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    Best Seller
    Madewell Shoes | Madewell Glenda Platform Boot In Suede | Color: Tan | Size: 7.5

    Madewell Shoes | Madewell Glenda Platform Boot In Suede | Color: Tan | Size: 7.5

    Brand New, Never Worn! With Stretch Gores, A Chunky Platform And Stacked Heel, These Suede Ankle Boots Are The Best Of Both Worldscomfy And Cool. Plus, Our Mwl Cloudlift Lite Padding Makes It Feel Like You're Walking On A...Well, You Know. 2 3/4" Heel.... more

    $75.00

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    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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    Best Seller
    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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    Madewell Shoes | Madewell Like New The Chelsea Rain Boot | Color: Black | Size: 5

    Madewell Shoes | Madewell Like New The Chelsea Rain Boot | Color: Black | Size: 5

    Madewell Like New The Chelsea Rain Boot Like New Condition No Box Rudder Boot Chelsea Style Stretch Sides Black Size 5 more

    $45.00

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    Madewell Shoes | - Madewell The Wyckoff Chelsea Lugsole Boot Nn020 Worn Once Chocolate Raisin | Color: Brown | Size: Various

    Madewell Shoes | - Madewell The Wyckoff Chelsea Lugsole Boot Nn020 Worn Once Chocolate Raisin | Color: Brown | Size: Various

    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

    $78.00

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    Madewell Shoes | Madewell $188 The Benning Chelsea Boot Warm Cinnamon Size 12 Nn017 | Color: Brown | Size: 12

    Madewell Shoes | Madewell $188 The Benning Chelsea Boot Warm Cinnamon Size 12 Nn017 | Color: Brown | Size: 12

    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.5 1/4" Shaft Height Leather Upper.Leather Lining.Man-Made... more

    $108.00

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    Madewell Shoes | Madewell The Benning Chelsea Black Leather Boot | Color: Black | Size: 6

    Madewell Shoes | Madewell The Benning Chelsea Black Leather Boot | Color: Black | Size: 6

    Black Super-Soft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. 5 1/4" Shaft Height. Leather Upper. Leather Lining. Man-Made Sole. more

    $85.00

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    Madewell Shoes | Madewell Wyckoff Chelsea Lugsole Boot | Color: Black | Size: Various

    Madewell Shoes | Madewell Wyckoff Chelsea Lugsole Boot | Color: Black | Size: Various

    “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. 1 1/2" Heel Height.... more

    $150.00

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    Madewell Shoes | Madewell Gwenda Platform Ankle Boot In Black Leather | Color: Black | Size: 8

    Madewell Shoes | Madewell Gwenda Platform Ankle Boot In Black Leather | Color: Black | Size: 8

    Worn 2 Times With Stretch Gores, A Chunky Platform And Stacked Heel, These Leather Ankle Boots Are The Best Of Both Worldscomfy And Cool. Plus, Our Mwl Cloudlift Lite Padding Makes It Feel Like You're Walking On A...Well, You Know. more

    $118.00

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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 Genuine Leather Clog Boot | Color: Black | Size: 11

    Madewell Shoes | Madewell Black Genuine Leather Clog Boot | Color: Black | Size: 11

    Gently Worn Madewell Black Leather Clog Boots With Stretch On Each Side. Measurements And Minor Imperfections Shown In Pics. Ask Me Any Questions more

    $50.00

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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 Velvet Effect Ankle Boots 7.5 | Color: Gray/Silver | Size: 7.5

    Madewell Shoes | Madewell Velvet Effect Ankle Boots 7.5 | Color: Gray/Silver | Size: 7.5

    Very Good Condition - Some Minor Wear. Ankle Boot With Black Stretch Knit. Low Heel 1.5”. Comes With Box more

    $25.00

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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 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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    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 | Euc Madewell Laura Boots Size 8.5 | Color: Brown/Tan | Size: 8.5

    Madewell Shoes | Euc Madewell Laura Boots Size 8.5 | Color: Brown/Tan | Size: 8.5

    Excellent Condition!! Madewell Laura Boots Size 8.5 Cognac Genuine Leather They Have Some Stretch In The Shaft So It Doesn’t Rub Your Ankle Like Other Booties Do!! Ankle Boots Bundle For A Discount Or Send Me An Offer! more

    $45.00

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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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    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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    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boot | Color: Black | Size: 6.5

    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boot | Color: Black | Size: 6.5

    Product Details 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... more

    $100.00

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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 The Gwenda Platform Ankle Boot Sz 6.5 Nn019 | Color: Black | Size: 6.5

    Madewell Shoes | Madewell The Gwenda Platform Ankle Boot Sz 6.5 Nn019 | Color: Black | Size: 6.5

    Preowned, Some Scuffs Here And There And When You Walk In Them, There Is A Sound Like There Is Something Loose In One Heel, There Is Just A Rattling Sound But Otherwise Great Condition With Stretch Gores, A Chunky Platform And Stacked Heel, These... more

    $95.00

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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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    Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Black | Size: 9

    Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Black | Size: 9

    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. When You Select Your Size, "H" Equals A Half... more

    $100.00

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    Madewell Shoes | Madewell Ainsley Chelsea Boot - Black Leather - 8 | Color: Black | Size: 8

    Madewell Shoes | Madewell Ainsley Chelsea Boot - Black Leather - 8 | Color: Black | Size: 8

    Madewell Ainsley Chelsea Boot - Black Leather Size 8 Great Preowned Condition Great Black Leather That Has Been Conditioned And Great Grip Soles For Great Traction. As Shown In Pictures And Video Crafted From Buttery Leather, This Updated Chelsea Boot... more

    $77.00

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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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    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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    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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    Madewell Shoes | Madewell Gloria Boot Snakeskin | Color: Black/Red | Size: 9

    Madewell Shoes | Madewell Gloria Boot Snakeskin | Color: Black/Red | Size: 9

    Excellent Condition! Super Comfy, Good Stretch To This Kind Of Leather. I Just Cannot Wear Any Type Of Heels Anymore! more

    $25.00

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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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    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 $198 The Wyckoff Chelsea Lugsole Boot Black Leather Size 12 Nn020 | Color: Black | Size: 12

    Madewell Shoes | Madewell $198 The Wyckoff Chelsea Lugsole Boot Black Leather Size 12 Nn020 | Color: Black | Size: 12

    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 Benning Chelsea Boot Warm Cinnamon Brown Size 10 | Color: Brown | Size: 10

    Madewell Shoes | Madewell Benning Chelsea Boot Warm Cinnamon Brown Size 10 | Color: Brown | Size: 10

    Some Scratching And Scuffing Throughout And Wear To The Soles. Details: 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... more

    $87.00

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    Madewell Shoes | Madewell Lonny Black Leather Ankle Boots Block Heel Pull On Stretch | Color: Black | Size: 8.5

    Madewell Shoes | Madewell Lonny Black Leather Ankle Boots Block Heel Pull On Stretch | Color: Black | Size: 8.5

    Such Great Basic Booties, Go With Everything! more

    $13.00

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    More information about Men's Shoes

    Best prices on Madewell shoes madewell suede desert, Stretchable, Boots 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.