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    Best Seller
    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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    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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    Best Seller
    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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    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 13

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 13

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

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    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 8.5

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 8.5

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

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    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 10.5

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 10.5

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

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    Free People Shoes | Free People Arlo Santa Fe Ankle Chelsea Boots Black Crocodile Snake Size 7 | Color: Black | Size: 7

    Free People Shoes | Free People Arlo Santa Fe Ankle Chelsea Boots Black Crocodile Snake Size 7 | Color: Black | Size: 7

    Free People Arlo Santa Fe Ankle Boots Size: European 37.5 (Us 7) Color: Black Crocodile Basically Brand New. Sales Sticker Still On Sole. Only Worn Once. Condition: These Shoes Are Intentionally Distressed. Brand New, They Intentionally Look Worn In,... more

    $80.00

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    Free People Shoes | Black Free People Ankle Chelsea Boot | Color: Black | Size: 8

    Free People Shoes | Black Free People Ankle Chelsea Boot | Color: Black | Size: 8

    There Are A Euro Size 41 (Us 8) Free People Cowboy/ Chelsea Boot Style Stretchy On The Side Like A Chelsea Boot Small Heel more

    $45.00

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    Free People Shoes | Free People Chelsea Textile Atlas Boots Blue Kilm Western Ankle Scallop 40 | Color: Blue | Size: 40eu

    Free People Shoes | Free People Chelsea Textile Atlas Boots Blue Kilm Western Ankle Scallop 40 | Color: Blue | Size: 40eu

    Excellent Condition ... No Flaws!! Bundle And Save 20%... Free Shipping On All Bundles! ~ Offers Welcome! ~ Fast Shipping! ~ For Offers European Size 40 Appreciate Your Wonderful Sense Of Style And Make A Statement In These Jaw-Dropping Chelsea Boots... more

    $98.00

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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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    Anthropologie Shoes | Anthropologie Sixtyseven Distressed Croc Leather Boho Chelsea Ankle Boots | Color: Black | Size: 37eu

    Anthropologie Shoes | Anthropologie Sixtyseven Distressed Croc Leather Boho Chelsea Ankle Boots | Color: Black | Size: 37eu

    Great Used Condition. Distressed Croc Chelsea Ankle Boots By Anthropologie Brand Sixtyseven In Black. Chic, Edgy Aesthetic, A Versatile Capsule Wardrobe Piece For The Season That Can Be Dressed Up Or Worn Casually. Slip-On Ankle Boots With Textured... more

    $50.00

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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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    Nine West Shoes | Nib Nine West Navy Suede Cap Toe Stretch Fabric Ankle Boot 9m | Color: Blue | Size: 9

    Nine West Shoes | Nib Nine West Navy Suede Cap Toe Stretch Fabric Ankle Boot 9m | Color: Blue | Size: 9

    Super Cute Navy Blue Textile Fabric Ankle Boot With Faux Satin Tie Front By Nine West Suede Cap Toe Balance Textile Fabric With Stain Tie Accent Approx. 3.5" Wrapped Cylinder Heel. Lightly Padded Footbed. All Items Ship From Smoke And Pet Free Home.... more

    $59.00

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    Madewell Shoes | Madewell Ainsley Chelsea Boot - Size 7.5 | Color: Black | Size: 7.5

    Madewell Shoes | Madewell Ainsley Chelsea Boot - Size 7.5 | Color: Black | Size: 7.5

    Madewell Leather Ankle Boots Gently Worn Elastic Stretch On Interior And Exterior Side Ankle Minor Scuffing On Left Shoe Shown In Photo more

    $47.00

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    Coach Shoes | Coach Bowery Beadchain Chelsea Boots Black - 8 | Color: Black | Size: 8

    Coach Shoes | Coach Bowery Beadchain Chelsea Boots Black - 8 | Color: Black | Size: 8

    Gorgeous Bowery Beadchain Chelsea Boots From Coach. Black Leather With Beadchain Detailing Around The Ankle. Pull On Style With Stretch Panels For A Comfortable Fit. Essential Style For Every Day Wear. New In Box. Size 8b more

    $125.00

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    Free People Shoes | Free People Brooks Lug Sole Chelsea Boots | Color: Cream | Size: 10

    Free People Shoes | Free People Brooks Lug Sole Chelsea Boots | Color: Cream | Size: 10

    A Contemporary Spin On The Classic Chelsea Style, These Timeless Ankle-Covering Boots Feature A Chunky Sole For An Exaggerated Look. A Neutral Boot To Pop Any Outfit Fp Collection Color Chalk Artisan Crafted From Fine Leathers And Premium Materials, Fp... more

    $25.00

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    Free People Shoes | Free People Brooks Lug Sole Chelsea Boot | Color: Black | Size: 8

    Free People Shoes | Free People Brooks Lug Sole Chelsea Boot | Color: Black | Size: 8

    Free People Brooks Lug Sole Chelsea Boot In Good Pre Owned Condition. Some Parts Can Use A Brushing As Can Be Expected With Suede. Some Very Minimal Creasing On Ankle Part. Please See All Pictures For Wear. Minor Wear On Soles. Features A Super-Chunky... more

    $105.00

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    Free People Shoes | Free People White James Chunky Chelsea Boots 40 | Color: White | Size: 10

    Free People Shoes | Free People White James Chunky Chelsea Boots 40 | Color: White | Size: 10

    Nib Free People James Chelsea Ankle Boots Side Zip Closure Stretch Side Panels For Easy On Cushion Footbed Color Is White But Looks More Like A Cream Color Leather Uppers 6” Shaft Height 3.5” Chunky Heel 1” Platform more

    $85.00

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    J. Crew Shoes | J. Crew Willa Stacked Heel Leather Chelsea Boots, Black, 9 | Color: Black | Size: 9

    J. Crew Shoes | J. Crew Willa Stacked Heel Leather Chelsea Boots, Black, 9 | Color: Black | Size: 9

    These Refined Leather Ankle Boots Have A High Shaft That Looks Extra-Cool Peeking Out From The Hem Of A Midi Skirt Or Your Favorite Straight- Leg Jeans. Detail We Love: Stretchy Side Panels Make Them Easier To Take On And Off. Leather Upper And Lining.... more

    $50.00

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    Free People Shoes | Free People Nwt Arlo Santa Fe Chelsea Boot Croc Embossed Leather Cognac Brown | Color: Brown | Size: 8

    Free People Shoes | Free People Nwt Arlo Santa Fe Chelsea Boot Croc Embossed Leather Cognac Brown | Color: Brown | Size: 8

    Free People Nwt Arlo Santa Fe Chelsea Boot Croc Embossed Leather Cognac Brown Size 8 Nwt From Marshall’s Cognac Brown Caramel Embossed Leather Upper Croc Back Zipper Closure Approx 1.5” Heel Stretchy Top Half Mixed Media Ankle Length more

    $100.00

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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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    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Black - 7.5

    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Black - 7.5

    The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more

    $69.99

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    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 11

    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 11

    The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more

    $69.99

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    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 8.5

    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 8.5

    The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more

    $69.99

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    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Blue - 9.5

    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Blue - 9.5

    The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more

    $69.99

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    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 11

    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 11

    The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more

    $69.99

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    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 10.5

    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 10.5

    The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more

    $69.99

    go to store
    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 10

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 10

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

    go to store
    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 13

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 13

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

    go to store
    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 9.5

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 9.5

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

    go to store
    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 9

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 9

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

    go to store
    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 8

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 8

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

    go to store
    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 12

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Brown - 12

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

    go to store
    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Grey - 12

    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Grey - 12

    The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more

    $69.99

    go to store
    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 10.5

    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 10.5

    The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more

    $69.99

    go to store
    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 10

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 10

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

    go to store
    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 14

    Vance Co. Shoes Hogan Wingtip Chelsea Boot - Black - 14

    Introducing the Hogan ankle boot by Vance Co. Crafted with premium vegan leather, these boots offer both style and comfort. Featuring a convenient pull-on design with chelsea stretch gore, they are easy to slip on and off. With a 12 mm Tru Comfort... more

    $79.99

    go to store
    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 10

    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 10

    The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more

    $69.99

    go to store
    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 8

    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Brown - 8

    The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more

    $69.99

    go to store
    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Blue - 9

    Vance Co. Shoes Vance Co. Men's Wide Width Landon Chelsea Dress Boot - Blue - 9

    The wide-width Chelsea dress boot by Vance Co. features premium faux leather uppers that rise to the ankles with subtle top-stitching bordering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. Heel... more

    $69.99

    go to store

    More information about Men's Shoes

    Best prices on Old navy ankle boots chelsea, Stretchable, Shoes 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.