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 | 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

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

Poshmark

$50.00

go to store
Madewell Shoes | Madewell Ainsley Chelsea Leather Shearling Slip On Ankle Boot Brown | Size 10 | Color: Brown/Tan | Size: 10

Madewell Shoes | Madewell Ainsley Chelsea Leather Shearling Slip On Ankle Boot Brown | Size 10 | Color: Brown/Tan | Size: 10

Madewell Ainsley Chelsea Leather Shearling Slip On Ankle Boot In Brown | Size 10 In Excellent Preowned Condition. Upper Leather Is In Great Condition With A Few Minor Marks, Wear Is To Tread Of Shoe. Please See All The Pictures. Color: Brown Tan Cognac... ... more

Madewell Shoes | Madewell Ainsley Chelsea Leather Shearling Slip On Ankle Boot Brown | Size 10 | Color: Brown/Tan | Size: 10

Madewell Ainsley Chelsea Leather Shearling Slip On Ankle Boot In Brown | Size 10 In Excellent Preowned Condition. Upper Leather Is In Great Condition With A Few Minor Marks, Wear Is To Tread Of Shoe. Please See All The Pictures. Color: Brown Tan Cognac...

Poshmark

$40.00

go to store
Best Seller
Madewell Shoes | Madewell Nadine Ankle Chelsea Boots Spotted Calf Skin Sz 7.5 | Color: Black/Brown | Size: 7.5

Madewell Shoes | Madewell Nadine Ankle Chelsea Boots Spotted Calf Skin Sz 7.5 | Color: Black/Brown | Size: 7.5

Used Pair Of Madewell Nadine Ankle Chelsea Boots In Size 7.5. These Are A Spotted Calf Hair Upper. There Is A Little Wear On The Points Of The Toes. Minimal Heel Wear. Please See Photos ... more

Madewell Shoes | Madewell Nadine Ankle Chelsea Boots Spotted Calf Skin Sz 7.5 | Color: Black/Brown | Size: 7.5

Used Pair Of Madewell Nadine Ankle Chelsea Boots In Size 7.5. These Are A Spotted Calf Hair Upper. There Is A Little Wear On The Points Of The Toes. Minimal Heel Wear. Please See Photos

Poshmark

$35.00

go to store
Madewell Shoes | Madewell The Grayson Chelsea Boot Black Leather Pointed Toe Ankle Boots Size 10 | Color: Black/Brown | Size: 10

Madewell Shoes | Madewell The Grayson Chelsea Boot Black Leather Pointed Toe Ankle Boots Size 10 | Color: Black/Brown | Size: 10

Madewell ‘The Grayson’ Chelsea Boot Black Leather Pointed Toe Ankle Booties Size: 10 Color: Black & Brown Style: J8293 Condition: Preloved Condition (Normal Signs Of Wear; Small Flaws To Leather Noted; Creasing At Toe Noted; Please See/Zoom In To All... ... more

Madewell Shoes | Madewell The Grayson Chelsea Boot Black Leather Pointed Toe Ankle Boots Size 10 | Color: Black/Brown | Size: 10

Madewell ‘The Grayson’ Chelsea Boot Black Leather Pointed Toe Ankle Booties Size: 10 Color: Black & Brown Style: J8293 Condition: Preloved Condition (Normal Signs Of Wear; Small Flaws To Leather Noted; Creasing At Toe Noted; Please See/Zoom In To All...

Poshmark

$50.00

go to store
Madewell Shoes | Madewell The Regan Pull-On Ankle Boots In Black, Size 9.5 | Color: Black/Brown | Size: 9.5

Madewell Shoes | Madewell The Regan Pull-On Ankle Boots In Black, Size 9.5 | Color: Black/Brown | Size: 9.5

Madewell The Regan Pull-On Boot In Black Leather, Excellent Condition, Barely Worn, No Defects! Fully Cleaned & Leather Conditioned, Ready To Rock. My Photos Show It All, So No Unwelcome Surprises. Even Prettier In Person And Extremely Comfortable.... ... more

Madewell Shoes | Madewell The Regan Pull-On Ankle Boots In Black, Size 9.5 | Color: Black/Brown | Size: 9.5

Madewell The Regan Pull-On Boot In Black Leather, Excellent Condition, Barely Worn, No Defects! Fully Cleaned & Leather Conditioned, Ready To Rock. My Photos Show It All, So No Unwelcome Surprises. Even Prettier In Person And Extremely Comfortable....

Poshmark

$95.00

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

$30.00

go to store
Madewell Shoes | Madewell The Regan Black Leather Ankle Boot Bootie J8307 Pull On 9.5 Almond Toe | Color: Black/Brown | Size: 9.5

Madewell Shoes | Madewell The Regan Black Leather Ankle Boot Bootie J8307 Pull On 9.5 Almond Toe | Color: Black/Brown | Size: 9.5

In Good Preowned Condition Madewell Ankle Boot. Tagged Size 9.5. Leather Upper And Lining, Synthetic Sole. Made In Brazil. With A 2.5" Heel. Signs Of Wear, Mainly On The Heels And Toes - Please See The Last Two Photos For Detail. Open To Offers. Happy... ... more

Madewell Shoes | Madewell The Regan Black Leather Ankle Boot Bootie J8307 Pull On 9.5 Almond Toe | Color: Black/Brown | Size: 9.5

In Good Preowned Condition Madewell Ankle Boot. Tagged Size 9.5. Leather Upper And Lining, Synthetic Sole. Made In Brazil. With A 2.5" Heel. Signs Of Wear, Mainly On The Heels And Toes - Please See The Last Two Photos For Detail. Open To Offers. Happy...

Poshmark

$34.00

go to store
Madewell Shoes | Madewell Billie Boot In Black Ankle Boots Size 6 | Color: Black/Brown | Size: 6

Madewell Shoes | Madewell Billie Boot In Black Ankle Boots Size 6 | Color: Black/Brown | Size: 6

Madewell Billie Boot In Black Ankle Boots Size 6 Bundle With Other Items In My Closet And Save Even More! ... more

Madewell Shoes | Madewell Billie Boot In Black Ankle Boots Size 6 | Color: Black/Brown | Size: 6

Madewell Billie Boot In Black Ankle Boots Size 6 Bundle With Other Items In My Closet And Save Even More!

Poshmark

$48.00

go to store
Madewell Shoes | Madewell Size 8 Snakeskin Ankle Boots | Color: Black/Brown | Size: 8

Madewell Shoes | Madewell Size 8 Snakeskin Ankle Boots | Color: Black/Brown | Size: 8

An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. - 1 3/4" Heel (Size 8.5) - 3" Shaft - Pull-On Style With Elastic Gore Insets - Cushioned Footbed - Leather Upper And... ... more

Madewell Shoes | Madewell Size 8 Snakeskin Ankle Boots | Color: Black/Brown | Size: 8

An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. - 1 3/4" Heel (Size 8.5) - 3" Shaft - Pull-On Style With Elastic Gore Insets - Cushioned Footbed - Leather Upper And...

Poshmark

$50.00

go to store
Madewell Shoes | Madewell Regan Snake Embossed Leather Block Heel Ankle Boot Size 6 | Color: Black/Brown | Size: 6

Madewell Shoes | Madewell Regan Snake Embossed Leather Block Heel Ankle Boot Size 6 | Color: Black/Brown | Size: 6

Madewell Regan Leather Snake Embossed Block Heel Ankle Boot Excellent Condition With No Flaws. Now In Cooland Versatiletextural Snakeskin-Patterned Leather, These Pull-On Boots Have Block Heels For A Little Extra Height (That's Still Walking-Friendly).... ... more

Madewell Shoes | Madewell Regan Snake Embossed Leather Block Heel Ankle Boot Size 6 | Color: Black/Brown | Size: 6

Madewell Regan Leather Snake Embossed Block Heel Ankle Boot Excellent Condition With No Flaws. Now In Cooland Versatiletextural Snakeskin-Patterned Leather, These Pull-On Boots Have Block Heels For A Little Extra Height (That's Still Walking-Friendly)....

Poshmark

$29.00

go to store
Madewell Shoes | Madewell | The Western Ankle Boot In Leather (Size 7) | Color: Black/Brown | Size: 7

Madewell Shoes | Madewell | The Western Ankle Boot In Leather (Size 7) | Color: Black/Brown | Size: 7

In Good Pre-Owned Condition, I've Had These For A Little Over A Year So They've Gotten Good Use In Them, But Ready To Trade Them In For Something New! Hoping They Can Go To A Good Home As They Have Many More Years Left In Them With Classic Western... ... more

Madewell Shoes | Madewell | The Western Ankle Boot In Leather (Size 7) | Color: Black/Brown | Size: 7

In Good Pre-Owned Condition, I've Had These For A Little Over A Year So They've Gotten Good Use In Them, But Ready To Trade Them In For Something New! Hoping They Can Go To A Good Home As They Have Many More Years Left In Them With Classic Western...

Poshmark

$59.00

go to store
Madewell Shoes | Madewell Brown The Zip-Up Lugsole Ankle Rain Boot Waterproof Size 6 Rubber | Color: Black/Brown | Size: 6

Madewell Shoes | Madewell Brown The Zip-Up Lugsole Ankle Rain Boot Waterproof Size 6 Rubber | Color: Black/Brown | Size: 6

Madewell The Zip-Up Lugsole Ankle Rain Boot. Size 6. Guc. Just A Little Dirty. Cool And Comfy Rain Boots? Believe It. This Zip-Up Pair Has Rugged Lug Soles And Our Mwl Cloudlift Insoles For A Supercushy Fit That Feels Like Walking On A... Well, You... ... more

Madewell Shoes | Madewell Brown The Zip-Up Lugsole Ankle Rain Boot Waterproof Size 6 Rubber | Color: Black/Brown | Size: 6

Madewell The Zip-Up Lugsole Ankle Rain Boot. Size 6. Guc. Just A Little Dirty. Cool And Comfy Rain Boots? Believe It. This Zip-Up Pair Has Rugged Lug Soles And Our Mwl Cloudlift Insoles For A Supercushy Fit That Feels Like Walking On A... Well, You...

Poshmark

$35.00

go to store
Madewell Shoes | Madewell The Rosie Ankle Calfhair Boot Size 6 | Color: Black/Brown | Size: 6

Madewell Shoes | Madewell The Rosie Ankle Calfhair Boot Size 6 | Color: Black/Brown | Size: 6

Madewell The Rosie Ankle Calfhair Bootie In Rich Brown And Black Tones Ft. A Side Zipper Ankle, Low Block Heel, Rounded Closed Toe, Leather Insole, Calfhair Animal Print Exterior Excellent New Without Tags And Box Condition Msrp 178 Size 6 Shaft... ... more

Madewell Shoes | Madewell The Rosie Ankle Calfhair Boot Size 6 | Color: Black/Brown | Size: 6

Madewell The Rosie Ankle Calfhair Bootie In Rich Brown And Black Tones Ft. A Side Zipper Ankle, Low Block Heel, Rounded Closed Toe, Leather Insole, Calfhair Animal Print Exterior Excellent New Without Tags And Box Condition Msrp 178 Size 6 Shaft...

Poshmark

$49.00

go to store
Madewell Shoes | Madewell Brown Snake Embossed Leather Low Chelsea Ankle Boot New Size 9 | Color: Black/Brown | Size: 9

Madewell Shoes | Madewell Brown Snake Embossed Leather Low Chelsea Ankle Boot New Size 9 | Color: Black/Brown | Size: 9

Questions? Leave A Comment Below! ... more

$50.00

go to store
Madewell Shoes | Madewell Rosie Snakeskin Moonshine Ankle Booties Boots Size 6 | Color: Black/Brown | Size: 6

Madewell Shoes | Madewell Rosie Snakeskin Moonshine Ankle Booties Boots Size 6 | Color: Black/Brown | Size: 6

Madewell Rosie Snakeskin Moonshine Ankle Booties Boots Size 6 Purchased From Nordstrom, Only Tried At The Store. Excellent - Like New Condition. Sticker Residue By The Outsole. No Box. ... more

Madewell Shoes | Madewell Rosie Snakeskin Moonshine Ankle Booties Boots Size 6 | Color: Black/Brown | Size: 6

Madewell Rosie Snakeskin Moonshine Ankle Booties Boots Size 6 Purchased From Nordstrom, Only Tried At The Store. Excellent - Like New Condition. Sticker Residue By The Outsole. No Box.

Poshmark

$59.00

go to store
Madewell Shoes | Euc Madewell Reid Two Tone Block Leather Buckle Boots Black Brown Size 10 | Color: Black/Brown | Size: 11

Madewell Shoes | Euc Madewell Reid Two Tone Block Leather Buckle Boots Black Brown Size 10 | Color: Black/Brown | Size: 11

Barely Worn, Excellent Condition. Leather Upper In Smooth Black And Cognac Leather. Inner Zip Closure. Double Adjustable Accent Buckles. 3.5" Stacked Heel Leather Lining. Beautiful Boots That Can Be Dressed Up Or Dressed Down. Please Feel Free To Ask... ... more

Madewell Shoes | Euc Madewell Reid Two Tone Block Leather Buckle Boots Black Brown Size 10 | Color: Black/Brown | Size: 11

Barely Worn, Excellent Condition. Leather Upper In Smooth Black And Cognac Leather. Inner Zip Closure. Double Adjustable Accent Buckles. 3.5" Stacked Heel Leather Lining. Beautiful Boots That Can Be Dressed Up Or Dressed Down. Please Feel Free To Ask...

Poshmark

$60.00

go to store
Madewell Shoes | Madewell Insulated Ankle Boots - Size 10 | Color: Tan | Size: 10

Madewell Shoes | Madewell Insulated Ankle Boots - Size 10 | Color: Tan | Size: 10

Nwot, Worn Once, In Excellent Condition, I Am Not A Reseller. All Clothing Is From My Own Collection And Is Very Well Taken Care Of. There Are No Visible Flaws. If There Are, They Will Be Mentioned And Shown In Photos Best I Can. **Please Feel Free To... ... more

Madewell Shoes | Madewell Insulated Ankle Boots - Size 10 | Color: Tan | Size: 10

Nwot, Worn Once, In Excellent Condition, I Am Not A Reseller. All Clothing Is From My Own Collection And Is Very Well Taken Care Of. There Are No Visible Flaws. If There Are, They Will Be Mentioned And Shown In Photos Best I Can. **Please Feel Free To...

Poshmark

$50.00

go to store
Madewell Shoes | Madewell 1937 Cait Ankle Bootie Boot 2 Tone Brown Leather Side Zip Size 10 | Color: Brown | Size: 10

Madewell Shoes | Madewell 1937 Cait Ankle Bootie Boot 2 Tone Brown Leather Side Zip Size 10 | Color: Brown | Size: 10

Condition Is Used. It Is In Guc With No Rips, Holes, Or Stains. Heel Measures 2". ... more

Madewell Shoes | Madewell 1937 Cait Ankle Bootie Boot 2 Tone Brown Leather Side Zip Size 10 | Color: Brown | Size: 10

Condition Is Used. It Is In Guc With No Rips, Holes, Or Stains. Heel Measures 2".

Poshmark

$40.00

go to store
Madewell Shoes | Madewell Sonia Chelsea Black Leather Boots Truck Ankle Block Heel M3461 Size 10 | Color: Black | Size: 10

Madewell Shoes | Madewell Sonia Chelsea Black Leather Boots Truck Ankle Block Heel M3461 Size 10 | Color: Black | Size: 10

Gently Used Perfect Condition Black Leather Booties From Madewell Trendy And Beautiful Looks Great With Many Outfits Retail $168. Madewell, Cardigans, Coach, J. Crew, Mules, Tote, Free People, Anthropologie And Wedges Also Avail ... more

Madewell Shoes | Madewell Sonia Chelsea Black Leather Boots Truck Ankle Block Heel M3461 Size 10 | Color: Black | Size: 10

Gently Used Perfect Condition Black Leather Booties From Madewell Trendy And Beautiful Looks Great With Many Outfits Retail $168. Madewell, Cardigans, Coach, J. Crew, Mules, Tote, Free People, Anthropologie And Wedges Also Avail

Poshmark

$63.00

go to store
Madewell Shoes | Madewell Leather Suede Ankle Boots Tan Size 10 | Color: Brown/Tan | Size: 10

Madewell Shoes | Madewell Leather Suede Ankle Boots Tan Size 10 | Color: Brown/Tan | Size: 10

New Without Tags Size 10 Womens No Flaws 3.75 Inch Heel Height Suede Leather Upper Chunky Heel ... more

Madewell Shoes | Madewell Leather Suede Ankle Boots Tan Size 10 | Color: Brown/Tan | Size: 10

New Without Tags Size 10 Womens No Flaws 3.75 Inch Heel Height Suede Leather Upper Chunky Heel

Poshmark

$65.00

go to store
Madewell Shoes | Madewell The Ainsley Chelsea Boot In Black Leather, Size 5 | Color: Black | Size: 5

Madewell Shoes | Madewell The Ainsley Chelsea Boot In Black Leather, Size 5 | Color: Black | Size: 5

Madewell The Ainsley Chelsea Boot In Black - Back Leather Pull -Slip On Style -Block Heel -Used Condition ... more

Madewell Shoes | Madewell The Ainsley Chelsea Boot In Black Leather, Size 5 | Color: Black | Size: 5

Madewell The Ainsley Chelsea Boot In Black - Back Leather Pull -Slip On Style -Block Heel -Used Condition

Poshmark

$30.00

go to store
Madewell Shoes | Madewell Regan Boot | Black Ankle Bootie | Color: Black/Brown | Size: 6.5

Madewell Shoes | Madewell Regan Boot | Black Ankle Bootie | Color: Black/Brown | Size: 6.5

Nwot, Unworn (Outside Of House); In Excellent Condition!* Cool Rich Leather Pull-On Boots With Block Heels For A Little Extra Height. Made With Mwl Cloudlift Lite Padding For Extra Comfort! Size: 6.5; Fits Tts 4 1/2" Shaft Height (Based On Size 7) 2... ... more

Madewell Shoes | Madewell Regan Boot | Black Ankle Bootie | Color: Black/Brown | Size: 6.5

Nwot, Unworn (Outside Of House); In Excellent Condition!* Cool Rich Leather Pull-On Boots With Block Heels For A Little Extra Height. Made With Mwl Cloudlift Lite Padding For Extra Comfort! Size: 6.5; Fits Tts 4 1/2" Shaft Height (Based On Size 7) 2...

Poshmark

$40.00

go to store
Madewell Shoes | Madewell Billie Leather Ankle Boot - Black Size 10 | Color: Black | Size: 10

Madewell Shoes | Madewell Billie Leather Ankle Boot - Black Size 10 | Color: Black | Size: 10

Good Used Condition Madewell Billie Boots In Black Leather. I Frequently Conditioned The Leather And Despite Some Wear To The Heels And Sole, They Have A Lot Of Life Left In Them!!! Small Nick In The Leather On The Outside Of The Right Boot. No Other... ... more

Madewell Shoes | Madewell Billie Leather Ankle Boot - Black Size 10 | Color: Black | Size: 10

Good Used Condition Madewell Billie Boots In Black Leather. I Frequently Conditioned The Leather And Despite Some Wear To The Heels And Sole, They Have A Lot Of Life Left In Them!!! Small Nick In The Leather On The Outside Of The Right Boot. No Other...

Poshmark

$22.00

go to store
Madewell Shoes | Madewell Bryce Suede Chelsea Ankle Boot Equestrian Brown Size 10 | Color: Brown | Size: 10

Madewell Shoes | Madewell Bryce Suede Chelsea Ankle Boot Equestrian Brown Size 10 | Color: Brown | Size: 10

Madewell Bryce Suede Chelsea Ankle Boot Equestrian Brown Size 10 New Without Tag Shoe Is Store Return And May Have Minor Blemish ... more

Madewell Shoes | Madewell Bryce Suede Chelsea Ankle Boot Equestrian Brown Size 10 | Color: Brown | Size: 10

Madewell Bryce Suede Chelsea Ankle Boot Equestrian Brown Size 10 New Without Tag Shoe Is Store Return And May Have Minor Blemish

Poshmark

$95.00

go to store
Madewell Shoes | Madewell Insulated Ankle Boots - Size 10 | Color: Black | Size: 10

Madewell Shoes | Madewell Insulated Ankle Boots - Size 10 | Color: Black | Size: 10

Nwot, Worn Once, In Excellent Condition, I Am Not A Reseller. All Clothing Is From My Own Collection And Is Very Well Taken Care Of. There Are No Visible Flaws. If There Are, They Will Be Mentioned And Shown In Photos Best I Can. **Please Feel Free To... ... more

Madewell Shoes | Madewell Insulated Ankle Boots - Size 10 | Color: Black | Size: 10

Nwot, Worn Once, In Excellent Condition, I Am Not A Reseller. All Clothing Is From My Own Collection And Is Very Well Taken Care Of. There Are No Visible Flaws. If There Are, They Will Be Mentioned And Shown In Photos Best I Can. **Please Feel Free To...

Poshmark

$50.00

go to store
Madewell Shoes | Madewell Leather Ankle Boots - Size 10 | Color: Brown | Size: 10

Madewell Shoes | Madewell Leather Ankle Boots - Size 10 | Color: Brown | Size: 10

Very Comfortable, Flat Boots That Will Finish A Fall Or Winter Outfit. ... more

Madewell Shoes | Madewell Leather Ankle Boots - Size 10 | Color: Brown | Size: 10

Very Comfortable, Flat Boots That Will Finish A Fall Or Winter Outfit.

Poshmark

$40.00

go to store
Madewell Shoes | Madewell Ainsley Chelsea Boot - Size 7.5 | Color: Black | Size: 7.5

Madewell Shoes | Madewell Ainsley Chelsea Boot - Size 7.5 | Color: Black | Size: 7.5

Madewell Leather Ankle Boots Gently Worn Elastic Stretch On Interior And Exterior Side Ankle Minor Scuffing On Left Shoe Shown In Photo ... more

Madewell Shoes | Madewell Ainsley Chelsea Boot - Size 7.5 | Color: Black | Size: 7.5

Madewell Leather Ankle Boots Gently Worn Elastic Stretch On Interior And Exterior Side Ankle Minor Scuffing On Left Shoe Shown In Photo

Poshmark

$50.00

go to store
Madewell Shoes | Madewell Ainsley Chelsea Ankle Booties 9.5 | Color: Cream | Size: 9.5

Madewell Shoes | Madewell Ainsley Chelsea Ankle Booties 9.5 | Color: Cream | Size: 9.5

Madewell Ainsley Chelsea Suede Boots In Size 9.5. Small Smudge On The Outside Of The Right Boot (See Picture) Otherwise In Great Condition. ... more

Madewell Shoes | Madewell Ainsley Chelsea Ankle Booties 9.5 | Color: Cream | Size: 9.5

Madewell Ainsley Chelsea Suede Boots In Size 9.5. Small Smudge On The Outside Of The Right Boot (See Picture) Otherwise In Great Condition.

Poshmark

$41.00

go to store
Madewell Shoes | Madewell Ankle Boots | Color: Black/Brown | Size: 6.5

Madewell Shoes | Madewell Ankle Boots | Color: Black/Brown | Size: 6.5

In Good Condition Size 6.5 ... more

$45.00

go to store
Madewell Shoes | Madewell Black Suede Western Style Ankle Boots | Color: Black/Brown | Size: 7.5

Madewell Shoes | Madewell Black Suede Western Style Ankle Boots | Color: Black/Brown | Size: 7.5

Madewell Barnwood Boot. Black Suede Western Style Ankle Boots. Size 7.5. Pointed Toe, Inside Zipper, And Western Style Stitching And Construction. Genuine Suede And Leather. Good Used Condition. Some Wear On The Heels, But Soles Are In Great Shape! I... ... more

Madewell Shoes | Madewell Black Suede Western Style Ankle Boots | Color: Black/Brown | Size: 7.5

Madewell Barnwood Boot. Black Suede Western Style Ankle Boots. Size 7.5. Pointed Toe, Inside Zipper, And Western Style Stitching And Construction. Genuine Suede And Leather. Good Used Condition. Some Wear On The Heels, But Soles Are In Great Shape! I...

Poshmark

$40.00

go to store
Madewell Shoes | Madewell Rosie Ankle Boot In Snake Embossed Leather | Color: Black/Brown | Size: 7.5

Madewell Shoes | Madewell Rosie Ankle Boot In Snake Embossed Leather | Color: Black/Brown | Size: 7.5

Snake Embossed Leather Perfect For Fall Winter Zippers At The Side In Good Condition Made In Brazil Size:7.5 ... more

Madewell Shoes | Madewell Rosie Ankle Boot In Snake Embossed Leather | Color: Black/Brown | Size: 7.5

Snake Embossed Leather Perfect For Fall Winter Zippers At The Side In Good Condition Made In Brazil Size:7.5

Poshmark

$20.00

go to store
Madewell Shoes | New Madewell Black Tan Gray Snake Python Embossed Leather Rosie Ankle Boot | Color: Black/Brown | Size: 6

Madewell Shoes | New Madewell Black Tan Gray Snake Python Embossed Leather Rosie Ankle Boot | Color: Black/Brown | Size: 6

Madewell Embossed Leather Upper Look No Further For Your Dream Ankle Boot. Pieced From Snake Embossed Leather, It Has A Comfy Stacked Heel And Mwl Cloudlift Lite Padding That Feels Like Walking On A...Well, You Know. Nwob 2 1/2" Heel. ... more

Madewell Shoes | New Madewell Black Tan Gray Snake Python Embossed Leather Rosie Ankle Boot | Color: Black/Brown | Size: 6

Madewell Embossed Leather Upper Look No Further For Your Dream Ankle Boot. Pieced From Snake Embossed Leather, It Has A Comfy Stacked Heel And Mwl Cloudlift Lite Padding That Feels Like Walking On A...Well, You Know. Nwob 2 1/2" Heel.

Poshmark

$42.00

go to store
Madewell Shoes | Madewell The Brenner Boot Leather Block Heels Ankle Bootie Almond Toe | Color: Black/Brown | Size: 9.5

Madewell Shoes | Madewell The Brenner Boot Leather Block Heels Ankle Bootie Almond Toe | Color: Black/Brown | Size: 9.5

Excellent Used Condition, A Couple Of Small Scuffs And Wear To Bottoms, No Major Flaws. A Never-Not-Perfect Wardrobe Mvp. In Rich, Durable Leather (Right Down To The Easy-To-Break-In Sole) With A Comfy Stacked Heelthis Is The Kind Of Boot You'll Reach... ... more

Madewell Shoes | Madewell The Brenner Boot Leather Block Heels Ankle Bootie Almond Toe | Color: Black/Brown | Size: 9.5

Excellent Used Condition, A Couple Of Small Scuffs And Wear To Bottoms, No Major Flaws. A Never-Not-Perfect Wardrobe Mvp. In Rich, Durable Leather (Right Down To The Easy-To-Break-In Sole) With A Comfy Stacked Heelthis Is The Kind Of Boot You'll Reach...

Poshmark

$32.00

go to store
Madewell Shoes | Madewell Reid Two Tone Leather Ankle Boots | Black/Chestnut 7 | Color: Black/Brown | Size: 7

Madewell Shoes | Madewell Reid Two Tone Leather Ankle Boots | Black/Chestnut 7 | Color: Black/Brown | Size: 7

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

Madewell Shoes | Madewell Reid Two Tone Leather Ankle Boots | Black/Chestnut 7 | Color: Black/Brown | Size: 7

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

Poshmark

$55.00

go to store
Madewell Shoes | Madewell Billie Leather Pull-On Ankle Boots English Saddle | Color: Brown/Tan | Size: 8

Madewell Shoes | Madewell Billie Leather Pull-On Ankle Boots English Saddle | Color: Brown/Tan | Size: 8

Size 8. Box Included. Leather Upper And Lining. Leather Is In Great Condition, Some Marks As Shown. Bottoms In Used Condition. Style Number E0191 ... more

Madewell Shoes | Madewell Billie Leather Pull-On Ankle Boots English Saddle | Color: Brown/Tan | Size: 8

Size 8. Box Included. Leather Upper And Lining. Leather Is In Great Condition, Some Marks As Shown. Bottoms In Used Condition. Style Number E0191

Poshmark

$28.00

go to store
Madewell Shoes | Madewell The Ainsley Chelsea Boot In Black Size 6 | Color: Black | Size: 6

Madewell Shoes | Madewell The Ainsley Chelsea Boot In Black Size 6 | Color: Black | Size: 6

New Without Box But They Do Show Some Scratches And Marks From Being Without Box And Around Other Shoes And From Being Tried On. Please See All Pics. Labeled Size 6. Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks... ... more

Madewell Shoes | Madewell The Ainsley Chelsea Boot In Black Size 6 | Color: Black | Size: 6

New Without Box But They Do Show Some Scratches And Marks From Being Without Box And Around Other Shoes And From Being Tried On. Please See All Pics. Labeled Size 6. Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks...

Poshmark

$99.00

go to store
Madewell Shoes | Madewell Ainsley Chelsea Boot In English Saddle, Size 8 | Color: Brown/Tan | Size: 8

Madewell Shoes | Madewell Ainsley Chelsea Boot In English Saddle, Size 8 | Color: Brown/Tan | Size: 8

"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." -4" Shaft Height (Based On Size 7) -1 3/16"... ... more

Madewell Shoes | Madewell Ainsley Chelsea Boot In English Saddle, Size 8 | Color: Brown/Tan | Size: 8

"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." -4" Shaft Height (Based On Size 7) -1 3/16"...

Poshmark

$80.00

go to store
Madewell Shoes | Madewell Ainsley Chelsea Black Leather Boots Size 9 | Color: Black | Size: 9

Madewell Shoes | Madewell Ainsley Chelsea Black Leather Boots Size 9 | 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. Leather Upper And Lining. Item Is Pre Owned And... ... more

Madewell Shoes | Madewell Ainsley Chelsea Black Leather Boots Size 9 | 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. Leather Upper And Lining. Item Is Pre Owned And...

Poshmark

$40.00

go to store
Madewell Shoes | Madewell J8295 Ainsley Chelsea Boot - Black Size 9 | Color: Black | Size: 9

Madewell Shoes | Madewell J8295 Ainsley Chelsea Boot - Black Size 9 | Color: Black | Size: 9

Only Worn A Handful Of Times, Overall Excellent Condition Except For Cracking In The Leather Sole From Storage. Made In Brazil. Fits Tts. ... more

Madewell Shoes | Madewell J8295 Ainsley Chelsea Boot - Black Size 9 | Color: Black | Size: 9

Only Worn A Handful Of Times, Overall Excellent Condition Except For Cracking In The Leather Sole From Storage. Made In Brazil. Fits Tts.

Poshmark

$40.00

go to store