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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 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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    Best Seller
    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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    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

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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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    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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    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 | Madewell The Spencer Chelsea Leather Ankle Boots | Color: Tan | Size: 9.5

    Madewell Shoes | Madewell The Spencer Chelsea Leather Ankle Boots | Color: Tan | Size: 9.5

    Madewell 9.5 Spencer Short Chelsea Boot Style C1375 Mink Taupe Tan Color Stacked Heel No Original Box Slight Marks In Leather (See Photos) Excellent Used Condition 1.75" Heel Almond Toe Luxe Quality Stretch On Both Sides Offers Welcome. No Trades. more

    $36.00

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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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    Madewell Shoes | Nib Madewell Lugsole Chelsea Boots 6.5 | Color: Brown/Tan | Size: 6.5

    Madewell Shoes | Nib Madewell Lugsole Chelsea Boots 6.5 | Color: Brown/Tan | Size: 6.5

    Nib Great Gift But Not My Style. There Is A Blemish On Right Boot- See Photo/Video. From Madewell Website: With Stretch Gores, A Chunky Platform And Stacked Heel, These Suede Ankle Boots Are The Best Of Both Worldscomfy And Cool. Plus, Our Mwl... more

    $100.00

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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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    Madewell Shoes | Madewell Size 9.5 Wyckoff Chelsea Lugsole Boots In Chocolate Raisin | Color: Brown | Size: 9.5

    Madewell Shoes | Madewell Size 9.5 Wyckoff Chelsea Lugsole Boots In Chocolate Raisin | Color: Brown | Size: 9.5

    Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. When You Select Your... more

    $130.00

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    Madewell Shoes | Madewell Ainsley Chelsea Boot In Metallic | Color: Gold | Size: 7

    Madewell Shoes | Madewell Ainsley Chelsea Boot In Metallic | Color: Gold | Size: 7

    Like New Madwell Ainsley Chelsea Boot Gently Worn - Minor Scuffing Crafted From Metallic Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: We've Added An Extra Layer Of Padding To Make Them... more

    $50.00

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    Kate Spade Shoes | Kate Spade Chelsea Rain Boot | Color: Black/Gold | Size: 8

    Kate Spade Shoes | Kate Spade Chelsea Rain Boot | Color: Black/Gold | Size: 8

    Excellent Condition, Very Gently Used Rain Boot By Kate Spade. These Are Black And Gold With Cute Spade/Bow On Back. Minimal Wear To Soles. I Just Never Worn Them. Stretch Side For Easy On And Off. more

    $65.00

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

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

    Love These Boots, But Only Wore Twice - They’re Too Narrow For My Feet In This Size.* Both Casual And Stylish Leather Booties, With Cloudlift Lite Padding. *They Run Narrow, But Will Stretch With Wear. Go Up A Size If You Have A Wider Foot Or Want To... more

    $90.00

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    Madewell Shoes | Madewell The Ainsley Chelsea Boot J8295 Leather | Color: Black | Size: Various

    Madewell Shoes | Madewell The Ainsley Chelsea Boot J8295 Leather | Color: Black | Size: Various

    Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: We've Added An Extra Layer Of Padding To Make Them Even Easier On The Feet. Logo On Sole Marked To Prevent Retail Store... more

    $62.00

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    Madewell Shoes | Madewell Ainsley Chelsea Boot Nwt | Color: Tan | Size: 8.5

    Madewell Shoes | Madewell Ainsley Chelsea Boot Nwt | Color: Tan | Size: 8.5

    Nib! Realized I Bought A Backup Pair That I Never Wore Def Takes A Bit To Break In But End Up So Comfortable “Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: Our Mwl... more

    $120.00

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    J. Crew Shoes | J. Crew Pull-On Chelsea Suede Boots In Desert Sand | Color: Black/Tan | Size: 9

    J. Crew Shoes | J. Crew Pull-On Chelsea Suede Boots In Desert Sand | Color: Black/Tan | Size: 9

    J. Crew Pull-On Chelsea Suede Boots In Desert Sand Feature A Leather Lining, Soft Suede With A Stretchy Side Panel, Just Pull 'Em On And Go! You'll Want To Reach For Our Easy Oh-So-Walkable Chelsea Boots Everyday. Item Does Not Include The Original Box. more

    $150.00

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    Madewell Shoes | Madewell The Ainsley Chelsea Boot In Black Size 8.5 | Color: Black | Size: 8.5

    Madewell Shoes | Madewell The Ainsley Chelsea Boot In Black Size 8.5 | Color: Black | Size: 8.5

    Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Please Note: The Manufacturer Comments That These Boots Fit Narrow But Will Stretch With Wear Recommending Going Up A Size If You Have A... more

    $50.00

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    Madewell Shoes | Madewell The Benning Chelsea Boot In True Black Leather | Color: Black | Size: Various

    Madewell Shoes | Madewell The Benning Chelsea Boot In True Black Leather | Color: Black | Size: Various

    Listing As Pre-Owned. Excellent Condition. Line On Inside Label To Prevent In Store Returns. Color: True Black Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. And, Cushiness Alert: Our Mwl Cloudlift Lite... more

    $98.00

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    Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Brown/Tan | Size: 7

    Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Brown/Tan | Size: 7

    Moving Soon So I Really Need To Clear Out The Closet! Gently Worn Madewell Boots In Cognac Color. Totally Love These Boots But I Am Never Reaching For Them These Days. From Madewell: Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared... more

    $50.00

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    Madewell Shoes | Madewell Raegan Tan Genuine Leather Slip On Chelsea Boots Sz 8 | Color: Tan | Size: 8

    Madewell Shoes | Madewell Raegan Tan Genuine Leather Slip On Chelsea Boots Sz 8 | Color: Tan | Size: 8

    Brand / Info Madewell. Genuine Leather, Tan Color. Slip On Style With Stretchy Sides. Has Pulls At Achilles Tendon To Easily Slip Shoes On. Leather Upper. Leather Lining. Synthetic Sole. Made In Brazil. Style # J8307 Size / Feels Like 8, True To Size... more

    $61.00

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    Free People Shoes | Free People James Chelsea Mustard Yellow Suede Platform Boots Size 39 | Color: Black/Yellow | Size: 8.5

    Free People Shoes | Free People James Chelsea Mustard Yellow Suede Platform Boots Size 39 | Color: Black/Yellow | Size: 8.5

    Free People James Chelsea Mustard Yellow Suede Platform Boots Size 39 (Us Size 8.5) *Good Used Condition : See Photos For Minimal Signs Of Wear : Couple Small Spots Side Of One Of The Boots. *Quality Leather Upper With Black Stretch *Pretty Color :... more

    $80.00

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    Coach Shoes | Coach Elijah Chelsea Boots | Color: Red | Size: 8

    Coach Shoes | Coach Elijah Chelsea Boots | Color: Red | Size: 8

    Coach Elijah Chelsea Boots In Good Used Condition. Has Creases From Normal Wear. Polished Calf Leather Gives This Tomboyish Boot A Rich Sheen, While The Saddle-Colored Stripe On The Sole Is A Nod To Heritage Coach(Tm) Craftsmanship. Fashion Meets... more

    $95.00

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    Madewell Shoes | Https://Www.Madewell.Com/The-Benning-Chelsea-Boot-Nn017.Html | Color: Brown | Size: 9

    Madewell Shoes | Https://Www.Madewell.Com/The-Benning-Chelsea-Boot-Nn017.Html | Color: Brown | Size: 9

    Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. Leather Upper. Leather Lining. Man-Made Sole. Do Well:... more

    $80.00

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    Madewell Shoes | Madewell $198 The Wyckoff Chelsea Lugsole Boot Chocolate Leather Size 11 Nn020 | Color: Brown | Size: 11

    Madewell Shoes | Madewell $198 The Wyckoff Chelsea Lugsole Boot Chocolate Leather Size 11 Nn020 | Color: Brown | Size: 11

    Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know.6" Shaft Height1 1/2"... more

    $78.00

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    Madewell Shoes | Madewell The Bradley Chelsea Lugsole Boots - Size: 7.5 | Color: Black | Size: 7.5

    Madewell Shoes | Madewell The Bradley Chelsea Lugsole Boots - Size: 7.5 | Color: Black | Size: 7.5

    New Without Tags - No Call-Outs Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert 6" Shaft Height (Based On Size 7). 1 1/2" Heel Height. Leather... more

    $149.00

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    Madewell Shoes | Madewell Laura Chelsea Real Fur Dyed Spotted Calf Hair Hilty Block Boots Size 7 | Color: Brown/Tan | Size: 7

    Madewell Shoes | Madewell Laura Chelsea Real Fur Dyed Spotted Calf Hair Hilty Block Boots Size 7 | Color: Brown/Tan | Size: 7

    Madewell Laura Chelsea Real Fur Dyed Spotted Calf Hair Hilty Block Boots Size 7 Brand: Madewell Size: 7 Color: Tan And Brown Pattern: Leopard Material: Leather Condition: Preloved, In Good Condition, Stretch Band Shows Minimal Features: Slip On Closure... more

    $125.00

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    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boots Nn020 9 | Color: Black/White | Size: 9

    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boots Nn020 9 | Color: Black/White | Size: 9

    Ready For All Your Supercute Fall Fits, These Leather Chelsea Boots Have Stretchy Gores And Wear-All-Day-Everywhere Chunky Lugsoles. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. 6" Shaft Height (Based... more

    $134.00

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    Tory Burch Shoes | Excellent Condition Clean Tory Burch Expedition Chelsea Boot Size 8.5 | Color: Black | Size: 8.5

    Tory Burch Shoes | Excellent Condition Clean Tory Burch Expedition Chelsea Boot Size 8.5 | Color: Black | Size: 8.5

    Worn One Time! Clean!! Like New Can Even Tell They Were Worn. Runs True To Size, No Need To Size Up On This One. Super Comfy! A Rubber Toe Caps Off This Expedition-Seeking Leather Boot Crafted With Stretchy Side Goring And Balanced On A Block Heel For... more

    $300.00

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

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

    Madewell Ainsley Chelsea Boot - Black Size 7.5 Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know.... more

    $40.00

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    Madewell Shoes | Madewell Spencer Leather Short Chelsea Tan Boot Size 7.5 | Color: Tan | Size: 7.5

    Madewell Shoes | Madewell Spencer Leather Short Chelsea Tan Boot Size 7.5 | Color: Tan | Size: 7.5

    The Madewell Spencer Short Chelsea Boot Is A Size 7.5 In A Mink Taupe Tan Color With A Stacked 1.75" Heel And Almond Toe. The Boot Features Luxe Designer Quality And Elastic Stretch On Both Sides For A Pull-On Style. Made Of Leather Upper Please Note... more

    $40.00

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    More information about Men's Shoes

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