Madewell “Grayson” Tan Suede Leather Stocked Block Heel Ankle Boots/Booties. Our Design Team Took Age-Old Western Boot Details, A Stacked Raw Leather Heel, A Pointy Toe, Brogue Perforations And Cut Them Low On The Ankle To Make Your Legs Look Even... more

$69.00

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Anthropologie Shoes | Anthropologie Sixtyseven Distressed Croc Leather Boho Chelsea Ankle Boots | Color: Black | Size: 37eu

Anthropologie Shoes | Anthropologie Sixtyseven Distressed Croc Leather Boho Chelsea Ankle Boots | Color: Black | Size: 37eu

Great Used Condition. Distressed Croc Chelsea Ankle Boots By Anthropologie Brand Sixtyseven In Black. Chic, Edgy Aesthetic, A Versatile Capsule Wardrobe Piece For The Season That Can Be Dressed Up Or Worn Casually. Slip-On Ankle Boots With Textured... more

$50.00

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Kate Spade Shoes | Kate Spade New York Ankle Chelsea Boots | Color: Black | Size: 10

Kate Spade Shoes | Kate Spade New York Ankle Chelsea Boots | Color: Black | Size: 10

Kate Spade New York Ankle Chelsea Boots Black & Metallic Leather & Rubber Trim Round-Toes With Glitter Accents Heels: 1.5" Size: 10 In Good Condition, Small Spots On Boots Where Glitter Is Scratched From Being In Closet. - You Can See By The Soles... more

$28.00

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Madewell Shoes | Madewell The Chelsea Shearling Ankle Boots | Color: Tan | Size: 7

Madewell Shoes | Madewell The Chelsea Shearling Ankle Boots | Color: Tan | Size: 7

Cute, Comfortable And Stylish!! Leather Upper. Has Shearling Inside Boots, Slip On Style, Elasticized Panel, No Modeling Or Trades, Good Preowned Condition With Signs Of Use more

$92.00

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Free People Shoes | Free People Gold Embossed Beau Western Chelsea Ankle Boot 38 New W/Out Box | Color: Black/Gold | Size: 38

Free People Shoes | Free People Gold Embossed Beau Western Chelsea Ankle Boot 38 New W/Out Box | Color: Black/Gold | Size: 38

Fabulous Free People Metallic Gold Leather Crocodile Embossed Chelsea Ankle Boot New But No Box. Size 38 Block Heel @1.5” Leather Upper, Lining And Sole With Elastic Side Gussets Welt Stitching more

$82.00

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Tory Burch Shoes | $500 Tory Burch Medallion-Plaque Ankle Boot Chelsea River Rock Suede 9 (Db12) | Color: Brown | Size: 9

Tory Burch Shoes | $500 Tory Burch Medallion-Plaque Ankle Boot Chelsea River Rock Suede 9 (Db12) | Color: Brown | Size: 9

Floor Model And Tried On - Excellent Like New -Please Refer To Pictures Our Minimalist Ankle Boot Is A Fall Essential. Crafted In Smooth Leather, It Has A Comfortable Cushioned Insole And Flattering Almond Toe (Square Off). The Stacked Block Heel Pairs... more

$185.00

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Madewell Shoes | Madewell Mahogany Leather Ankle Chelsea Boots 7.5 | Color: Brown/Red | Size: 7.5

Madewell Shoes | Madewell Mahogany Leather Ankle Chelsea Boots 7.5 | Color: Brown/Red | Size: 7.5

Madewell Mahogany Leather Ankle Chelsea Boots 7.5 Beautiful Soft Leather, Hardly Used, Gorgeous Deep Chestnutty Brown/Wine Color. more

$80.00

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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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More information about Men's Shoes

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