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Penny Loafer Ankle Boots

Penny Loafer Ankle Boots

Men's Thom Browne Penny Loafer Ankle Boots - Black - Casual boots 100% Calfskin Leather, 100% Rubber. Made in Italy. more

$1,229.00 $707.90

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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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Best Seller
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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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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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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Marsh Check Textured Ankle Boot

Marsh Check Textured Ankle Boot

Men's Burberry Marsh Check Textured Ankle Boot - Gray - Casual boots Give your rainy-day look a pop of pizzazz with this check-patterned, transparent ankle boot textured with diamond embossing and set on a chunky lug sole. 1 1/2" heel, 38mm, 5" shaft,... more

$870.00

FREE shipping

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Prisilla Pointed Toe Zip Bootie - Black - Aquatalia Boots

Prisilla Pointed Toe Zip Bootie - Black - Aquatalia Boots

Women's Aquatalia Prisilla Pointed Toe Zip Bootie - Black - Ankle boots Streamlined design showcases the rich leather wrapping this water-repellent pointy-toe bootie finished with a handy side zip and low heel. 4 1/2" shaft Water-repellent Leather... more

$495.00 $347.00

FREE shipping

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Larra Weatherproof Bootie - Black - Aquatalia Boots

Larra Weatherproof Bootie - Black - Aquatalia Boots

Women's Aquatalia Larra Weatherproof Bootie - Black - Ankle boots A squared-off toe and wrapped block heel balance a creamy suede bootie featuring a signature fuss-free water-repellent finish. 2" heel; 5 1/2" shaft Leather upper/Leather and Textile... more

$395.00 $158.00

FREE shipping

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Free People Shoes | Free People || Chunky Platform Chain Link Ankle Strap Loafers | Color: Black/Gold | Size: 38eu

Free People Shoes | Free People || Chunky Platform Chain Link Ankle Strap Loafers | Color: Black/Gold | Size: 38eu

These Shoes Are So Adorable With Gold Tone Detail On The Front Chunky Lug Soul With A Cute Wraparound Ankle Strap. I Just Don’t Wear Them Enough And Need To Make Room In My Closet. Worn Twice. Super Cute With A Wide Leg Pant No Damage. Loafers Meets... more

$45.00

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American Eagle Outfitters Shoes | American Eagle Leather Suede Ankle Boots Chukka Boots Loafers Grey Size 8 | Color: Gray | Size: 8

American Eagle Outfitters Shoes | American Eagle Leather Suede Ankle Boots Chukka Boots Loafers Grey Size 8 | Color: Gray | Size: 8

American Eagle Leather Suede Ankle Boots Chukka Boots Loafers Grey Size 8 Gently Used more

$25.00

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Free People Shoes | Free People Madison Loafer Chunky Lug Sole Zipper Boots Green Eu 40 Us 10 | Color: Green | Size: 10

Free People Shoes | Free People Madison Loafer Chunky Lug Sole Zipper Boots Green Eu 40 Us 10 | Color: Green | Size: 10

Free People Madison Loafer Chunky Lug Sole Zipper Boots Green Eu 40 Us 10 Brand :Free People Style: Madison Chunky Boot Color: Green Size : 40 Us 10 Sku No : 8522 Condition : New Without Tag more

$120.00

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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

$72.00

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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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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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Free People Shoes | Free People Dylan Lug Boots Combat Eu/36 Us/6 Black Suede Leather Chunky Ankle | Color: Black | Size: 6

Free People Shoes | Free People Dylan Lug Boots Combat Eu/36 Us/6 Black Suede Leather Chunky Ankle | Color: Black | Size: 6

This Is A Pair Of Free People Dylan Black Suede Leather Chunky Lug Ankle Combat Boots. Lace Up Design With Side Zip Closure. Block Heel. Made In Spain. Leather Upper Lining And Insole. Rubber Outsole. Women’s Size Eu 36 And Us Size 6. Heel 3.5”.... more

$85.00

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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 | Madewell The Ames Boot Chunky Heel Leather Ankle Booties In Cognac Size 8 | Color: Brown/Red | Size: 8

Madewell Shoes | Madewell The Ames Boot Chunky Heel Leather Ankle Booties In Cognac Size 8 | Color: Brown/Red | Size: 8

Chunky Stacked Heel. Rich Soft Leather. Even Better With Age. Leather Upper. 4 1/4" Shaft Height 10 1/2" Shaft Circumference 3" Heel Leather Lining Man-Made Sole Import Style #B2061 Size 8 Please Note: I Have Personally Taken All Of These Photos... more

$150.00

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American Eagle Outfitters Shoes | 7.5 American Eagle Tan Fringe Side Low Chunky Heel Bootie Ankle Boot Shoes | Color: Brown/Tan | Size: 7.5

American Eagle Outfitters Shoes | 7.5 American Eagle Tan Fringe Side Low Chunky Heel Bootie Ankle Boot Shoes | Color: Brown/Tan | Size: 7.5

Good Used Condition Women's 7.5 American Eagle Tan Fringe Side Low Chunky Heel Booties Ankle Boots Shoes Fabric Upper/Manmade Material Approx 1.75"-2" Heel Approx 3"-3.25" Heel To Top Color Hue Might Vary Due To Lighting Conditions Thanks For Looking... more

$28.00

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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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Free People Shoes | Free People Mara Zip Moto Combat Chunky Ankle Zipper Edgy Boots 36 | Color: Purple | Size: 6

Free People Shoes | Free People Mara Zip Moto Combat Chunky Ankle Zipper Edgy Boots 36 | Color: Purple | Size: 6

New With Box Turn Heads In These So Cool And Unique Boots Featured In A Slim Silhouette And Ankle Style With A Bold Rounded, Chunky Sole, Side Zipper Closures, And Heel Loop Detailing. Pull-On Style Round Toe Durable Rubber Outsole Care/Import Made In... more

$278.00

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Urban Outfitters Shoes | Arts Thread X Urban Outfitters Black Make It Fringe Platform Chunky Ankle Boots | Color: Black | Size: 8

Urban Outfitters Shoes | Arts Thread X Urban Outfitters Black Make It Fringe Platform Chunky Ankle Boots | Color: Black | Size: 8

Reposhing! I Wore These Once, They're In The Same Condition As Listed Originally. Comes From A Smoke Free And Pet Free Home. Og Posting Info: Arts Thread X Urban Outfitters Black Make It Fringe Platform Chunky Ankle Boots Size 8 Great Pre-Used... more

$27.00

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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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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 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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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

$99.00

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Free People Shoes | Free People Nicola Chunky Block Heel Suede Ankle Boots Size 41 | Color: Tan | Size: 41

Free People Shoes | Free People Nicola Chunky Block Heel Suede Ankle Boots Size 41 | Color: Tan | Size: 41

Free People Nicola Chunky Heel Boho Boot Sz 41 Tan Color Reptile Texture Print Inside Zipper Closure Chunky Block Heel Excellent Pre Own Condition Some Marks Shown On Pictures more

$64.00

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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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Zara Shoes | Black Chunky Ankle Boots | Color: Black | Size: 9

Zara Shoes | Black Chunky Ankle Boots | Color: Black | Size: 9

Pull On Sweater Boots From Zara. Super Cute With Jeans Or Dress Pants. I Work From Home Now So No Needs For 30 Pairs Of Black Boots! more

$30.00

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Nine West Shoes | Gorgeous Like Knew Suede Ankle Boot Lace Up Chunky Heel | Color: Black | Size: 6.5

Nine West Shoes | Gorgeous Like Knew Suede Ankle Boot Lace Up Chunky Heel | Color: Black | Size: 6.5

White Stitching Gorgeous 2 Inch Heel more

$65.00

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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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Madewell Shoes | New Katie Croc Embossed Back Zip Ankle Boots From Madewell 6.5 2” Chunky Heel | Color: Brown | Size: 6.5

Madewell Shoes | New Katie Croc Embossed Back Zip Ankle Boots From Madewell 6.5 2” Chunky Heel | Color: Brown | Size: 6.5

The Katie Espresso Brown Ankle Boot From Madewell Features Croc Embossed Leather Uppers, Back Zipper, And 2” Chunky Heel. Rubber Lug Outsole For Secure Footing. New Without The Tag In A Size 6.5, Retail Price $195.. more

$60.00

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Free People Shoes | Free People Marquis Brown Suede Leather Chunky Heel Ankle Boots Sz 41/Us 11 | Color: Brown | Size: 11

Free People Shoes | Free People Marquis Brown Suede Leather Chunky Heel Ankle Boots Sz 41/Us 11 | Color: Brown | Size: 11

Good Used Condition. Beautiful Leather Uppers And Solid Heel. Light Wear As Indicated In Pictures. more

$40.00

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