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    Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

    Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

    Reposhing This Item I Purchased From @Cooldudz. Used 1x For A Wedding Rehearsal And Now That I Am Working From Home I Don’t Wear/Need Heels Anymore. Loved Them, Fit Well And Very Stylish. more

    $50.00

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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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    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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    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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    Verona Chelsea Boot - Black - Børn Boots

    Verona Chelsea Boot - Black - Børn Boots

    Women's Børn Verona Chelsea Boot - Black - Ankle boots A chunky platform with sculpted lugs lends street-savvy grounding to this round-toed Chelsea boot crafted from rugged leather. more

    $160.00

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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

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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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    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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    Brandy Block Heel Knee High Boot - Black - Børn Boots

    Brandy Block Heel Knee High Boot - Black - Børn Boots

    Women's Børn Brandy Block Heel Knee High Boot - Black - Knee boots A full-length side zip climbs the minimalist shaft of this leather knee-high boot lifted on a chunky block heel and playfully sculpted treads. more

    $240.00

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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 $30.84

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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 $34.16

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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 5.5)

    Vedolay Men s Oxfords Mens Fashion Leather Wingtip Oxford Dress Boots Casual Mid-Top Ankle Chukka Motorcycle Boot Business Shoes for Men(Black 5.5)

    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

    $33.97 $28.87

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    Verona Chelsea Boot - Brown - Børn Boots

    Verona Chelsea Boot - Brown - Børn Boots

    Women's Børn Verona Chelsea Boot - Brown - Ankle boots A chunky platform with sculpted lugs lends street-savvy grounding to this round-toed Chelsea boot crafted from rugged leather. more

    $160.00

    FREE shipping

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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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    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 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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    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

    $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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    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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    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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    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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    Coach Shoes | Coach Black Urban Hiker Shearling Leather Winter Ankle Boots 6 Chunky Platform | Color: Black | Size: 6

    Coach Shoes | Coach Black Urban Hiker Shearling Leather Winter Ankle Boots 6 Chunky Platform | Color: Black | Size: 6

    Coach Black Urban Hiker Shearling Leather Winter Ankle Boots Size 6b Excellent Preloved Condition Flaws: Slight On Right Toe (See Photos) Lacesless Mid-Top Turnlock Hardware Leather Knot Accent Just Above Heel Leather Upper Padded Shearling Tongue And... more

    $84.00

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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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    J. Crew Shoes | J. Crew Nordic Ankle Boot Faux Fur Shearling Chunky Lace-Up | Color: Black | Size: 6

    J. Crew Shoes | J. Crew Nordic Ankle Boot Faux Fur Shearling Chunky Lace-Up | Color: Black | Size: 6

    J. Crew Retail Classic Hiking Nordic Boot + Added Cozy Faux-Shearling Lining (With Authentic Shearling Cuff) + 2 Sets Of Lacestonal Black & Colorful Red To Brighten Up Your Cold-Weather Outfits. Take That, Winter. Black Size 6 Nubuck Upper Rubber Sole... more

    $115.00

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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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    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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    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

    $19.00

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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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    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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    Madewell Shoes | Madewell Nwot Rosie Ankle Boot Leather Black Size 10 Chunky Heel Zip Side Shoes | Color: Black | Size: 10

    Madewell Shoes | Madewell Nwot Rosie Ankle Boot Leather Black Size 10 Chunky Heel Zip Side Shoes | Color: Black | Size: 10

    New Without Tags, Perfect Black Night Out Boots With A Chunky Heel. Zips Both Work Great, Feet Were Just A Little Too Wide. Never Worn Out, They Were Set On A Slightly Damn Surface To Photograph. more

    $100.00

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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

    $25.00

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    More information about Men's Shoes

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