You're in Men's Shoes

Need a Personal Shopper?

Subscribe to
Bizrate emails for the hottest
deals & products
,
PLUS a chance to

WIN $25

sign me up!

New winners chosen weekly.
No purchase necessary.

Best Seller
Madewell Shoes | New Madewell The Ivy Chelsea Dark Coffee Croco Embossed Leather Boots Size 5 | Color: Black/Brown | Size: 5

Madewell Shoes | New Madewell The Ivy Chelsea Dark Coffee Croco Embossed Leather Boots Size 5 | Color: Black/Brown | Size: 5

Details: We Toughened Up Classic Chelsea Boots With A Utilitarian Lug Sole. Made Of Crocodile Embossed Leather, They'll Look Cooler And Cooler The More You Wear 'Em. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well,... ... more

Madewell Shoes | New Madewell The Ivy Chelsea Dark Coffee Croco Embossed Leather Boots Size 5 | Color: Black/Brown | Size: 5

Details: We Toughened Up Classic Chelsea Boots With A Utilitarian Lug Sole. Made Of Crocodile Embossed Leather, They'll Look Cooler And Cooler The More You Wear 'Em. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well,...

Poshmark

$120.00

go to store
Madewell Shoes | Madewell Ivy Chelsea Boot In Leather | Color: Black | Size: 6.5

Madewell Shoes | Madewell Ivy Chelsea Boot In Leather | Color: Black | Size: 6.5

“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 Padding Feels Like Walking On A...Well, You Know. 5 1/4" Shaft... ... more

Madewell Shoes | Madewell Ivy Chelsea Boot In Leather | Color: Black | Size: 6.5

“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 Padding Feels Like Walking On A...Well, You Know. 5 1/4" Shaft...

Poshmark

$145.00

go to store
Best Seller
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

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!

Poshmark

$70.00

go to store
Madewell Shoes | Madewell ‘The Ivy’ Chelsea Boot In Leather | Color: Black/Tan | Size: 8.5

Madewell Shoes | MadewellThe IvyChelsea Boot In Leather | Color: Black/Tan | Size: 8.5

MadewellThe IvyChelsea Boot In Leather. Madewell Toughened Up These 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: The Mwl Cloudlift Lite Padding... ... more

Madewell Shoes | Madewell ‘The Ivy’ Chelsea Boot In Leather | Color: Black/Tan | Size: 8.5

Madewell ‘The Ivy’ Chelsea Boot In Leather. Madewell Toughened Up These 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: The Mwl Cloudlift Lite Padding...

Poshmark

$129.00

go to store
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

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...

Poshmark

$125.00

go to store
Madewell Shoes | Madewell Ivy Chelsea Boot In Leather | Color: Black | Size: 7

Madewell Shoes | Madewell Ivy Chelsea Boot In Leather | Color: Black | Size: 7

Only Worn A Handful Of Times. Super Cute But A Bit Too Narrow For Me. Size 7.5. Slightly Misshapen Due To Storage In A Box, But Otherwise In Great Condition. See Description From Madewell Below: We Toughened Up Classic Chelsea Boots With A Utilitarian... ... more

Madewell Shoes | Madewell Ivy Chelsea Boot In Leather | Color: Black | Size: 7

Only Worn A Handful Of Times. Super Cute But A Bit Too Narrow For Me. Size 7.5. Slightly Misshapen Due To Storage In A Box, But Otherwise In Great Condition. See Description From Madewell Below: We Toughened Up Classic Chelsea Boots With A Utilitarian...

Poshmark

$55.00

go to store
Madewell Shoes | Madewell The Ivy Chelsea Boot In Leather Sz 5/5.5 #Ma426 | Color: Black | Size: 5/5.5

Madewell Shoes | Madewell The Ivy Chelsea Boot In Leather Sz 5/5.5 #Ma426 | Color: Black | Size: 5/5.5

Sellers Note: Boots Are Size 5 .5 (9.5” Toe To Heel)On The Left Foot And Size 5 (9.25” Toe To Heel) On The Right Foot. Difference Of 0.25” We Toughened Up Classic Chelsea Boots With A Utilitarian Lug Sole. Made Of Rich Leather, They'll Look Cooler And... ... more

Madewell Shoes | Madewell The Ivy Chelsea Boot In Leather Sz 5/5.5 #Ma426 | Color: Black | Size: 5/5.5

Sellers Note: Boots Are Size 5 .5 (9.5” Toe To Heel)On The Left Foot And Size 5 (9.25” Toe To Heel) On The Right Foot. Difference Of 0.25” We Toughened Up Classic Chelsea Boots With A Utilitarian Lug Sole. Made Of Rich Leather, They'll Look Cooler And...

Poshmark

$99.00

go to store
Madewell Shoes | Madewell Ivy Chelsea Leather Boots Ma426 Size 6 | Color: Black | Size: 6

Madewell Shoes | Madewell Ivy Chelsea Leather Boots Ma426 Size 6 | Color: Black | Size: 6

Good Used Condition- Creases/Wrinkles, Few Flaws On Front Of Left Boot, Some Marks On Uppers, And A Couple Spots On Midsoles. Size 6. Style Ma426. Black And Tan. Back Heel Pull Tabs. Pull On. Preppy. Fall. Trending. Approximate Measurements: 3/4" Heel.... ... more

Madewell Shoes | Madewell Ivy Chelsea Leather Boots Ma426 Size 6 | Color: Black | Size: 6

Good Used Condition- Creases/Wrinkles, Few Flaws On Front Of Left Boot, Some Marks On Uppers, And A Couple Spots On Midsoles. Size 6. Style Ma426. Black And Tan. Back Heel Pull Tabs. Pull On. Preppy. Fall. Trending. Approximate Measurements: 3/4" Heel....

Poshmark

$85.00

go to store
Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

Reposhing This Item I Purchased From @Cooldudz. Used 1x For A Wedding Rehearsal And Now That I Am Working From Home I Don’t Wear/Need Heels Anymore. Loved Them, Fit Well And Very Stylish. ... more

Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

Reposhing This Item I Purchased From @Cooldudz. Used 1x For A Wedding Rehearsal And Now That I Am Working From Home I Don’t Wear/Need Heels Anymore. Loved Them, Fit Well And Very Stylish.

Poshmark

$50.00

go to store
Madewell Shoes | Madewell The Ivy Chelsea Boot In Croc Embossed Leather | Color: Brown/Tan | Size: 7

Madewell Shoes | Madewell The Ivy Chelsea Boot In Croc Embossed Leather | Color: Brown/Tan | Size: 7

New Without Box Woman’s Madewell Croc Style Leather Ankle Boots. The Ivy Chelsea Boot In Croc Embossed Leather. Hard To Find Print. Size 7. These Are $210 New! Check Out My Other Listings To Bundle And Save. Reasonable Offers Accepted. Items Are Cross... ... more

Madewell Shoes | Madewell The Ivy Chelsea Boot In Croc Embossed Leather | Color: Brown/Tan | Size: 7

New Without Box Woman’s Madewell Croc Style Leather Ankle Boots. The Ivy Chelsea Boot In Croc Embossed Leather. Hard To Find Print. Size 7. These Are $210 New! Check Out My Other Listings To Bundle And Save. Reasonable Offers Accepted. Items Are Cross...

Poshmark

$60.00

go to store
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

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

Poshmark

$118.00

go to store
Madewell Shoes | Madewell The Ivy Chelsea Boot In Croc Embossed Leather In Brown. | Color: Brown | Size: 6.5

Madewell Shoes | Madewell The Ivy Chelsea Boot In Croc Embossed Leather In Brown. | Color: Brown | Size: 6.5

Madewell The Ivy Chelsea Boot In Croc Embossed Leather In Brown, Size 6.5 Great Condition, Normal Signs Of Use, See The Pictures. Sole: 10" ... more

Madewell Shoes | Madewell The Ivy Chelsea Boot In Croc Embossed Leather In Brown. | Color: Brown | Size: 6.5

Madewell The Ivy Chelsea Boot In Croc Embossed Leather In Brown, Size 6.5 Great Condition, Normal Signs Of Use, See The Pictures. Sole: 10"

Poshmark

$81.00

go to store
Madewell Shoes | Madewell The Ivy Animal Print Calf Hair Leather Chelsea Boots | Color: Brown/Tan | Size: 9.5

Madewell Shoes | Madewell The Ivy Animal Print Calf Hair Leather Chelsea Boots | Color: Brown/Tan | Size: 9.5

Brand New Madewell Calf Hair Chelsea Ankle Boots. Technically These Are Size 10 But They Run Bit Small. I Would Say They Would Be Perfect For Size 9.5. ... more

Madewell Shoes | Madewell The Ivy Animal Print Calf Hair Leather Chelsea Boots | Color: Brown/Tan | Size: 9.5

Brand New Madewell Calf Hair Chelsea Ankle Boots. Technically These Are Size 10 But They Run Bit Small. I Would Say They Would Be Perfect For Size 9.5.

Poshmark

$45.00

go to store
Madewell Shoes | Madewell The Citywalk Lugsole Chelsea Boot In Calf Hair Size 6.5 Like New | Color: Black/Tan | Size: 6.5

Madewell Shoes | Madewell The Citywalk Lugsole Chelsea Boot In Calf Hair Size 6.5 Like New | Color: Black/Tan | Size: 6.5

Like New No Box Easy Pull In Style Small Imperfection In Elastic (See Picture) Size 6.5 ... more

Madewell Shoes | Madewell The Citywalk Lugsole Chelsea Boot In Calf Hair Size 6.5 Like New | Color: Black/Tan | Size: 6.5

Like New No Box Easy Pull In Style Small Imperfection In Elastic (See Picture) Size 6.5

Poshmark

$100.00

go to store
Madewell Shoes | Madewell Ivy Chelsea Boot | Size 6.5 | Color: Black | Size: 6.5

Madewell Shoes | Madewell Ivy Chelsea Boot | Size 6.5 | Color: Black | Size: 6.5

Madewell Ivy Chelsea Boot In Black Leather, Size 6.5 Women’s ... more

Madewell Shoes | Madewell Ivy Chelsea Boot | Size 6.5 | Color: Black | Size: 6.5

Madewell Ivy Chelsea Boot In Black Leather, Size 6.5 Women’s

Poshmark

$100.00

go to store
Madewell Shoes | Madewell Ivy Chelsea Boots Sz 9.5 | Color: Black | Size: 9.5

Madewell Shoes | Madewell Ivy Chelsea Boots Sz 9.5 | Color: Black | Size: 9.5

Brand New With Box Size 9.5. In Black Leather. ... more

$179.00

go to store
Madewell Shoes | Madewell The Ivy Chelsea Boot In Mini Dot Calf Hair Size 7 | Color: Black/Tan | Size: 7

Madewell Shoes | Madewell The Ivy Chelsea Boot In Mini Dot Calf Hair Size 7 | Color: Black/Tan | Size: 7

We Toughened Up Classic Chelsea Boots With A Utilitarian Lug Sole. Made Of Spotted Calf Hair, They'll Look Cooler And Cooler The More You Wear 'Em. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. 5 1/4"... ... more

Madewell Shoes | Madewell The Ivy Chelsea Boot In Mini Dot Calf Hair Size 7 | Color: Black/Tan | Size: 7

We Toughened Up Classic Chelsea Boots With A Utilitarian Lug Sole. Made Of Spotted Calf Hair, They'll Look Cooler And Cooler The More You Wear 'Em. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. 5 1/4"...

Poshmark

$105.00

go to store
Madewell Shoes | Last Pair- Madewell Ivy Calf Hair Chelsea Boot Size 7 | Color: Black/Tan | Size: 7

Madewell Shoes | Last Pair- Madewell Ivy Calf Hair Chelsea Boot Size 7 | Color: Black/Tan | Size: 7

New Never Worn Last Available Pair Size 7 Madewell Ultra-Trendy Ivy Chelsea Boot That's Designed In A Luxe Genuine Calf Hair Silhouette. 5.5" Shaft Height Slip-On Cushioned Insole Round Toe Gored Side Paneling Back Pull-Tab Genuine Dyed Calf Hair... ... more

Madewell Shoes | Last Pair- Madewell Ivy Calf Hair Chelsea Boot Size 7 | Color: Black/Tan | Size: 7

New Never Worn Last Available Pair Size 7 Madewell Ultra-Trendy Ivy Chelsea Boot That's Designed In A Luxe Genuine Calf Hair Silhouette. 5.5" Shaft Height Slip-On Cushioned Insole Round Toe Gored Side Paneling Back Pull-Tab Genuine Dyed Calf Hair...

Poshmark

$53.00

go to store
Madewell Shoes | Madewell Ivy Genuine Calf Hair Chelsea Boot Euc Sz 7.5 | Color: Black/Tan | Size: 7.5

Madewell Shoes | Madewell Ivy Genuine Calf Hair Chelsea Boot Euc Sz 7.5 | Color: Black/Tan | Size: 7.5

Madewell Ivy Genuine Calf Hair Chelsea Boot Euc Sz 7.5 In Excellent Condition, Worn Maybe Once Or Twice. Minimal Signs Of Use. Review All Pics ... more

Madewell Shoes | Madewell Ivy Genuine Calf Hair Chelsea Boot Euc Sz 7.5 | Color: Black/Tan | Size: 7.5

Madewell Ivy Genuine Calf Hair Chelsea Boot Euc Sz 7.5 In Excellent Condition, Worn Maybe Once Or Twice. Minimal Signs Of Use. Review All Pics

Poshmark

$111.00

go to store
Madewell Shoes | Madewell The Ivy Chelsea Boot Mini Dot Ankle Boots Calf Hair Size 7 | Color: Brown | Size: 7

Madewell Shoes | Madewell The Ivy Chelsea Boot Mini Dot Ankle Boots Calf Hair Size 7 | Color: Brown | Size: 7

Madewell Ivy Chelsea Mini Dot Animal Print Ankle Boots Calf Hair Size 7 Like New ... more

Madewell Shoes | Madewell The Ivy Chelsea Boot Mini Dot Ankle Boots Calf Hair Size 7 | Color: Brown | Size: 7

Madewell Ivy Chelsea Mini Dot Animal Print Ankle Boots Calf Hair Size 7 Like New

Poshmark

$160.00

go to store
Madewell Shoes | Madewell The Carina Chelsea Boot In True Black Leather | Color: Black | Size: 7.5

Madewell Shoes | Madewell The Carina Chelsea Boot In True Black Leather | Color: Black | Size: 7.5

With An Easy Rounded Toe And Comfy Stacked Mid-Height Heel, These Wear-Everywhere Leather Chelsea Boots Have Elastic Goring And A Pull-Tab That Makes On-And-Off A Breeze. Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well,... ... more

Madewell Shoes | Madewell The Carina Chelsea Boot In True Black Leather | Color: Black | Size: 7.5

With An Easy Rounded Toe And Comfy Stacked Mid-Height Heel, These Wear-Everywhere Leather Chelsea Boots Have Elastic Goring And A Pull-Tab That Makes On-And-Off A Breeze. Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well,...

Poshmark

$65.00

go to store
Madewell Shoes | Madewell Chelsea Boots, Size 6, Black, Leather | Color: Black | Size: 6

Madewell Shoes | Madewell Chelsea Boots, Size 6, Black, Leather | Color: Black | Size: 6

Madewell Chelsea Boots, Size 6, Leather, Black. Only Worn A Couple Of Times, Like New, Good Condition. ... more

Madewell Shoes | Madewell Chelsea Boots, Size 6, Black, Leather | Color: Black | Size: 6

Madewell Chelsea Boots, Size 6, Leather, Black. Only Worn A Couple Of Times, Like New, Good Condition.

Poshmark

$40.00

go to store
Madewell Shoes | Madewell The Bradley Chelsea Lugsole Boot Black Leather | Color: Black | Size: 8.5

Madewell Shoes | Madewell The Bradley Chelsea Lugsole Boot Black Leather | Color: Black | Size: 8.5

Reposhing This Item I Purchased From @Awkwardgirl2. Loved It, But Ready To Rotate For Something New. Like New Condition, Only Worn A Few Times. Super Comfortable! Questions? Leave A Comment Below! ... more

Madewell Shoes | Madewell The Bradley Chelsea Lugsole Boot Black Leather | Color: Black | Size: 8.5

Reposhing This Item I Purchased From @Awkwardgirl2. Loved It, But Ready To Rotate For Something New. Like New Condition, Only Worn A Few Times. Super Comfortable! Questions? Leave A Comment Below!

Poshmark

$98.00

go to store
Madewell Shoes | Madewell Black Leather Boots | Like New | Size 7 | Color: Black | Size: 7

Madewell Shoes | Madewell Black Leather Boots | Like New | Size 7 | Color: Black | Size: 7

Madewell Black Leather Boots | Like New | Size 7 ... more

$127.00

go to store
Madewell Shoes | Madewell Rosie Black Leather Ankle Boots In Like-New Condition. Size 9.5. | Color: Black | Size: 9.5

Madewell Shoes | Madewell Rosie Black Leather Ankle Boots In Like-New Condition. Size 9.5. | Color: Black | Size: 9.5

Madewell Rosie Black Leather Ankle Boots In Like-New Condition. Size 9.5. Stacked Heel. Side Zippers For Easy On/Off. Padded Footbed For Extra Comfort. 2.5" Heel. There Is No Wear On The Boots, Not Even On The Soles. Sold Out On Website. ... more

Madewell Shoes | Madewell Rosie Black Leather Ankle Boots In Like-New Condition. Size 9.5. | Color: Black | Size: 9.5

Madewell Rosie Black Leather Ankle Boots In Like-New Condition. Size 9.5. Stacked Heel. Side Zippers For Easy On/Off. Padded Footbed For Extra Comfort. 2.5" Heel. There Is No Wear On The Boots, Not Even On The Soles. Sold Out On Website.

Poshmark

$80.00

go to store
Madewell Shoes | Ivy Lugsole Chelsea Leather Boots Black Size 7.5 | Color: Black | Size: 7.5

Madewell Shoes | Ivy Lugsole Chelsea Leather Boots Black Size 7.5 | Color: Black | Size: 7.5

Ivy Lugsole Chelsea Leather Boots Black Size 7.5 Used In Good Condition. The Leather Is Soft And Supple From Wear With Some Wrinkles But These Shoes Have A Ton Of Life Left In Them And No Significant Cosmetic Issues. They’re Just Too Narrow For My... ... more

Madewell Shoes | Ivy Lugsole Chelsea Leather Boots Black Size 7.5 | Color: Black | Size: 7.5

Ivy Lugsole Chelsea Leather Boots Black Size 7.5 Used In Good Condition. The Leather Is Soft And Supple From Wear With Some Wrinkles But These Shoes Have A Ton Of Life Left In Them And No Significant Cosmetic Issues. They’re Just Too Narrow For My...

Poshmark

$40.00

go to store
Madewell Shoes | Madewell Chelsea Black Leather Boots #F5092 Bootie | Color: Black | Size: 7.5

Madewell Shoes | Madewell Chelsea Black Leather Boots #F5092 Bootie | Color: Black | Size: 7.5

Reposhing This Item I Purchased From @Sally_emm1987. Loved It, But I Now Wear Barefoot Shoes So Selling My Shoes! ... more

Madewell Shoes | Madewell Chelsea Black Leather Boots #F5092 Bootie | Color: Black | Size: 7.5

Reposhing This Item I Purchased From @Sally_emm1987. Loved It, But I Now Wear Barefoot Shoes So Selling My Shoes!

Poshmark

$70.00

go to store
Madewell Shoes | Madewell The Ainsley Chelsea Leather Boot In Black Size 7 Ankle Bootie | Color: Black | Size: 7

Madewell Shoes | Madewell The Ainsley Chelsea Leather Boot In Black Size 7 Ankle Bootie | Color: Black | Size: 7

Madewell The Ainsley Chelsea Leather Boot In Black Size 7 Ankle Booties Have Light Scuffs And Distressing But They’re High Quality/Beautifully Made And Have A Lot Of Life Left. ... more

Madewell Shoes | Madewell The Ainsley Chelsea Leather Boot In Black Size 7 Ankle Bootie | Color: Black | Size: 7

Madewell The Ainsley Chelsea Leather Boot In Black Size 7 Ankle Booties Have Light Scuffs And Distressing But They’re High Quality/Beautifully Made And Have A Lot Of Life Left.

Poshmark

$38.00

go to store
Madewell Shoes | Madewell Sz 7 The Regan Chelsea Ankle Boots Black Leather Stacked Block Heel | Color: Black | Size: 7

Madewell Shoes | Madewell Sz 7 The Regan Chelsea Ankle Boots Black Leather Stacked Block Heel | Color: Black | Size: 7

Step Up Your Shoe Game With These Stylish Chelsea Ankle Boots By Madewell. Crafted With Black Leather, These Boots Feature A Round Toe Shape And A Pull-On Closure For Easy Wear. The Mid-Height Stacked Block Heel Provides Comfort And Style, Making Them... ... more

Madewell Shoes | Madewell Sz 7 The Regan Chelsea Ankle Boots Black Leather Stacked Block Heel | Color: Black | Size: 7

Step Up Your Shoe Game With These Stylish Chelsea Ankle Boots By Madewell. Crafted With Black Leather, These Boots Feature A Round Toe Shape And A Pull-On Closure For Easy Wear. The Mid-Height Stacked Block Heel Provides Comfort And Style, Making Them...

Poshmark

$76.00

go to store
Madewell Shoes | Madewell The Chelsea Benning Boot Sleek Black Leather Women's Size 9, Brazil | Color: Black | Size: 9

Madewell Shoes | Madewell The Chelsea Benning Boot Sleek Black Leather Women's Size 9, Brazil | Color: Black | Size: 9

These Boots Are Structurally Sound And In Good Pre-Owned Condition With Some Wear Present Including Discoloration And Scuffing Particularly Near The Toes. ... more

Madewell Shoes | Madewell The Chelsea Benning Boot Sleek Black Leather Women's Size 9, Brazil | Color: Black | Size: 9

These Boots Are Structurally Sound And In Good Pre-Owned Condition With Some Wear Present Including Discoloration And Scuffing Particularly Near The Toes.

Poshmark

$85.00

go to store
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

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...

Poshmark

$77.00

go to store
Madewell Shoes | Madewell Lonny Leather Black Heeled Chelsea Ankle Boots Size 9 | Color: Black | Size: 9

Madewell Shoes | Madewell Lonny Leather Black Heeled Chelsea Ankle Boots Size 9 | Color: Black | Size: 9

Details Round-Toe Madewell Booties Have Easy Pull-On Style With Exposed Elastic Gores Detailing The Short Shaft. Stacked Heel And Rubber Sole. Leather: Calfskin. Measurements Heel: 3.5in ... more

Madewell Shoes | Madewell Lonny Leather Black Heeled Chelsea Ankle Boots Size 9 | Color: Black | Size: 9

Details Round-Toe Madewell Booties Have Easy Pull-On Style With Exposed Elastic Gores Detailing The Short Shaft. Stacked Heel And Rubber Sole. Leather: Calfskin. Measurements Heel: 3.5in

Poshmark

$49.00

go to store
Madewell Shoes | - Madewell Black Leather Chelsea Boots | Color: Black | Size: 7.5

Madewell Shoes | - Madewell Black Leather Chelsea Boots | Color: Black | Size: 7.5

Size 7.5, Worn Just Once ... more

$56.00

go to store
Madewell Shoes | Madewell Black Leather Chelsea Boots | Color: Black | Size: 8.5

Madewell Shoes | Madewell Black Leather Chelsea Boots | Color: Black | Size: 8.5

These Boots Are In Excellent Condition. Super Comfortable And Easily Slip On And Off. I Am Only Selling Because They Fit A Too Big On Me Than I Expected. (I Sized Up On Purpose Thinking I’d Need More Room With Thick Socks And The Way My Feet Are, But... ... more

Madewell Shoes | Madewell Black Leather Chelsea Boots | Color: Black | Size: 8.5

These Boots Are In Excellent Condition. Super Comfortable And Easily Slip On And Off. I Am Only Selling Because They Fit A Too Big On Me Than I Expected. (I Sized Up On Purpose Thinking I’d Need More Room With Thick Socks And The Way My Feet Are, But...

Poshmark

$120.00

go to store
Madewell Shoes | Madewell Black Leather Chelsea Boots, Size 7 | Color: Black/Brown | Size: 7

Madewell Shoes | Madewell Black Leather Chelsea Boots, Size 7 | Color: Black/Brown | Size: 7

These Madewell Boots Have Lasted Me A Very Long Time! They’re Incredibly Comfortable And Have A Lot Of Wear Left! They Are Us Size 7 And No Longer Fit Me (I’m 7.5) So I’m Selling Them To Someone Who Can Enjoy Them! The Leather Is In Great Condition!... ... more

Madewell Shoes | Madewell Black Leather Chelsea Boots, Size 7 | Color: Black/Brown | Size: 7

These Madewell Boots Have Lasted Me A Very Long Time! They’re Incredibly Comfortable And Have A Lot Of Wear Left! They Are Us Size 7 And No Longer Fit Me (I’m 7.5) So I’m Selling Them To Someone Who Can Enjoy Them! The Leather Is In Great Condition!...

Poshmark

$80.00

go to store
Madewell Shoes | Madewell Lonny Ankle Boots Booties Black Leather Chelsea 9.5 | Color: Black | Size: 9.5

Madewell Shoes | Madewell Lonny Ankle Boots Booties Black Leather Chelsea 9.5 | Color: Black | Size: 9.5

Madewell Lonny Ankle Boots Booties Black Leather Chelsea. Heeled 3.5” Stacked Wood Chunky Heels. Elastic Goring On The Sides With A Decorative Strap. ... more

Madewell Shoes | Madewell Lonny Ankle Boots Booties Black Leather Chelsea 9.5 | Color: Black | Size: 9.5

Madewell Lonny Ankle Boots Booties Black Leather Chelsea. Heeled 3.5” Stacked Wood Chunky Heels. Elastic Goring On The Sides With A Decorative Strap.

Poshmark

$60.00

go to store
Madewell Shoes | Madewell The Benning Chelsea Boot In True Black Leather | Color: Black | Size: 8

Madewell Shoes | Madewell The Benning Chelsea Boot In True Black Leather | Color: Black | Size: 8

Madewell The Benning Chelsea Boot In True Black Leather Size 8 In Good Condition Features: Stylish, Leather, Neutral, Madewell, Winter, Fall, Fall Fashion, Trendy, Booties, Boots, Staple, Timeless, Everyday, Everyday Style, Chelsea Boot Size: Womens 8 ... more

Madewell Shoes | Madewell The Benning Chelsea Boot In True Black Leather | Color: Black | Size: 8

Madewell The Benning Chelsea Boot In True Black Leather Size 8 In Good Condition Features: Stylish, Leather, Neutral, Madewell, Winter, Fall, Fall Fashion, Trendy, Booties, Boots, Staple, Timeless, Everyday, Everyday Style, Chelsea Boot Size: Womens 8

Poshmark

$90.00

go to store
Madewell Shoes | Madewell Sonia Chelsea Black Leather Boots Truck Ankle Block Heel M3461 Size 7.5 | Color: Black | Size: 7.5

Madewell Shoes | Madewell Sonia Chelsea Black Leather Boots Truck Ankle Block Heel M3461 Size 7.5 | Color: Black | Size: 7.5

Madewell ... more

$63.00

go to store
Madewell Shoes | Madewell Citywalk Lugsole Chelsea Boot In Black Leather Sz | Color: Black | Size: 6.5

Madewell Shoes | Madewell Citywalk Lugsole Chelsea Boot In Black Leather Sz | Color: Black | Size: 6.5

Worn 2-3 Times. They Were Just Too Small On Me. They Are True To Size! Perfect Chelsea Boots (I Ended Up Getting A Bigger Pair That’s How Much I Love Them!). Leather Upper, Size 6.5, Lug Sole Bottom, Cloudlift Lite Padding For Super Comfy Wear. ... more

Madewell Shoes | Madewell Citywalk Lugsole Chelsea Boot In Black Leather Sz | Color: Black | Size: 6.5

Worn 2-3 Times. They Were Just Too Small On Me. They Are True To Size! Perfect Chelsea Boots (I Ended Up Getting A Bigger Pair That’s How Much I Love Them!). Leather Upper, Size 6.5, Lug Sole Bottom, Cloudlift Lite Padding For Super Comfy Wear.

Poshmark

$95.00

go to store