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    Best Seller
    Madewell Shoes | Madewell Ainsley Chelsea Boots | Color: Black | Size: 6

    Madewell Shoes | Madewell Ainsley Chelsea Boots | Color: Black | Size: 6

    Brand New Pair Or Madewell Ainsley Chelsea Boots. Very Comfortable And Leather Stretches Out With Time. I Bought Two Pairs At Full Price Because I Loved Them So Much But These Last. I Don’t Think I Need The Second Pair Since My First One Is Going So... more

    $175.00

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    Madewell Shoes | Madewell Heeled Chelsea Boots Black Size 8 | Color: Black | Size: 8

    Madewell Shoes | Madewell Heeled Chelsea Boots Black Size 8 | Color: Black | Size: 8

    Madewell Heeled Chelsea Boots In Leather Color: True Black Style No: J8307 2 1/2” Heel 7” Total With Shaft. Elastic On Shaft For Easy On & Off! Euc! Has Original Box! Purchased From Nordstrom. Great Bootie For Work Or Going Out! Love The Contrasting... more

    $48.00

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    Best Seller
    Madewell Shoes | Madewell Clog Chelsea Boots | Color: Black | Size: 7

    Madewell Shoes | Madewell Clog Chelsea Boots | Color: Black | Size: 7

    Based On '70s Swedish Clogs, This Retro Bootie Is Handmade Using Traditional Techniques And Set On An Ergonomic Sole Crafted On A Wooden Platform Details: Leather Lining Rubber Sole Good Used Condition, Some Scuffs To Leather And Wood more

    $89.00

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    Madewell Shoes | Madewell Camryn Chelsea Boot In Leather | Color: Brown | Size: 10

    Madewell Shoes | Madewell Camryn Chelsea Boot In Leather | Color: Brown | Size: 10

    Only Worn Twice! Lightweight And Comfy, This Classic Leather Chelsea Boot Has Updated Thick Weather-Sealed Rubber Soles Ready To Take On Whatever The Day Bringsrain Included. Sock-Like Elastic Insets Make Taking These On And Off A Breeze And, Cushiness... more

    $67.00

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    Madewell Shoes | Madewell Ainsley Chelsea Boot In Camel Leather | Color: Brown | Size: 10

    Madewell Shoes | Madewell Ainsley Chelsea Boot In Camel Leather | Color: Brown | Size: 10

    Euc Madewell Ainsley Chelsea Boot In Camel Size 10. Only Worn 3 Times. Small Mark On Front Of One Of The Shoes. Not Noticeable When On Since It Is So Small. Price Reflects This. Super Cute And Comfy! Open To Reasonable Offers more

    $55.00

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    Madewell Shoes | Madewell Marco Chelsea Boot Wooden Heel Black Leather Size 9 | Color: Black/Tan | Size: 9

    Madewell Shoes | Madewell Marco Chelsea Boot Wooden Heel Black Leather Size 9 | Color: Black/Tan | Size: 9

    Madewell Marco Chelsea Boot Wooden Heel Black Leather Part Clog, Part Chelsea, These Comty Pull-On Boots Are Cut At Just The Right Height To Look Cool With Cropped Jeans, Culottes And Skirts. Smooth Leather Upper And Insole. Heel 3.75" Style F5098... more

    $49.00

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    Madewell Shoes | Madewell Grayson Chelsea Boot In Amber Brown Suede Nib | Color: Brown | Size: 8.5

    Madewell Shoes | Madewell Grayson Chelsea Boot In Amber Brown Suede Nib | Color: Brown | Size: 8.5

    Madewell The Grayson Chelsea Boot In Amber Brown. Western Style Boot With A Pointy Toe And Stacked Raw Leather Heel. Leather Lining. Man-Made Sole. New In Box (Purchased Online-Does Not Come With Tags Attached). Please See Photos For Details. Slight... more

    $97.00

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    Madewell Shoes | Madewell Bonham Chelsea Boots | Color: Brown | Size: 6.5

    Madewell Shoes | Madewell Bonham Chelsea Boots | Color: Brown | Size: 6.5

    Madewell Bonham Chelsea Brown Leather Boots. more

    $50.00

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    Madewell Shoes | Madewell Ainsley Chelsea Ankle Pull On Genuine Leather Boot Black Size 7.5 | Color: Black | Size: 7.5

    Madewell Shoes | Madewell Ainsley Chelsea Ankle Pull On Genuine Leather Boot Black Size 7.5 | Color: Black | Size: 7.5

    Madewell Ainsley Chelsea Boots. Black Ankle Pull On Leather Booties In Great Preloved Condition. Still Have Lots Of Life! See Images For Details Of Wear. Genuine Leather Upper, Lining And Sole. 3/4” Heel. Size: 7.5 more

    $50.00

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    Madewell Shoes | Madewell Laura Chelsea Boot In Spotted Calf Hair | Color: Brown | Size: 7

    Madewell Shoes | Madewell Laura Chelsea Boot In Spotted Calf Hair | Color: Brown | Size: 7

    Brand New, I Guess I Took The Tags Off The Bottom. Never Worn. I Have Another Pair In The Same Spotted Calf Hair Pattern And I Don’t Need Two In My Closet., My Loss Is Your Gain. more

    $60.00

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    Madewell Shoes | Madewell Ivy Chelsea Boot Croc Leather Ma428 | Color: Brown | Size: 8

    Madewell Shoes | Madewell Ivy Chelsea Boot Croc Leather Ma428 | Color: Brown | Size: 8

    1/4" Shaft Height Size 8 Run A Bit Small So Would Be Ideal For A Size 7.5 3/4" Heel Embossed Leather Man-Made Sole Brand New more

    $80.00

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    Madewell Shoes | Madewell Frankie Chelsea Boots | Color: Brown | Size: 7

    Madewell Shoes | Madewell Frankie Chelsea Boots | Color: Brown | Size: 7

    Brown Heeled Frankie Chelsea Leather Boots From Madewell. Broken In But In Great Condition. Very Good Condition, Always Got Compliments When I Wore Them. more

    $25.00

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    Madewell Shoes | Madewell Bradley Chelsea Lugsole Boot | Color: Brown | Size: 12

    Madewell Shoes | Madewell Bradley Chelsea Lugsole Boot | Color: Brown | Size: 12

    Madewell Size 12 Chelsea Boot Worn Twice Small Dent In Rubber Near Toe - See Picture 2 Small Water Spots Near Right Heel - See Picture Both Barely Noticeable more

    $50.00

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    Madewell Shoes | Madewell The Ivy Chelsea Boot In Leather | Color: Black/Brown | Size: 7.5

    Madewell Shoes | Madewell The Ivy Chelsea Boot In Leather | Color: Black/Brown | Size: 7.5

    Reposhing This Item I Purchased From @Sarahnwilson. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! more

    $70.00

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    Madewell Shoes | Madewell Carina Chelsea Boot Dark Cabernet | Color: Brown/Red | Size: 8

    Madewell Shoes | Madewell Carina Chelsea Boot Dark Cabernet | Color: Brown/Red | Size: 8

    The Carina Chelsea Style Boots From Madewell With Pull On Tabs. Gorgeous Rich Red Brown Cabernet Color Great For Fall And Winter. These Were Only Available Online And Color Was Listed As "English Saddle Red. A Couple Of Light Scuffs On Back Of Heels,... more

    $70.00

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    Madewell Shoes | Madewell Low Chelsea Booties In Snake Embossed Leather Tan, Beige, Black Size 8 | Color: Black/Tan | Size: 5

    Madewell Shoes | Madewell Low Chelsea Booties In Snake Embossed Leather Tan, Beige, Black Size 8 | Color: Black/Tan | Size: 5

    Madewell Low Chelsea Booties Embossed Snakeskin Print Tan, Beige, Black Size 8 Madewell Leather Chelsea Boots, Heather, Snake - Embossed With Brown Low An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A... more

    $52.00

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    Madewell Shoes | Madewell Ivy Chelsea Leather Boots 7 | Color: Black | Size: 7

    Madewell Shoes | Madewell Ivy Chelsea Leather Boots 7 | Color: Black | Size: 7

    Madewell Ivy Chelsea Leather Boots New Without Tag Made Of Rich Leather Leather Upper Utilitarian Lug Sole Cloudlift Padding For Long Walk On A...Well You Know 5.5" Shaft 3/4 Heel Size: 7 No Original Box more

    $100.00

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    Madewell Shoes | Madewell Ainsley Chelsea Boots In True Black | Color: Black | Size: 8

    Madewell Shoes | Madewell Ainsley Chelsea Boots In True Black | Color: Black | Size: 8

    Reposhing This Item I Purchased From @Chelbel. Loved It, But Ready To Rotate For Something New. Only Wore Once Or Twice So Is Still In Almost Brand New Condition. Questions? Leave A Comment Below! more

    $90.00

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    Madewell Shoes | Madewell Ainsley Chelsea Boots | Color: Brown | Size: 6.5

    Madewell Shoes | Madewell Ainsley Chelsea Boots | Color: Brown | Size: 6.5

    Madewell Ainsley Chelsea Boots. Great Condition- Only Worn A Couple Of Times. more

    $60.00

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    Madewell Shoes | Madewell Ainsley Chelsea Boot In Brown Color Size 7.5 | Color: Brown | Size: 7.5

    Madewell Shoes | Madewell Ainsley Chelsea Boot In Brown Color Size 7.5 | Color: Brown | Size: 7.5

    Pre-Owned Madewell Ainsley Chelsea Boot In Brown Color Size 7.5 Please See Pictures . There Are Small Cracks In The Foot But Still Lots Of Life In These Cute Boots. Price Reflects Condition More Details From Madewell - Crafted From Buttery Leather,... more

    $26.00

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    Madewell Shoes | Madewell | Benning Chelsea Boot - Warm Cinnamon 8.5 New In Box | Color: Brown | Size: 8.5

    Madewell Shoes | Madewell | Benning Chelsea Boot - Warm Cinnamon 8.5 New In Box | Color: Brown | Size: 8.5

    Brand New In Box. Bought These For Myself But They Are Not The Right Size And I Never Got Around To Returning Them. I Wore Them For About 5 Mins In My House. They Are So Beautiful. Super Bummed They Did Not Work For Me. From Website: Coming In... more

    $85.00

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    Madewell Shoes | Madewell Black Chelsea Booties | Color: Black | Size: 9

    Madewell Shoes | Madewell Black Chelsea Booties | Color: Black | Size: 9

    Great Condition Minimal Wear, Fit True To Size more

    $48.00

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    Madewell Shoes | - Madewell Ivy Chelsea Boot In Croc Embossed Leather - Dark Coffee Size 8 | Color: Brown | Size: 8

    Madewell Shoes | - Madewell Ivy Chelsea Boot In Croc Embossed Leather - Dark Coffee Size 8 | Color: Brown | Size: 8

    Madewell Women’s Ivy Chelsea Boots Croc Embossed Leather Brown Size 8 Brand New Without Tags more

    $118.00

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    Madewell Shoes | Madewell Heeled Chelsea Boots In Leather. Size 6. New. Color English Saddle | Color: Brown | Size: 6

    Madewell Shoes | Madewell Heeled Chelsea Boots In Leather. Size 6. New. Color English Saddle | Color: Brown | Size: 6

    Madewell Heeled Chelsea Boots In Leather. Size 6. New. Color English Saddle. Slight Creases From Trying On The Shoes In Store. Never Worn Outside. more

    $120.00

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    Madewell Shoes | Madewell Sonia Chelsea Ankle Bootie Boot Snakeskin 6 | Color: Brown | Size: 6

    Madewell Shoes | Madewell Sonia Chelsea Ankle Bootie Boot Snakeskin 6 | Color: Brown | Size: 6

    Madewell Sonia Chelsea Boot Color: Brown Snakeskin Size 6 Style #M3463 Retail $188 New W/O Box An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. Pull-On Style With... more

    $50.00

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    Madewell Shoes | Madewell The Bradley Chelsea Lugsole Boot Ng679 | Color: Brown/Purple | Size: Various

    Madewell Shoes | Madewell The Bradley Chelsea Lugsole Boot Ng679 | Color: Brown/Purple | Size: Various

    Hit The Streets In This Classic Pull-On Chelsea Boot With Superchunky Lug Soles. The Wide Elastic Gore Not Only Looks Cool, But Also Makes It Easier To Take On And Off. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On... more

    $91.00

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    Madewell Shoes | Madewell Bryce Chelsea Boot Tan Suede Boots | Color: Tan | Size: 8

    Madewell Shoes | Madewell Bryce Chelsea Boot Tan Suede Boots | Color: Tan | Size: 8

    Madewell Bryce Chelsea Boot Tan Suede Boots Pre Owned Good Condition Size 8 Please See All Pics For Best Description Streamlined And Undeniably Cool, This Suede Chelsea Boot Has A A Low-Key Western Vibe We Love. Cuff Up Or Tuck In Your Jeansthese Hit... more

    $49.00

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    Madewell Shoes | Madewell "Carina" Chelsea Boot In Snake Embossed Leather Size: 7m | Color: Brown/Tan | Size: 7

    Madewell Shoes | Madewell "Carina" Chelsea Boot In Snake Embossed Leather Size: 7m | Color: Brown/Tan | Size: 7

    With A Rounded Toe And Stacked Mid-Height Heel That's Perfect For Walking Around In All Day, These Wear-Everywhere Chelsea Boots In Textural Snakeskin-Stamped Leather Have Elastic Goring And A Pull-Tab That Makes On-And-Off A Breeze. Cushiness Alert:... more

    $75.00

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

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

    Madewell The Ivy Chelsea Boot In Leather Women’s Size 8.5 We Toughened Up Classic Chelsea Boots With A Utilitarian Lug Sole. Made Of Rich Leather, They'll Look Cooler And Cooler The More You Wear 'Em. And, Cushiness Alert: Our Mwl Cloudlift Lite... more

    $125.00

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    Madewell Shoes | Madewell Platform Chelsea Boots- Leather And Suede | Color: Brown | Size: 9

    Madewell Shoes | Madewell Platform Chelsea Boots- Leather And Suede | Color: Brown | Size: 9

    Like New! Only Worn A Few Times. Just Can’t Pull These Off! Super High Quality. more

    $110.00

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    Madewell Shoes | Madewell Leather Chelsea Boots | Color: Brown | Size: 7

    Madewell Shoes | Madewell Leather Chelsea Boots | Color: Brown | Size: 7

    A Thin Profile Chelsea Boot By Madewell. They Have Been Regularly Waxed & Oiled And Have Plenty Of Life Left In Them. Still Time For The Soft Leather To Mould To Your Feet! Solid Sole With A Shallow Heel. more

    $60.00

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    Madewell Shoes | Madewell Black Chelsea Heeled Ankle Booties 8.5 | Color: Black | Size: 8.5

    Madewell Shoes | Madewell Black Chelsea Heeled Ankle Booties 8.5 | Color: Black | Size: 8.5

    Madewell Black Heeled Chelsea Boots In Size 8.5. Used But In Good Condition. Very Comfortable Booties That Are Easy To Walk In With A Chunky Heel. more

    $50.00

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    Madewell Shoes | Madewell Camryn Chelsea Boots | Color: Black | Size: 8

    Madewell Shoes | Madewell Camryn Chelsea Boots | Color: Black | Size: 8

    Madewell Camryn Chelsea Boots Great Pre Owned Condition Only Worn A Few Times more

    $75.00

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    Madewell Shoes | Madewell Leather Chelsea Boot | Color: Black | Size: 5

    Madewell Shoes | Madewell Leather Chelsea Boot | Color: Black | Size: 5

    Madewell Chelsea Boot Leather Black Size 5 Open To Reasonable Offers Gently Used - Good Condition Great Addition To Your Boot Rotation Smoke & Pet Free Home more

    $30.00

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    Madewell Shoes | Madewell The Kat Chelsea Suede Chunky Heeled Boot In Chestnut Brown, Size 7.5 | Color: Brown/Tan | Size: 7.5

    Madewell Shoes | Madewell The Kat Chelsea Suede Chunky Heeled Boot In Chestnut Brown, Size 7.5 | Color: Brown/Tan | Size: 7.5

    Excellent Condition - Minimal Signs Of Wear Squared-Off Toe And Chunky Stacked Heel Nicely Cushioned Approx. 4 1/2" Shaft Height Approx. 2 1/2" Heel. Suede Leather Upper Man-Made Sole Top-Rated Seller Same Or Next Day Shipping If You Like The Item But... more

    $75.00

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    Madewell Shoes | Madewell Heeled Chelsea Boots | Color: Brown/Tan | Size: 8

    Madewell Shoes | Madewell Heeled Chelsea Boots | Color: Brown/Tan | Size: 8

    Light Brown / Tan Block Heel Women’s Size 8 Real Leather Good, Used Condition - Some Wear On Heal And A Small Chip (Last Picture) Comment If You Have Any Questions :) more

    $80.00

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    Madewell Shoes | Madewell - Wyckoff Chelsea Lugsole Boot In Leather - Black | Color: Black | Size: 9

    Madewell Shoes | Madewell - Wyckoff Chelsea Lugsole Boot In Leather - Black | Color: Black | Size: 9

    The Wyckoff Chelsea Lugsole Boot In Leather Item Style: Nn020 Size: 9-M Color: True Black Euc - Worn Few Times more

    $100.00

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    Madewell Shoes | Madewell Toasty Chelsea Boot | Color: Tan | Size: 7

    Madewell Shoes | Madewell Toasty Chelsea Boot | Color: Tan | Size: 7

    Brand New! Smoke Free Home. I Needed A Bigger Size. On Sale For $139 On The Website. Originally $178! more

    $90.00

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    Madewell Shoes | Madewell Laura Chelsea Boot Size 7 | Color: Black | Size: 7

    Madewell Shoes | Madewell Laura Chelsea Boot Size 7 | Color: Black | Size: 7

    Madewell Chelsea Boot Size 7 Black Gently Used In Good Condition! Heel Height Is 2 3/4 more

    $75.00

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    Madewell Shoes | Madewell Ivy Chelsea Boot In Bison Leather - Cognac Brown | Color: Brown/Tan | Size: 7

    Madewell Shoes | Madewell Ivy Chelsea Boot In Bison Leather - Cognac Brown | Color: Brown/Tan | Size: 7

    In Good Condition! Some Wear On The Toes Of The Leather. The Soles And Insoles Are In Almost New Condition. In A Beautiful Cognac Color With Multi-Colored Lug Soles. Reasonable Offers Welcome! more

    $80.00

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    More information about Men's Shoes

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