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Anthropologie Shoes | Anthropologie Silent D Alwin Green Suede Ankle Cuff Boho Chunky Heel Ankle Boots | Color: Green | Size: 10

Anthropologie Shoes | Anthropologie Silent D Alwin Green Suede Ankle Cuff Boho Chunky Heel Ankle Boots | Color: Green | Size: 10

Anthropologie Silent D Green Suede Ankle Cuff Chunky Heel Ankle Boots Beautiful Moss Olive Green Suede Fold Over Cuff Ankle Outer Zipper Closure With Tassel String Almond Shape Toe Cushioned Insole 2.5 Inch Stacked Wood Chunky Heel Gently Used In... more

$100.00

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Kate Spade Shoes | Kate Spade New York Taupe Suede Ankle Boot W/Chunky Heel And Suede Bow At Ankle | Color: Cream/Gray | Size: 9.5

Kate Spade Shoes | Kate Spade New York Taupe Suede Ankle Boot W/Chunky Heel And Suede Bow At Ankle | Color: Cream/Gray | Size: 9.5

This Bootie Is An Easy Way To Step Up Your Street Style--And Maintain An Enviable Strut. A Chic Suede Bow Accents This Everyday Bootie's Much-Appreciated Comforts, Such As Its Stacked Heel And Rounded Toe. A Few Scuffs And Spots And Wear To Sole As... more

$100.00

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Kate Spade Shoes | Kate Spade New York Taupe Suede Ankle Boot W/Chunky Heel And Suede Bow At Ankle | Color: Tan | Size: 10

Kate Spade Shoes | Kate Spade New York Taupe Suede Ankle Boot W/Chunky Heel And Suede Bow At Ankle | Color: Tan | Size: 10

This Bootie Is An Easy Way To Step Up Your Street Style--And Maintain An Enviable Strut. A Chic Suede Bow Accents This Everyday Bootie's Much-Appreciated Comforts, Such As Its Stacked Heel And Rounded Toe. A Few Scuffs And Spots And Wear To Sole As... more

$60.00

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WIDE FIT Jackie Lace Up Ankle Boot - black

WIDE FIT Jackie Lace Up Ankle Boot - black

Walk it out in confidence with the Jackie Lace Up Ankle Boot. These black boots are must-haves with their quilted detailing and chunky heels. A lace-up style with a convenient side zip, you'll be comfortable all day long in this wide fit.Key Features... more

$109.99 $76.99

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WIDE FIT Jackie Lace Up Ankle Boot - black

WIDE FIT Jackie Lace Up Ankle Boot - black

Walk it out in confidence with the Jackie Lace Up Ankle Boot. These black boots are must-haves with their quilted detailing and chunky heels. A lace-up style with a convenient side zip, you'll be comfortable all day long in this wide fit.Key Features... more

$109.99 $76.99

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WIDE FIT Jackie Lace Up Ankle Boot - black

WIDE FIT Jackie Lace Up Ankle Boot - black

Walk it out in confidence with the Jackie Lace Up Ankle Boot. These black boots are must-haves with their quilted detailing and chunky heels. A lace-up style with a convenient side zip, you'll be comfortable all day long in this wide fit.Key Features... more

$109.99 $76.99

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Higgins Mill Weatherproof Lug Sole Ankle Boots

Higgins Mill Weatherproof Lug Sole Ankle Boots

Men's Allen Edmonds Higgins Mill Weatherproof Lug Sole Ankle Boots - Black - Casual boots Allen Edmonds "Higgins Mill" lace-up boots in waterproof leather 360o bench welt construction for durability and stability Chunky heel Round toe Lace-up vamp;... more

$495.00

FREE shipping

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Snap Genuine Shearling Ankle Boot

Snap Genuine Shearling Ankle Boot

Men's Bottega Veneta Snap Genuine Shearling Ankle Boot - Brown - Casual boots A chunky Extralight sole with intreccio-style tread grounds this suede pull-on boot lined with plush genuine shearling that offers a cozy element. Pull-on style Removable... more

$990.00

FREE shipping

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Lukas 40 Ankle Boots

Lukas 40 Ankle Boots

Men's Saint Laurent Lukas 40 Ankle Boots - Black - Casual boots Black leather Lukas 40 ankle boots from Saint Laurent featuring an ankle length, a pointed toe, a side zip fastening, a chunky low block heel and a metallic pull tab. more

$1,068.19 $853.67

FREE shipping

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Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(Black 11)

Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(Black 11)

Sleek lines and a classic design lends this men s lace-up shoe a look that s timeless and modern all at once. The durable rubber outsole has shock-absorbing properties and provides traction for enhanced stability. Goes with everything from suits and... more

$36.28 $30.48

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Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(White 9)

Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(White 9)

Sleek lines and a classic design lends this men s lace-up shoe a look that s timeless and modern all at once. The durable rubber outsole has shock-absorbing properties and provides traction for enhanced stability. Goes with everything from suits and... more

$40.19 $33.76

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Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(Brown 10.5)

Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(Brown 10.5)

Sleek lines and a classic design lends this men s lace-up shoe a look that s timeless and modern all at once. The durable rubber outsole has shock-absorbing properties and provides traction for enhanced stability. Goes with everything from suits and... more

$34.67 $29.12

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Anthropologie Shoes | Anthropologie Casta Sundance Perforated Ankle Boot Size 39 | Color: Cream/Tan | Size: Eu39

Anthropologie Shoes | Anthropologie Casta Sundance Perforated Ankle Boot Size 39 | Color: Cream/Tan | Size: Eu39

Genuine Leather And Suede Upper With Rubber Sole. Size 39 Measurement Of Sole From Heel To Toe Is About 10". No Flaws; Excellent Used Condition. more

$50.00

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Free People Shoes | Free People Gigi Chunky Platform Purple Suede Ankle Boots | Color: Purple | Size: 38.5

Free People Shoes | Free People Gigi Chunky Platform Purple Suede Ankle Boots | Color: Purple | Size: 38.5

New Without The Box No Rips No Flaws Size 38.5 Purple Color Smoke And Pet Free Home more

$150.00

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Kate Spade Shoes | Kate Spade Sequin Leopard Print Langley Ankle Boots Euc Shiny Cute Chunky Heel | Color: Tan | Size: 6.5

Kate Spade Shoes | Kate Spade Sequin Leopard Print Langley Ankle Boots Euc Shiny Cute Chunky Heel | Color: Tan | Size: 6.5

Take Your Style This Season To A New Level Wearing The Kate Spade New York Langley Booties. Sequin Kid Suede Upper. Velvet Bow At The Shaft. Round Silhouette. Inside Zipper Closure. Leather Lining And Footbed. Wrapped Rounded Chunky Heel. Leather... more

$85.00

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Free People Shoes | Free People Black Suede Boots Cecile Chunky Mid Block Heel Ankle Size 41 | Color: Black | Size: 41eu

Free People Shoes | Free People Black Suede Boots Cecile Chunky Mid Block Heel Ankle Size 41 | Color: Black | Size: 41eu

Free People Black Suede Boots Cecile Chunky Mid Block Heel Ankle Boots Classic Suede Ankle Boots In A Chic Shape And Trendy Distressed Look. Rounded Distressed Toe And Blocky Heel. Great Preowned Condition With Minimal Signs Of Previous Wear Size 41 2... more

$58.00

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J. Crew Shoes | J Crew Italian Leather Chunky Heel Ankle Boots | Color: Black | Size: 9.5

J. Crew Shoes | J Crew Italian Leather Chunky Heel Ankle Boots | Color: Black | Size: 9.5

Womens, J Crew "Aggie", Italian Leather Chunky Heel, Ankle Boots. Side Zippered Closure With Cushioned Insoles Leather Footbed. Stacked Heels. In Excellent Condition! Sz 9½ Heels 2¾" (Back) ¼" (Front) In Excellent, Clean Preowned Condition! more

$48.00

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Madewell Shoes | Madewell Brenner Ankle Boot Chunky Heel 7.5m Black | Color: Black/Brown | Size: 7.5

Madewell Shoes | Madewell Brenner Ankle Boot Chunky Heel 7.5m Black | Color: Black/Brown | Size: 7.5

Reposhing This Item I Purchased From @Round2chic. Loved Them, But They Are Just A Tiny Bit Too Small. Questions? Leave A Comment Below! more

$50.00

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Free People Shoes | Free People James Chunky Chelsea Ankle Leather Boots- Size 9 | Color: Black/Cream | Size: 9

Free People Shoes | Free People James Chunky Chelsea Ankle Leather Boots- Size 9 | Color: Black/Cream | Size: 9

Reposhing Only Because I Ordered The Wrong Size. Not Sure What I Was Thinking. These Are A 9. (I’m An 8) They Are In Perfect Condition. Questions? Leave A Comment Below! more

$67.00

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American Eagle Outfitters Shoes | American Eagle Outfitters Black White Faux Leather Zip Chunky Ankle Boots Sz 8 M | Color: Black/White | Size: 8

American Eagle Outfitters Shoes | American Eagle Outfitters Black White Faux Leather Zip Chunky Ankle Boots Sz 8 M | Color: Black/White | Size: 8

American Eagle Outfitters Black White Zip Lace Up Faux Leather Fabric Ribbed Elastic Sides Lined Chunky Ankle 2" Heel Boots Sz 8 M Excellent Condition Except For Insole Of Right Boot Caused When Taking Out Price Tag. N3 more

$39.00

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J. Crew Shoes | J. Crew Black Lightweight Leather Chunky Lace Up Nordic Ankle Boots Size 9 | Color: Black | Size: 9

J. Crew Shoes | J. Crew Black Lightweight Leather Chunky Lace Up Nordic Ankle Boots Size 9 | Color: Black | Size: 9

Great Pre-Owned Condition. Light Signs Of Use But Nothing Major An Unlined Version Of The Best-Selling Cold-Weather Nordic Boots, In Smooth, Lightweight Leather That's Great All Year Long. A City Streets-Ready Riff On Classic Hiking Boots, These... more

$50.00

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Coach Shoes | Coach Nancie Brown Leather Gold Buckle Chunky Heel Short Ankle Boots | Color: Brown/Gold | Size: 7

Coach Shoes | Coach Nancie Brown Leather Gold Buckle Chunky Heel Short Ankle Boots | Color: Brown/Gold | Size: 7

Coach Nancie Dark Brown Leather Heeled Ankle Boots Brushed Gold Buckle Detail Side Zipper Almond Pointed Toe Wooden Chunky High Heel Made In Italy Good Condition- Minimal Signs Of Wear. See S Shoes Have Been Cleaned & Conditioned Inside & Out For New... more

$149.00

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Free People Shoes | Free People Ludlow Studded Chunky Platform Leather Ankle Boots | Color: Black/Silver | Size: 7.5

Free People Shoes | Free People Ludlow Studded Chunky Platform Leather Ankle Boots | Color: Black/Silver | Size: 7.5

Ludlow Studded Moto Boots By Free People Chunky Platform Sole Leather Upper Studded And Buckle Details Interior Zip Closure Ankle Height Note: Light Fading On Right Toe And Wear On One Buckle - See Photos Otherwise Excellent Condition With No Major... more

$150.00

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Zara Shoes | **Worn Once** Leather Chunky Ankle Boots Blogger Fav | Color: Cream | Size: 8.5

Zara Shoes | **Worn Once** Leather Chunky Ankle Boots Blogger Fav | Color: Cream | Size: 8.5

*** Brand New Worn Only Once*** Details Ankle Boots Water Resistant Leather Chunky Elastic Side Panel Cream Low Heel Side Elastic Goring And Back Pull Tab Lug Sole Off White 1128/910 Fyi: Airfit Technical Flexible Latex Foam Insole Designed To Offer... more

$34.00

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Zara Shoes | Euc Zara Chunky Chelsea Combat Black High Ankle Boot Size 39 (8.5) | Color: Black | Size: 8.5

Zara Shoes | Euc Zara Chunky Chelsea Combat Black High Ankle Boot Size 39 (8.5) | Color: Black | Size: 8.5

Excellent Used Condition. Size 39. Ankle Upper Is Stretchy On The Sides. more

$40.00

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Madewell Shoes | Madewell The Ames Black Leather Chunky Stacked Heel Ankle Boot Size 8.5 | Color: Black | Size: 8.5

Madewell Shoes | Madewell The Ames Black Leather Chunky Stacked Heel Ankle Boot Size 8.5 | Color: Black | Size: 8.5

Madewell The Ames Black Leather Chunky Stacked Heel Ankle Boot Excellent, Preowned Condition. Size 8.5 more

$45.00

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Nine West Shoes | Black Size 8 1/2 Sparkling Chunky Sole Ankle Boots | Color: Black | Size: 8.5

Nine West Shoes | Black Size 8 1/2 Sparkling Chunky Sole Ankle Boots | Color: Black | Size: 8.5

Ninewest more

$40.00

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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 Tia Ankle Chelsea Boots Chunky Heel Wine Color Suede Booties Size 8.5 | Color: Red | Size: 8.5

Coach Shoes | Coach Tia Ankle Chelsea Boots Chunky Heel Wine Color Suede Booties Size 8.5 | Color: Red | Size: 8.5

Coach Tia Ankle Chelsea Boots, Chunky Heels, Wine Color Suede Booties, Size 8.5 Women’s. Preowned. Some Wear From Normal Use, Mainly On The Bottoms. Heel Height Approx 2.5”. Elevate Your Shoe Game With These Stylish Coach Tia Ankle Booties In A... more

$60.00

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Coach Shoes | Coach Kasandra Leather Ankle Chunky Boots Cognac Brown Coach Emblem Sz 9 | Color: Brown | Size: 9

Coach Shoes | Coach Kasandra Leather Ankle Chunky Boots Cognac Brown Coach Emblem Sz 9 | Color: Brown | Size: 9

Coach Kasandra Leather Ankle Chunky Boots Cognac Brown Coach Emblem Sz 9 Has Some Creases And Minor Blemishes Inside Boot Has Some Staining But It Does Not Effect The Outside Appearance more

$57.00

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

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

Free People James Chelsea Lug Sole Chunky Ankle Boots In Bone White Size 9 Pre-Owned (No Box) Only Worn Once Or Twice But Has Some Scuffs, Tried To Show In Pictures. more

$60.00

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Zara Shoes | Forever 21 Faux Patent Leather Chunky Platform Lace Up Ankle Boots | Color: Black | Size: 9

Zara Shoes | Forever 21 Faux Patent Leather Chunky Platform Lace Up Ankle Boots | Color: Black | Size: 9

Forever 21 Faux Patent Leather Chunky Platform Lace Up Ankle Boots, Goth Grunge Babe, Inner Zip Closure, Some Creases And Marks From Wear Sz : 8, Best Fits A 9 D1 more

$39.00

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J. Crew Shoes | J.Crew Brown Suede Chukka Desert Field Ankle Boot Lace Up Chunky 8.5 Preppy | Color: Brown | Size: 8.5

J. Crew Shoes | J.Crew Brown Suede Chukka Desert Field Ankle Boot Lace Up Chunky 8.5 Preppy | Color: Brown | Size: 8.5

J. Crew Desert Chukka Ankle Boots. Genuine Butter Soft Suede Upper In Dark Brown. Adjustable Laces. Round Toe. Made In Italy. Leather Lining. Crepe Rubber Sole. Chunky Rugged Classic Preppy Equestrian Casual Chic Collegiate Academia Timeless Retro... more

$50.00

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Jessica Simpson Shoes | Jessica Simpson Black Suede Minimalist Ankle Leather Chunky Heel Boots Size 6 | Color: Black | Size: 6

Jessica Simpson Shoes | Jessica Simpson Black Suede Minimalist Ankle Leather Chunky Heel Boots Size 6 | Color: Black | Size: 6

Jessica Simpson Boots Color: Black Size: 6 Black Suede Upper Partial Inside Zip Closure Pointed Toe Fabric Lining Lightly Padded Footbed Synthetic Sole Imported Worn Once And In Like-New Condition. Purchased From A Sample Sale --- One Of A Kind more

$25.00

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Gucci Shoes | Gucci Ankle Boots Brown Suede Square Toe Elastic Pull On Chunky Uk 9 Us 9.5 | Color: Black/Brown | Size: 9.5

Gucci Shoes | Gucci Ankle Boots Brown Suede Square Toe Elastic Pull On Chunky Uk 9 Us 9.5 | Color: Black/Brown | Size: 9.5

Gucci Boots, Short Ankle Shaft, Brown Suede, Square Toe, Split Shaft, Hidden Elastic Strap For Easy Pull On, Leather Lining, Chunky Heavy Soles With A Block Heel, Made In Italy, Uk 9 / Us 9.5, Insole: 11.5", Outsole: 12", Outsole Width: 4 3/8",... more

$225.00

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Anthropologie Shoes | Khrio Size 9 Leather Ankle Shoes Boots Chunky 2" Heels Size Zipper Silver Band | Color: Black/Silver | Size: 9

Anthropologie Shoes | Khrio Size 9 Leather Ankle Shoes Boots Chunky 2" Heels Size Zipper Silver Band | Color: Black/Silver | Size: 9

Khrio Size 40 Or 9 Leather Ankle Boots Bootie Shoes Chunky 2" Heels Zipper Silver Band Rubber Soles, Pull Tabs. Anthropologie. Boho, Bohemian, Artisan, Arty, Goblincore, Witchcore. Halloween, Witch, Steampunk. Good Used Condition. more

$60.00

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Madewell Shoes | Madewell The Billie Black Leather Chunky Staked Block Heel Ankle Boots | Color: Black/Tan | Size: 7.5

Madewell Shoes | Madewell The Billie Black Leather Chunky Staked Block Heel Ankle Boots | Color: Black/Tan | Size: 7.5

Stride In Style & Comfort Year-Round With These Chic & Versatile Madewell The Billie Leather Chunky Staked Block Heel Booties In Neutral Black With Contrasting Light Brown/Tan Details. In Excellent Preowned Condition, No Stains Or Tears. Size: 7.5... more

$90.00

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Free People Shoes | Free People Snakeskin Leather Chunky Heel Side Zip Ankle Boots Size 41 | Color: Brown/Gray | Size: 41eu

Free People Shoes | Free People Snakeskin Leather Chunky Heel Side Zip Ankle Boots Size 41 | Color: Brown/Gray | Size: 41eu

Free People Snakeskin Leather Chunky Heel Side Zip Ankle Boots Size 41 more

$45.00

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Free People Shoes | Free People James Chelsea Cream Lugged Sole Chunky Ankle Boot, Size 37.5 | Color: Cream | Size: 37.5 (Us 7)

Free People Shoes | Free People James Chelsea Cream Lugged Sole Chunky Ankle Boot, Size 37.5 | Color: Cream | Size: 37.5 (Us 7)

Relatively Lighter Wear, Pre-Owned Condition, But Not Totally Without Blemish. Color: Cream Leather Vamp Side Zipper For Ease Of On And Off Cushioned Interior Foot Bed Expandable Accent Inset For Optimal Comfort Fit Approximate Measurements 6” Shaft... more

$75.00

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Coach Shoes | Coach Nala Bootie Leather Monogram Black Chunky Heel Side Zip Ankle Boot 6 | Color: Black | Size: 6

Coach Shoes | Coach Nala Bootie Leather Monogram Black Chunky Heel Side Zip Ankle Boot 6 | Color: Black | Size: 6

Some Scuffing & Peeling Of Leather On Toe Area Of Boots And Some Wear On Back Chrome Logo On Backs, Overall Good Condition And Wear Is Not Very Noticeable When Worn- See Photos For Details Size 6 Women's See Photos For Details more

$68.00

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More information about Men's Shoes

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