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    Best Seller
    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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    Best Seller
    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 | 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

    $70.00

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    Madewell Shoes | Madewell “The Western Ankle Boot In Suede” -Walnut Shell Size 7 | Color: Brown/Cream | Size: 7

    Madewell Shoes | Madewell “The Western Ankle Boot In Suede” -Walnut Shell Size 7 | Color: Brown/Cream | Size: 7

    Pre-Loved Condition Comes With Box Modern And Chic, The Madewell The Western Ankle Boot In Suede Are A Must-Have In Your Footwear Collection. Crafted From Smooth Leather Upper. Breathable Leather And Textile Lining And Insole. Stretch Pull-On Style.... more

    $40.00

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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 Lonny Boots | Color: Brown | Size: 7

    Madewell Shoes | Madewell Lonny Boots | Color: Brown | Size: 7

    Cute Ankle Height Madewell Booties. Stacked Heel For Added Height. Brown On Brown Stretch Panel With Ankle Strap Detail. Used Condition With Some Scuffs And Scrapes But Still Very Cute And Good Looking. more

    $22.00

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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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    Madewell Shoes | Madewell Ankle Boot, Suede, | Color: Cream | Size: 8.5

    Madewell Shoes | Madewell Ankle Boot, Suede, | Color: Cream | Size: 8.5

    Madewell The Western Ankle Boot In Suede Walnut Shell I Wore These Darling Ankle Boots Maybe 4 Times. I Love Them And They Are Very Comfortable! They Go With Everything! The 2 1/4" Heel Looks Cute With Dresses As Well. The Pull Tab And Covered Elastic... more

    $74.00

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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

    $70.00

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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 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 $198 The Wyckoff Chelsea Lugsole Boot Leather Size 10.5 Nn020 | Color: Black/Cream | Size: 10.5

    Madewell Shoes | Madewell $198 The Wyckoff Chelsea Lugsole Boot Leather Size 10.5 Nn020 | Color: Black/Cream | Size: 10.5

    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.6" Shaft Height1 1/2"... more

    $70.00

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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 6.5 Ainsley Brown Leather Chelsea Boots | Color: Brown | Size: 6.5

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

    Madewell 6.5 Ainsley Brown Leather Chelsea Boots. Used, Good Conditionsee Pictures, Plenty Of Life Left. Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: Our Mwl... more

    $28.00

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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 Size 6 The Benning Chelsea Boot In Warm Cinnamon | Color: Brown/Tan | Size: 6

    Madewell Shoes | Madewell Size 6 The Benning Chelsea Boot In Warm Cinnamon | Color: Brown/Tan | Size: 6

    New With Defects. Store Display Models And Have A Couple Areas Of Discoloration In The Leather - See Pics. Line On Inside Label To Prevent In Store Returns. Size 6 Color: Warm Cinnamon Coming In Supersoft Leather, These Chelsea Boot Have Stretchy Gores... more

    $74.00

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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 $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

    $97.00

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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 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 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 Ainsley Chelsea Boot | Color: Brown/Tan | Size: 8

    Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Brown/Tan | Size: 8

    Madewell The Ainsley Chelsea Boot Size 8. English Saddle Never Worn And Comes With Original Box. Crafted From Buttery Leather And The Mwl Cloudlift Lite Padding For Extra Comfort. Please Note: These Boots Fit Narrow But Will Stretch With Wear From... more

    $80.00

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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 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 | New Madewell The Benning Chelsea Boot In Warm Cinnamon | Color: Brown/Tan | Size: Various

    Madewell Shoes | New Madewell The Benning Chelsea Boot In Warm Cinnamon | Color: Brown/Tan | Size: Various

    New Without Box. Line On Inside Label To Prevent In Store Returns. Color: Warm Cinnamon 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... more

    $118.00

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    Madewell Shoes | Madewell Suede The Bea Boot Size 7 Embroidered Ankle Zip Boho Metallic Booties | Color: Orange | Size: 7

    Madewell Shoes | Madewell Suede The Bea Boot Size 7 Embroidered Ankle Zip Boho Metallic Booties | Color: Orange | Size: 7

    Madewell Suede The Bea Boot Size 7 Embroidered Ankle Zip Boho Size: 7 In Great Pre-Owned Condition With Some Signs Of Wear On The Heel As Shown In Photos. Check Photos Pls. Check Out My Profile For More Deals! #900 Tags; Vintage, Y2k, 2000s, Corduroy,... more

    $27.00

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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 Boot Sz 10 Nn020 | Color: Black | Size: 10

    Madewell Shoes | Madewell The Wyckoff Chelsea Lugsole Boot Sz 10 Nn020 | Color: Black | Size: 10

    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

    $89.00

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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 The Nico Boot | Color: Black | Size: 9

    Madewell Shoes | Madewell The Nico Boot | Color: Black | Size: 9

    Nico Ankle Boot. Black Leather With Pointed Toe, Stretch Elastic Gusset, Pull Tabs On Back. Few Scuffs And Wear At Toe Tips. more

    $55.00

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

    Madewell Shoes | Madewell The Ainsley Chelsea Boot J8295 | Color: Brown | 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. - Please Note: These Boots Fit Narrow But... more

    $89.00

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    More information about Men's Shoes

    Best prices on Madewell shoes madewell rowan gladiator, 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.