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    Best Seller
    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 Suede Leather Western Ankle Boots Size 8 Carmel Brown | Color: Brown | Size: 8

    Madewell Shoes | Madewell Suede Leather Western Ankle Boots Size 8 Carmel Brown | Color: Brown | Size: 8

    Madewell Suede Leather Western Cowgirl Ankle Boots Size 8 Carmel Brown Stretchy Opening Light Wear To Suede Toe Area And Soles Pre Owned Good Condition more

    $46.00

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    Best Seller
    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 | 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 Short Chelsea Boot Black Leather Size 7 | Color: Black | Size: 7

    Madewell Shoes | Madewell Short Chelsea Boot Black Leather Size 7 | Color: Black | Size: 7

    Pre-Owned Madewell Short Chelsea Boot, Leather, Black Size 7. Great Used Condition With Minimal Signs Of Wear, Dirty On The Bottom Soles, No Visible Issues. Pull On, Stacked Heel, Leather Upper And Interior, And Accordion Style For Some Stretch Around... more

    $85.00

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    Madewell Shoes | New Madewell Size 10 Wyckoff Chelsea Lugsole Boots In Smoked Graphite Suede | Color: Gray | Size: 10

    Madewell Shoes | New Madewell Size 10 Wyckoff Chelsea Lugsole Boots In Smoked Graphite Suede | Color: Gray | Size: 10

    New Without Box. Store Display Models And May Have Minor Try On/Shelf Wear - See Pics. Line On Inside Label To Prevent In Store Returns. Size 10 Color: Smoked Graphite Suede Ready For All Your Supercute Fall Fits, These Suede Chelsea Boots Have... more

    $119.00

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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 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 The Benning Chelsea Boot Sz 6 Nn017 | Color: Black | Size: 6

    Madewell Shoes | Madewell The Benning Chelsea Boot Sz 6 Nn017 | Color: Black | Size: 6

    Boots Are New Without Box, Display Item, So The Bottoms Are A Tad Dirty 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

    $80.00

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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 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 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 The Benning Chelsea Boot | Color: Gold/Tan | Size: 6.5

    Madewell Shoes | Madewell The Benning Chelsea Boot | Color: Gold/Tan | Size: 6.5

    Preowned In Great Condition! Madewell 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. When You Select Your... more

    $82.00

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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

    $57.00

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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 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 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 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 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 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 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 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 | 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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    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 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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    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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    More information about Men's Shoes

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