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    Best Seller
    Anthropologie Shoes | Anthropologie Howsty Sabah Tan Leather Ankle Boots Pointed Toe Western Cowboy | Color: Brown/Tan | Size: 8.5

    Anthropologie Shoes | Anthropologie Howsty Sabah Tan Leather Ankle Boots Pointed Toe Western Cowboy | Color: Brown/Tan | Size: 8.5

    Anthropologie Howsty Boots Eu Size 39 Us Size 8.5/9 Tan 100% Leather Upper Exposed Stitching With Red Details Ankle Height Stretchy Side Panels For Easy On/Off Pointy Toes Good Used Condition Some Wear To Leather Please See Pictures For Most Accurate... more

    $75.00

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    Michael Kors Shoes | Michael Kors Solid Black Leather Pull On Open-Toe Ankle Platform Boots Shooties | Color: Black/Gold | Size: 7.5

    Michael Kors Shoes | Michael Kors Solid Black Leather Pull On Open-Toe Ankle Platform Boots Shooties | Color: Black/Gold | Size: 7.5

    Michael Kors Solid Black Leather Pull On Open-Toe Ankle Boot Euc Buckled Straps Pull On With Elastic Stretch Gore At Ankles Topping Off A Substantial Heel In The Ultra-Chic Shooties From Michael Michael Kors. Michael Michael Kors Pairs Plunging Side... more

    $68.00

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    Best Seller
    Madewell Shoes | Madewell The Western Heeled Ankle Boot Pull On Pointed Toe Leather Suede Sz 7.5 | Color: Cream | Size: 7.5

    Madewell Shoes | Madewell The Western Heeled Ankle Boot Pull On Pointed Toe Leather Suede Sz 7.5 | Color: Cream | Size: 7.5

    With Classic Western Stitching And A Comfy Stacked Heel, This Supple Suede Ankle Boot Is The Cutest (And Goes With Any And Everything). The Pull Tab And Covered Elastic Inserts Make Taking Them On And Off A Total Breeze. Crafted From Smooth Leather... more

    $64.00

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    Thomas and Vine Hanford Plain Toe Chelsea Boot - Red - 9

    Thomas and Vine Hanford Plain Toe Chelsea Boot - Red - 9

    Introducing Hanford by Thomas & Vine, the classic ankle boot designed for convenience and style. Made with genuine leather, these boots are durable and timeless. The 12 mm Tru Comfort Foamâ„¢ insole ensures all-day comfort, while the pull-on chelsea... more

    $129.99

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    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Brown - 10

    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Brown - 10

    Introducing the Tilton ankle boot by Thomas & Vine, a practical and stylish choice for all-day comfort. Made with water-resistant genuine leather, these boots are built to withstand various weather conditions. The 12 mm Tru Comfort Foamâ„¢ insole... more

    $129.99

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    Thomas and Vine Hanford Plain Toe Chelsea Boot - Brown - 10.5

    Thomas and Vine Hanford Plain Toe Chelsea Boot - Brown - 10.5

    Introducing Hanford by Thomas & Vine, the classic ankle boot designed for convenience and style. Made with genuine leather, these boots are durable and timeless. The 12 mm Tru Comfort Foamâ„¢ insole ensures all-day comfort, while the pull-on chelsea... more

    $129.99

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    Free People Shoes | Free People White Jackson West Pointed Toe Block Heel Ankle Boots 39 9 Western | Color: Black/White | Size: 9

    Free People Shoes | Free People White Jackson West Pointed Toe Block Heel Ankle Boots 39 9 Western | Color: Black/White | Size: 9

    In Excellent Preowned Condition Free People Western Booties. Tagged Size 39, Us Size 9. Made Of Portugal. Channel Your Inner Cowgirl Whenever You Slip On This Pair Of Pointed-Toe Boots Crafted From Durable Leather That'll Take You From The Countryside... more

    $120.00

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    Madewell Shoes | - Madewell Chelsea Tan Slip On Ankle Boots Sz 9 | Color: Tan | Size: 9

    Madewell Shoes | - Madewell Chelsea Tan Slip On Ankle Boots Sz 9 | Color: Tan | Size: 9

    Tan Leather With Elastic Stretch On Both Side For Easy Slip On Round Toe Leather Sole Preowned But In Good Condition more

    $65.00

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    Free People Shoes | Free People Atlas Textile Chelsea Ankle Boots | Color: Black/Blue | Size: 38eu

    Free People Shoes | Free People Atlas Textile Chelsea Ankle Boots | Color: Black/Blue | Size: 38eu

    Rounded Toes ~ Ankle Height Shaft ~ Dual/Two Stretchy Gore Panels On The Sides Of The Ankle Shafts ~ Leather Panels On Toes And Heels ... With Scalloped Leather Trims Trimming The Gore/Stretch Panels ~ Woven Textile Panels On Top Of The Foot And On The... more

    $72.00

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    Madewell Shoes | New Madewell The Carina Snake Embossed Leather Low Chelsea Ankle Boots A775 | Color: Cream/Gray | Size: 6

    Madewell Shoes | New Madewell The Carina Snake Embossed Leather Low Chelsea Ankle Boots A775 | Color: Cream/Gray | Size: 6

    New Occasion Business, Casual Calf Width Regular Character Boots Color Multicolor Toe Shape Pointed Toe Closure Pull On Accents Stone Style Chelsea Features Stretch Season Winter, Fall, Spring Shoe Shaft Style Ankle Pattern Animal Print Lining Material... more

    $81.00

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    Free People Shoes | Free People Arlo Ankle Boots | Color: Brown | Size: Various

    Free People Shoes | Free People Arlo Ankle Boots | Color: Brown | Size: Various

    An Essential In Any Boot Collection, These Go-With-Everything Ankle Boots Are Featured In A Shiny Leather And Pull-On Style With Stretchy Elastic Side Accents, Back Zip Closures, And A Classic Round Toe. * Minimal Heel * Cushioned Insole * Durable... more

    $120.00

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    Free People Shoes | Free People Arlo Ankle Boots | Color: Gray/Green | Size: Various

    Free People Shoes | Free People Arlo Ankle Boots | Color: Gray/Green | Size: Various

    An Essential In Any Boot Collection, These Go-With-Everything Ankle Boots Are Featured In A Shiny Leather And Pull-On Style With Stretchy Elastic Side Accents, Back Zip Closures, And A Classic Round Toe. * Minimal Heel * Cushioned Insole * Durable... more

    $130.00

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    Free People Shoes | Free People: Arlo Ankle Boots In Tan | Color: Brown | Size: 7

    Free People Shoes | Free People: Arlo Ankle Boots In Tan | Color: Brown | Size: 7

    Free People Size 37 Us 7m These Go-With-Everything Ankle Boots Are Featured In A Shiny Leather And Pull-On Style With Stretchy Elastic Side Accents, Back Zip Closures, And A Classic Round Toe. Minimal Heel Cushioned Insole Durable Outsole more

    $160.00

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    Free People Shoes | Free People Arlo Ankle Boots | Color: Brown/Tan | Size: 7.5

    Free People Shoes | Free People Arlo Ankle Boots | Color: Brown/Tan | Size: 7.5

    *New Free People Arlo Ankle Boots An Essential In Any Boot Collection, These Go-With-Everything Ankle Boots Are Featured In A Polished Leather And Pull-On Style With Stretchy Elastic Side Accents, Back Zip Closures, And A Classic Round Toe. Minimal... more

    $107.00

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    Madewell Shoes | Madewell Suede Leather Ankle Boots Booties | Color: Red | Size: 8.5

    Madewell Shoes | Madewell Suede Leather Ankle Boots Booties | Color: Red | Size: 8.5

    Coming In Suede With Rounded Toe And Stretchy Gores, These Pull-On Ankle Boots Look Supercute Poking Out From Under Your Jeans Or Paired With Dresses. Plus, Cushiness Alert: With Mwl Cloudlift Lite Padding. 2" Heel. Suede Lining. Leather Lining.... more

    $30.00

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    Free People Shoes | Free People Arlo Ankle Boots | Color: Brown | Size: Various

    Free People Shoes | Free People Arlo Ankle Boots | Color: Brown | Size: Various

    An Essential In Any Boot Collection, These Go-With-Everything Ankle Boots Are Featured In A Shiny Leather And Pull-On Style With Stretchy Elastic Side Accents, Back Zip Closures, And A Classic Round Toe. * Minimal Heel * Cushioned Insole * Durable... more

    $130.00

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    Madewell Shoes | Ankle Boots | Madewell | Color: Black/Cream | Size: 8

    Madewell Shoes | Ankle Boots | Madewell | Color: Black/Cream | Size: 8

    Snakeskin Pattern Short, Ankle Boots With Pointed Toe. Genuine Leather. Elastic Around Ankle For Stretch/Slide-On. Good Condition. Minor Signs Of Wear On Bottoms. Smoke/Pet Free Home. Additional Notes: Runs Small Measurements: Length- 10" Size- Wmns 8... more

    $60.00

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    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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    J. Crew Shoes | J Crew Cognac Brown Chelsea Pull On Boots Ankle Booties Size 8 Eo824 | Color: Brown | Size: 8

    J. Crew Shoes | J Crew Cognac Brown Chelsea Pull On Boots Ankle Booties Size 8 Eo824 | Color: Brown | Size: 8

    J Crew Cognac Brown Leather Chelsea Boots With Stretch Panels For Easy Pull-On. Tag Size 8. Fits 7.5-8 In My Opinion. Style Eo824 Preowned. Shows Signs Of Wear Including Scuffs On Toes, Wear On Back Heels, Wear On Bottoms Of Soles, Creasing In Midfoot... more

    $50.00

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    Michael Kors Shoes | Hamilton Stretch Leather Boot | Color: Brown | Size: 6.5

    Michael Kors Shoes | Hamilton Stretch Leather Boot | Color: Brown | Size: 6.5

    Ankle Boot Vachetta Leather/Stretch Panel 100% Leather Lining: Synthetic Sole: Rubber Almond Toe Zip Fastening Heel Height: 2" Heel Type: Stacked Imported more

    $75.00

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    Free People Shoes | Free People Brooks Lug Sole Boots | Color: Brown | Size: 39

    Free People Shoes | Free People Brooks Lug Sole Boots | Color: Brown | Size: 39

    Deep Wine Leather With An Elastic Detail On Inside And Outside For Stretch And Comfort. Mid Calf Height, And Almond Toe. Extra Chunky Sole Both Fashionable And Perfect For Winter Or Rainy Weather. Good Condition, Some Wear On Toe Crease, And Inside... more

    $65.00

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    Anthropologie Shoes | Cecelia New York Anthropologie Gemma Suede Boots Nib - 8.5 | Color: Brown/Tan | Size: 8.5

    Anthropologie Shoes | Cecelia New York Anthropologie Gemma Suede Boots Nib - 8.5 | Color: Brown/Tan | Size: 8.5

    **New** Cecelia New York Gemma Suede Boots! The Gemma Is The Perfect Bootie For Style And Comfort. A Suede Upper With Elastic Stretch Detail Makes This Boot Slip On Effortlessly. - Size: 8.5 - Color: Nutella / Tan - Almond Toe - Leather Lining - Suede... more

    $79.00

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    Tory Burch Shoes | Brand New Beautiful Tory Burch Simone Over-The-Knee Boots - 10.5 | Color: Black | Size: 10.5

    Tory Burch Shoes | Brand New Beautiful Tory Burch Simone Over-The-Knee Boots - 10.5 | Color: Black | Size: 10.5

    These Are Beautiful! Beautiful! Brand New Never Used Comes With Box And Dust Bag Size 10.5 Retail For $595 Tory Burch Suede Over-The-Knee Boot. Back Zip With Stretch Panel. Flat Stacked Heel. Almond Toe. Leather Lining And Footbed. Leather And Rubber... more

    $515.00

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    Gucci Shoes | Gorgeous Men's Gucci Boots | Color: Black | Size: 11

    Gucci Shoes | Gorgeous Men's Gucci Boots | Color: Black | Size: 11

    Description: - Gucci Leather Ankle Chelsea Boots - Smooth Black Leather - Comfort Stretch Panel - Pull On Loop - Square-Toes - 1" Heel - Lesther Insoles - Tan Soles With "Gucci" Script - Made In Italy Fit: Boots By Gucci Typically Fit True To Size.... more

    $260.00

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    Free People Shoes | Free People Jackson West Leather Boot | Color: Gold | Size: 6

    Free People Shoes | Free People Jackson West Leather Boot | Color: Gold | Size: 6

    Pointed Toe All-Over Textured Leather Construction Stretch-Knit Gored Ankle Panel Zigzagged Stitch Stretch Topline Stacked Block Heel Approx. 4.75” Shaft Height, 8.5” Opening Circumference. Approx. 3.25” Heel Height more

    $129.00

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    Kate Spade Shoes | Euc Kate Spade Leather Boots | Color: Black/Brown | Size: 8.5

    Kate Spade Shoes | Euc Kate Spade Leather Boots | Color: Black/Brown | Size: 8.5

    Kate Spade Boots. Very Versatile Front Panel In Rich Chocolate Brown With Black Stretch Material In Back. Little Leather Bows With Gold Studs On Outside Ankle. Some Scuffs On The Toe Shown In Photos. Very Comfortable Stretch Calf, Low Flat Heel,... more

    $50.00

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    Nine West Shoes | 6 Pair Shoe Lot! Sz 5.5 5 1/2 Nine West, Puma, Etc | Color: Black/Brown | Size: 5.5

    Nine West Shoes | 6 Pair Shoe Lot! Sz 5.5 5 1/2 Nine West, Puma, Etc | Color: Black/Brown | Size: 5.5

    Make An Offer! *For Size Reference My Feet Measure 8.75" From Heel To Toe & Please Ignore The Terrible Polish! Nine West Ankle Boot Cally W 3" Block Heel In Dark Tan Leather. Back Zipper. Worn Once. Minor Scuffs. Ankle Socks Recommended Lifestride Full... more

    $60.00

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    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Black - 9

    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Black - 9

    Introducing the Tilton ankle boot by Thomas & Vine, a practical and stylish choice for all-day comfort. Made with water-resistant genuine leather, these boots are built to withstand various weather conditions. The 12 mm Tru Comfort Foamâ„¢ insole... more

    $129.99

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    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Black - 8.5

    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Black - 8.5

    Introducing the Tilton ankle boot by Thomas & Vine, a practical and stylish choice for all-day comfort. Made with water-resistant genuine leather, these boots are built to withstand various weather conditions. The 12 mm Tru Comfort Foamâ„¢ insole... more

    $129.99

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    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Black - 11

    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Black - 11

    Introducing the Tilton ankle boot by Thomas & Vine, a practical and stylish choice for all-day comfort. Made with water-resistant genuine leather, these boots are built to withstand various weather conditions. The 12 mm Tru Comfort Foamâ„¢ insole... more

    $129.99

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    Thomas and Vine Hanford Plain Toe Chelsea Boot - Red - 10.5

    Thomas and Vine Hanford Plain Toe Chelsea Boot - Red - 10.5

    Introducing Hanford by Thomas & Vine, the classic ankle boot designed for convenience and style. Made with genuine leather, these boots are durable and timeless. The 12 mm Tru Comfort Foamâ„¢ insole ensures all-day comfort, while the pull-on chelsea... more

    $129.99

    go to store
    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Brown - 8.5

    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Brown - 8.5

    Introducing the Tilton ankle boot by Thomas & Vine, a practical and stylish choice for all-day comfort. Made with water-resistant genuine leather, these boots are built to withstand various weather conditions. The 12 mm Tru Comfort Foamâ„¢ insole... more

    $129.99

    go to store
    Thomas and Vine Hanford Plain Toe Chelsea Boot - Red - 9.5

    Thomas and Vine Hanford Plain Toe Chelsea Boot - Red - 9.5

    Introducing Hanford by Thomas & Vine, the classic ankle boot designed for convenience and style. Made with genuine leather, these boots are durable and timeless. The 12 mm Tru Comfort Foamâ„¢ insole ensures all-day comfort, while the pull-on chelsea... more

    $129.99

    go to store
    Thomas and Vine Hanford Plain Toe Chelsea Boot - Red - 8.5

    Thomas and Vine Hanford Plain Toe Chelsea Boot - Red - 8.5

    Introducing Hanford by Thomas & Vine, the classic ankle boot designed for convenience and style. Made with genuine leather, these boots are durable and timeless. The 12 mm Tru Comfort Foamâ„¢ insole ensures all-day comfort, while the pull-on chelsea... more

    $129.99

    go to store
    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Black - 10.5

    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Black - 10.5

    Introducing the Tilton ankle boot by Thomas & Vine, a practical and stylish choice for all-day comfort. Made with water-resistant genuine leather, these boots are built to withstand various weather conditions. The 12 mm Tru Comfort Foamâ„¢ insole... more

    $129.99

    go to store
    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Brown - 11.5

    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Brown - 11.5

    Introducing the Tilton ankle boot by Thomas & Vine, a practical and stylish choice for all-day comfort. Made with water-resistant genuine leather, these boots are built to withstand various weather conditions. The 12 mm Tru Comfort Foamâ„¢ insole... more

    $129.99

    go to store
    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Brown - 9

    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Brown - 9

    Introducing the Tilton ankle boot by Thomas & Vine, a practical and stylish choice for all-day comfort. Made with water-resistant genuine leather, these boots are built to withstand various weather conditions. The 12 mm Tru Comfort Foamâ„¢ insole... more

    $129.99

    go to store
    Thomas and Vine Hanford Plain Toe Chelsea Boot - Black - 10

    Thomas and Vine Hanford Plain Toe Chelsea Boot - Black - 10

    Introducing Hanford by Thomas & Vine, the classic ankle boot designed for convenience and style. Made with genuine leather, these boots are durable and timeless. The 12 mm Tru Comfort Foamâ„¢ insole ensures all-day comfort, while the pull-on chelsea... more

    $129.99

    go to store
    Thomas and Vine Hanford Plain Toe Chelsea Boot - Black - 9.5

    Thomas and Vine Hanford Plain Toe Chelsea Boot - Black - 9.5

    Introducing Hanford by Thomas & Vine, the classic ankle boot designed for convenience and style. Made with genuine leather, these boots are durable and timeless. The 12 mm Tru Comfort Foamâ„¢ insole ensures all-day comfort, while the pull-on chelsea... more

    $129.99

    go to store
    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Black - 10

    Thomas and Vine Water Resistant Plain Toe Chelsea Boot - Black - 10

    Introducing the Tilton ankle boot by Thomas & Vine, a practical and stylish choice for all-day comfort. Made with water-resistant genuine leather, these boots are built to withstand various weather conditions. The 12 mm Tru Comfort Foamâ„¢ insole... more

    $129.99

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    More information about Men's Shoes

    Best prices on Almond toe ankle boots natural, Leather, Stretchable 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.