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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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Madewell Shoes | Madewell The Ames Black Leather Chunky Stacked Heel Ankle Boot Bootie Sz 6.5 | Color: Black | Size: 6.5

Madewell Shoes | Madewell The Ames Black Leather Chunky Stacked Heel Ankle Boot Bootie Sz 6.5 | Color: Black | Size: 6.5

Questionsleave A Comment Below Please Note That Unless New Condition Is Specified, Items Are In Pre-Owned Condition And May Have Other Stray Scuffs, Marks, Or Minor Scratches Not Captured. Please Buy Knowing Sold As-Is. more

$65.00

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Best Seller
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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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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Kate Spade Shoes | Kate Spade Bootie Ankle Boots New York Polly Bootie Black Suede Size 9 1/2 M | Color: Black | Size: 9.5

Kate Spade Shoes | Kate Spade Bootie Ankle Boots New York Polly Bootie Black Suede Size 9 1/2 M | Color: Black | Size: 9.5

Kate Spade Bootie Ankle Boots New York Polly Bootie Black Suede Size 9 1/2 M A Gilded Kate Spade Logo Adds Signature Charm To A Streamlined Bootie Crafted From Soft Suede And Lifted By A Stacked Heel. 2" Heel 5" Shaft Pull-On Style Leather Upper And... more

$70.00

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Nine West Shoes | Chana Heeled Leather Straps Buckle Rave Apocalypse Ankle Booties Chunky Block | Color: Black | Size: 8.5

Nine West Shoes | Chana Heeled Leather Straps Buckle Rave Apocalypse Ankle Booties Chunky Block | Color: Black | Size: 8.5

Nine West Chana Leather Chunky Block Heeled Moto Combat Ankle Booties Straps Buckle Zip Tom Raider Rave Apocalypse Underground Grunge Boots Rubber Sole Anti/Slip Winter Rain Water Sz 8.5 See Last Pic, Only Inside Trim. Please Refer To Photos For More... more

$59.00

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Free People Shoes | Free People Taupe Gray Ankle Bootie Boot With Ankle Straps Size 10 41 | Color: Brown/Gray | Size: 10

Free People Shoes | Free People Taupe Gray Ankle Bootie Boot With Ankle Straps Size 10 41 | Color: Brown/Gray | Size: 10

Free People Ankle Boots Size: 10 41 Condition: Pre-Owned In Good Condition. There Are A Few Scratches, But The Color And Material Have A Distressed Flavor, So These Blend In. Features: Slip On Styling, Wrap Around Straps With An Adjustable Brushed... more

$75.00

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Tory Burch Shoes | #Hptory Burch Chunky Heel Ankle Booties | Color: Black | Size: 10 1/2m

Tory Burch Shoes | #Hptory Burch Chunky Heel Ankle Booties | Color: Black | Size: 10 1/2m

#Host Pick Tory Burch Cp Toe Black Leather Ankle Bootie A Geometric Design Patterns The Structural Block Heel Of A Streamlined Cap-Toe Bootie Fashioned From Burnished Leather 4 1/2” Heel 4 1/2" Shaft. Side Zip Closure Leather Upper, Lining And Sole.... more

$160.00

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Coach Shoes | Coach Black Leather Pull On Ankle Booties With Chunky Block Heel | Color: Black | Size: 9.5

Coach Shoes | Coach Black Leather Pull On Ankle Booties With Chunky Block Heel | Color: Black | Size: 9.5

Easy Pull On Elasticized Opening Make This Stylish Yet Comfortable Footwear That Will Last For Years To Come. Versatile, Timeless And Made To Last, These Designer Booties Are Ready To Be Dressed Up Or Down To Complete Any Outfit. Gently Used And... more

$75.00

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Anthropologie Shoes | Anthropologie Leather Lace Up Chunky Heel Ankle Booties J.Shoes Y2k Trendy 2000s | Color: Gray | Size: 8

Anthropologie Shoes | Anthropologie Leather Lace Up Chunky Heel Ankle Booties J.Shoes Y2k Trendy 2000s | Color: Gray | Size: 8

J Shoes Diffuse Booties Ankle Booties Leather Chunky Heels Lace Up Leather Soles Dark Gray Charcoal Gray Size 5.5 more

$29.00

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American Eagle Outfitters Shoes | American Eagle Bootie Above Ankle Faux Suede Leather Size 9.5 Tan Chunky Heel | Color: Tan/White | Size: 9.5

American Eagle Outfitters Shoes | American Eagle Bootie Above Ankle Faux Suede Leather Size 9.5 Tan Chunky Heel | Color: Tan/White | Size: 9.5

Faux Suede Leather Sz 9.5 Faux Sherpa Lining. Good Pre-Owned Condition , All Man Made Materials Micro Suede Few Scuff Marks And May Need To Be Buffed Out To Clean The Outside, But Still Very Wearable, And Stylish! Inside Has Been Cleaned And Sanitized more

$40.00

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Coach Shoes | Coach Black Leather Chunky Heel Hewes Ankle Booties Size 10 | Color: Black | Size: 10

Coach Shoes | Coach Black Leather Chunky Heel Hewes Ankle Booties Size 10 | Color: Black | Size: 10

Coach Black Leather Chunky Heel Hewes Ankle Booties Size 10. Soft Leather. Slite Scuff On Toe. Heels Soles & Insoles All Have Wear. See All Photos Above. 4 Inch Hunky Heel. Side Zippers. Questions And Offers Welcome. @Nancy20190 more

$55.00

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J. Crew Shoes | J. Crew Black Leather Moto Gold Buckle Low Chunky Heel Ankle Booties | Color: Black/Gold | Size: 6

J. Crew Shoes | J. Crew Black Leather Moto Gold Buckle Low Chunky Heel Ankle Booties | Color: Black/Gold | Size: 6

J.Crew Black Leather Moto Gold Buckle Low Chunky Heel Ankle Booties Adjustable Buckle Detail Size Zipper Closure Gold Accents Almond Shape Toe 2 Inch Chunky Heel Gently Used In Excellent Condition Size 6 more

$75.00

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Free People Shoes | Free People Mccall Black Leather Heel Boots Booties Sz Us 9.5 Eu 40 Ankle Boots | Color: Black | Size: 9.5

Free People Shoes | Free People Mccall Black Leather Heel Boots Booties Sz Us 9.5 Eu 40 Ankle Boots | Color: Black | Size: 9.5

Elevate Your Footwear Game With These Black Leather Ankle Boots From Free People. The Almond Toe Shape And Block Heel Style Make Them Versatile For Any Occasion, Whether It's A Party, Business Meeting, Or Casual Outing. The Layered Accents Add A Unique... more

$49.00

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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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Zara Shoes | Black Boots Ankle Boots Real Leather Block Heeled Booties Size 10 Size 9 | Color: Black | Size: 9

Zara Shoes | Black Boots Ankle Boots Real Leather Block Heeled Booties Size 10 Size 9 | Color: Black | Size: 9

!!! Make A Offer !!! !!! Make A Offer !!! !!! Make A Offer !!! Excellent Condition. *It’s Actually Louie’s Et Ciel, Similar Quality If Not Better Than What’s Listed Here. Only Put Here So More Peoples Can See This Beautiful Pair Of Booties. Real... more

$36.00

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Madewell Shoes | Madewell Pauline Boot In Black Leather Heeled Booties Ankle Boots Size 8 | Color: Black | Size: 8

Madewell Shoes | Madewell Pauline Boot In Black Leather Heeled Booties Ankle Boots Size 8 | Color: Black | Size: 8

Madewell Pauline Boots, Size 8. The Leather On These Is Incredibly Soft And High Quality. Leather Upper, Sole And Lining. Zipper Back. Heel Height Is About 2.5”. Some Marks On Exterior, Sole And Inner Lining, But Overall Good Condition. Madewell Style... more

$49.00

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Madewell Shoes | Madewell Brady Low Cut Brown Ankle Leather Booties Shoe Boot Boots Sz 5 1/2 5.5 | Color: Brown | Size: 5.5

Madewell Shoes | Madewell Brady Low Cut Brown Ankle Leather Booties Shoe Boot Boots Sz 5 1/2 5.5 | Color: Brown | Size: 5.5

Madewell The Brady Bootie. Low Cut Ankle Shoe Boot. Boots Soft Brown Leather. Low Heel. These Have Some Wear And A Small Stain. All Noted In Photos, Reflected In Price. Still Have A Lot Of Wear In Them. Size 5 1/2 5.5 1.72lb more

$65.00

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Zara Shoes | Black Boots Ankle Boots Real Leather Block Heeled Booties Size 10 Size 9 | Color: Black | Size: 9

Zara Shoes | Black Boots Ankle Boots Real Leather Block Heeled Booties Size 10 Size 9 | Color: Black | Size: 9

!!! Make A Offer !!! !!! Make A Offer !!! !!! Make A Offer !!! Excellent Condition. *It’s Actually Louie’s Et Ciel, Similar Quality If Not Better Than What’s Listed Here. Only Put Here So More Peoples Can See This Beautiful Pair Of Booties. Real... more

$36.00

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Zara Shoes | Black Boots Ankle Boots Real Leather Block Heeled Booties Size 10 Size 9 | Color: Black | Size: 9

Zara Shoes | Black Boots Ankle Boots Real Leather Block Heeled Booties Size 10 Size 9 | Color: Black | Size: 9

!!! Make A Offer !!! !!! Make A Offer !!! !!! Make A Offer !!! Excellent Condition. *It’s Actually Louie’s Et Ciel, Similar Quality If Not Better Than What’s Listed Here. Only Put Here So More Peoples Can See This Beautiful Pair Of Booties. Real... more

$36.00

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Coach Shoes | Coach Jemma Soft Calf Ankle Boots Booties Boot | Color: Black | Size: 6

Coach Shoes | Coach Jemma Soft Calf Ankle Boots Booties Boot | Color: Black | Size: 6

Details: Almond-Toe, Side Zip Closure, Topstitched Detail, Back Pull-Tab, Covered Heel, Stacked Heel, Imported, Heel Height 3.5”. Beautifully Preloved W/ Box. Material: Leather Construction/Upper/Lining, & Sole All Dimensions Are Approx. & May Differ... more

$295.00

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Zara Shoes | Black Boots Ankle Boots Real Leather Block Heeled Booties Size 10 Size 9 | Color: Black | Size: 9

Zara Shoes | Black Boots Ankle Boots Real Leather Block Heeled Booties Size 10 Size 9 | Color: Black | Size: 9

!!! Make A Offer !!! !!! Make A Offer !!! !!! Make A Offer !!! Excellent Condition. *It’s Actually Louie’s Et Ciel, Similar Quality If Not Better Than What’s Listed Here. Only Put Here So More Peoples Can See This Beautiful Pair Of Booties. Real... more

$32.00

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Free People Shoes | Free People Sydney Ankle Boots Brown Tan Leather Chunky Heel Lug Sole 39 / 8.5 | Color: Brown/Tan | Size: 8.5

Free People Shoes | Free People Sydney Ankle Boots Brown Tan Leather Chunky Heel Lug Sole 39 / 8.5 | Color: Brown/Tan | Size: 8.5

Excellent Condition Overall, With Some Signs Of Normal Wear. Please Refer To The Photos. Tags: Brown Leather Tan Leather Lace Up Booties more

$63.00

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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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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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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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Free People Shoes | Free People Boots, The James Leather Block Heel Chunky Lug Sole Chelsea Booties | Color: Cream | Size: 7.5

Free People Shoes | Free People Boots, The James Leather Block Heel Chunky Lug Sole Chelsea Booties | Color: Cream | Size: 7.5

Worn 5 Times! No Box, But They Are Like New. I Love Them, But Had Foot Surgery So Only Flats For Me. Booties Feature: Spanish Leather Upper Inside Zipper Closure Leather Lining Cushioned Insole Rubber Outsole Approx. 4.72" Shaft Height Approx. 10"... more

$75.00

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Coach Shoes | Coach Black Leather Boot Giana Stretch Bootie Slip On Chunky Heel Y2k | Color: Black | Size: 9b

Coach Shoes | Coach Black Leather Boot Giana Stretch Bootie Slip On Chunky Heel Y2k | Color: Black | Size: 9b

**Excellent Condition With Minimal Wear And Very Few Scuff Marks Which Are Not Very Noticeable. Please View Pictures For Reference Leather Upper Leather Lining And Footbed Leather Outsole Pull On 3 1/2" Heel Open To Reasonable Offers more

$48.00

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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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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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Madewell Shoes | Chunky Heel Diamond Leather Ankle Boots | Color: Black | Size: 6.5

Madewell Shoes | Chunky Heel Diamond Leather Ankle Boots | Color: Black | Size: 6.5

Size 61/2 Worn Only Twice Good Condition Each Boot Is Missing One Button Ankle Length Chunky Heel Similar To Gucci Chunky Boots more

$23.00

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Anthropologie Shoes | Anthropologie Gracie Leather Ankle Boots Heel Booties Side Zippers Brown 40 | Color: Brown/Tan | Size: 9

Anthropologie Shoes | Anthropologie Gracie Leather Ankle Boots Heel Booties Side Zippers Brown 40 | Color: Brown/Tan | Size: 9

Size 40 Anthropologie Gracie Leather Ankle Boots. Brown Leather Closed Toe Ankle Boots Chunky Heel Booties. Zipper Closure. Gum Sole. more

$45.00

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Anthropologie Shoes | Anthropologie White Leather Chunky Ankle Boot | Color: Black/White | Size: 37eu

Anthropologie Shoes | Anthropologie White Leather Chunky Ankle Boot | Color: Black/White | Size: 37eu

Ivory Leather Outer And Black Leather Inner. Black, Chunky Rubber Heel. Worn Only A Few Times With Very Little Wear And Minor Scuffs. more

$50.00

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Free People Shoes | Free People Belleville Black Cutout Chunky Heel Ankle Boots | Color: Black | Size: 6

Free People Shoes | Free People Belleville Black Cutout Chunky Heel Ankle Boots | Color: Black | Size: 6

Free People Belleville Black Cutout Chunky Heel Ankle Boots Size:36- Which Is A 6 Condition: Slight Wear To The Heels And Bottoms (Please See All Photos) Otherwise Great Preowned! -A Chunky Heel With Wrap Around Buckle And Keyhole Cutout At Side.... more

$40.00

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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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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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Madewell Shoes | Madewell 1937 Billie Boot Ankle Zip Up Sz 9 Olive Green Suede Chunky Heel | Color: Green/Tan | Size: 9

Madewell Shoes | Madewell 1937 Billie Boot Ankle Zip Up Sz 9 Olive Green Suede Chunky Heel | Color: Green/Tan | Size: 9

Madewell 1937 Billie Zip Up Sz 9 Ankle Boot Olive Green Suede Chunky Heel Rich Texture (Suede) And Walkable Stacked Heel Make This Boot A Classic And Favorite. Side Zipper Entry Heel Height 2.5” Leather Lining more

$49.00

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More information about Men's Shoes

Best prices on Dkny ankle boots booties chunky, Leather in Men's Shoes online. Visit Bizrate to find the best deals on top brands. Read reviews on Clothing & Accessories merchants and buy with confidence.