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 The Ainsley Chelsea Boots Women's Size 7 Black Leather J8295 (Scuffed) | Color: Black | Size: 7

Madewell Shoes | Madewell The Ainsley Chelsea Boots Women's Size 7 Black Leather J8295 (Scuffed) | Color: Black | Size: 7

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

Madewell Shoes | Madewell The Ainsley Chelsea Boots Women's Size 7 Black Leather J8295 (Scuffed) | Color: Black | Size: 7

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

Poshmark

$25.00

go to store
Madewell Shoes | - Madewell Ainsley Chelsea Black Leather Boots | Color: Black | Size: 7

Madewell Shoes | - Madewell Ainsley Chelsea Black Leather Boots | Color: Black | Size: 7

Madewell Ainsley Chelsea Black Leather Boots True Black Leather Size 7 These Are In Great Preowned Condition Mild Scuffing Or Wear See Pictures For Details ... more

Madewell Shoes | - Madewell Ainsley Chelsea Black Leather Boots | Color: Black | Size: 7

Madewell Ainsley Chelsea Black Leather Boots True Black Leather Size 7 These Are In Great Preowned Condition Mild Scuffing Or Wear See Pictures For Details

Poshmark

$35.00

go to store
Best Seller
Madewell Shoes | Madewell The Ainsley Chelsea Boot | Women's 8.5 | Black Leather | Item J8295 | Color: Black/Tan | Size: 8.5

Madewell Shoes | Madewell The Ainsley Chelsea Boot | Women's 8.5 | Black Leather | Item J8295 | Color: Black/Tan | Size: 8.5

Madewell The Ainsley Chelsea Boot (Color: Black Leather) Women's Size 8.5 (According To Madewell Site, Fit Runs True To Size) Excellent Pre-Owned Condition (See Photos). Shoes Were Worn Less Than 5 Times- Have Some Minor Creasing In Leather And... ... more

Madewell Shoes | Madewell The Ainsley Chelsea Boot | Women's 8.5 | Black Leather | Item J8295 | Color: Black/Tan | Size: 8.5

Madewell The Ainsley Chelsea Boot (Color: Black Leather) Women's Size 8.5 (According To Madewell Site, Fit Runs True To Size) Excellent Pre-Owned Condition (See Photos). Shoes Were Worn Less Than 5 Times- Have Some Minor Creasing In Leather And...

Poshmark

$49.00

go to store
Madewell Shoes | Madewell The Ainsley Chelsea Boot J8295 Leather Size 6 | Color: Black | Size: 6

Madewell Shoes | Madewell The Ainsley Chelsea Boot J8295 Leather Size 6 | Color: Black | Size: 6

Reposhing This Item I Purchased From @Innergypsy2. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! ... more

Madewell Shoes | Madewell The Ainsley Chelsea Boot J8295 Leather Size 6 | Color: Black | Size: 6

Reposhing This Item I Purchased From @Innergypsy2. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below!

Poshmark

$60.00

go to store
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

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...

Poshmark

$50.00

go to store
Madewell Shoes | Madewell The Ainsley Brown Leather Chelsea Pull On Ankle Boots Size 8 | Color: Brown/Tan | Size: 8

Madewell Shoes | Madewell The Ainsley Brown Leather Chelsea Pull On Ankle Boots Size 8 | Color: Brown/Tan | Size: 8

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

Madewell Shoes | Madewell The Ainsley Brown Leather Chelsea Pull On Ankle Boots Size 8 | Color: Brown/Tan | Size: 8

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

Poshmark

$35.00

go to store
Madewell Shoes | Madewell Leather Chelsea Ainsley Boots Size 10 | Color: Brown | Size: 10

Madewell Shoes | Madewell Leather Chelsea Ainsley Boots Size 10 | Color: Brown | Size: 10

Well Loved But Such Quality That They Have Lots Of Life Left. Pregnancy Gave Me Bigger Feet Or Id Wear These Again! Offers Welcome. See Pics For Condition ... more

Madewell Shoes | Madewell Leather Chelsea Ainsley Boots Size 10 | Color: Brown | Size: 10

Well Loved But Such Quality That They Have Lots Of Life Left. Pregnancy Gave Me Bigger Feet Or Id Wear These Again! Offers Welcome. See Pics For Condition

Poshmark

$20.00

go to store
Madewell Shoes | Madewell Ainsley Chelsea Boot Black | Color: Black | Size: 8.5

Madewell Shoes | Madewell Ainsley Chelsea Boot Black | Color: Black | Size: 8.5

Madewell Ainsley Chelsea Boot Black Product Details Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. 2” Heel. Leather Upper And Lining. ... more

Madewell Shoes | Madewell Ainsley Chelsea Boot Black | Color: Black | Size: 8.5

Madewell Ainsley Chelsea Boot Black Product Details Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. 2” Heel. Leather Upper And Lining.

Poshmark

$128.00

go to store
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

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....

Poshmark

$40.00

go to store
Madewell Shoes | Nwb Madewell Chelsea Leather Boots Sz 7 Made In Brazil True Black | Color: Black | Size: 7

Madewell Shoes | Nwb Madewell Chelsea Leather Boots Sz 7 Made In Brazil True Black | Color: Black | Size: 7

New With Box. Bought In 2015 But Never Wore. I'm A 7-7.5 And I'd Say These Fit True To Size ... more

Madewell Shoes | Nwb Madewell Chelsea Leather Boots Sz 7 Made In Brazil True Black | Color: Black | Size: 7

New With Box. Bought In 2015 But Never Wore. I'm A 7-7.5 And I'd Say These Fit True To Size

Poshmark

$90.00

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

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

Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cloudlift Lite Padding Make These Really Comfortable To Walk In Or Wear All Day. 4" Shaft Height (Based On Size 7). 1 3/16" Heel. ... more

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

Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cloudlift Lite Padding Make These Really Comfortable To Walk In Or Wear All Day. 4" Shaft Height (Based On Size 7). 1 3/16" Heel.

Poshmark

$63.00

go to store
Madewell Shoes | Madewell "Ainsley Chelsea" In Spotted Calf Hair Ankle Boot Size 6 | Color: Black | Size: 6

Madewell Shoes | Madewell "Ainsley Chelsea" In Spotted Calf Hair Ankle Boot Size 6 | Color: Black | Size: 6

Madewell "Ainsley Chelsea" In Spotted Calf Hair Ankle Boot Size 6 1 3/16" Heel Calf Hair Upper Man-Made Sole ... more

Madewell Shoes | Madewell "Ainsley Chelsea" In Spotted Calf Hair Ankle Boot Size 6 | Color: Black | Size: 6

Madewell "Ainsley Chelsea" In Spotted Calf Hair Ankle Boot Size 6 1 3/16" Heel Calf Hair Upper Man-Made Sole

Poshmark

$25.00

go to store
Madewell Shoes | Madewell Ainsley Chelsea Ankle Boots Size 6 | Color: Black/Brown | Size: 6

Madewell Shoes | Madewell Ainsley Chelsea Ankle Boots Size 6 | Color: Black/Brown | Size: 6

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

Madewell Shoes | Madewell Ainsley Chelsea Ankle Boots Size 6 | Color: Black/Brown | Size: 6

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

Poshmark

$27.00

go to store
Madewell Shoes | Madewell Ainsley Chelsea Boots Leather 7.5 | Color: Brown | Size: 7.5

Madewell Shoes | Madewell Ainsley Chelsea Boots Leather 7.5 | Color: Brown | Size: 7.5

Madewell Ainsley Chelsea Boots Leather Size 7.5 Style# J8295 ... more

Madewell Shoes | Madewell Ainsley Chelsea Boots Leather 7.5 | Color: Brown | Size: 7.5

Madewell Ainsley Chelsea Boots Leather Size 7.5 Style# J8295

Poshmark

$30.00

go to store
Madewell Shoes | Madewell-Woman’s Ainsley Brown Leather Chelsea Boot | Color: Brown/Tan | Size: 9.5

Madewell Shoes | Madewell-Woman’s Ainsley Brown Leather Chelsea Boot | Color: Brown/Tan | Size: 9.5

A Closet Classic, Ainsley Brown Leather Boot Chelsea Boot. Worn But Still Structured. No Tears And Scuffs On Leather. ... more

Madewell Shoes | Madewell-Woman’s Ainsley Brown Leather Chelsea Boot | Color: Brown/Tan | Size: 9.5

A Closet Classic, Ainsley Brown Leather Boot Chelsea Boot. Worn But Still Structured. No Tears And Scuffs On Leather.

Poshmark

$20.00

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

Madewell Shoes | Madewell The Ainsley Chelsea Boot | Color: Black | Size: 6.5

Reposhing From @Styleforumdeals. I Bought These In Almost New Condition And They Have Some Wear But Are Still In Great Condition. I Had The Toe Of The Boots Re-Soled A Few Months Ago. From Website: Crafted From Buttery Leather, This Updated Chelsea... ... more

Madewell Shoes | Madewell The Ainsley Chelsea Boot | Color: Black | Size: 6.5

Reposhing From @Styleforumdeals. I Bought These In Almost New Condition And They Have Some Wear But Are Still In Great Condition. I Had The Toe Of The Boots Re-Soled A Few Months Ago. From Website: Crafted From Buttery Leather, This Updated Chelsea...

Poshmark

$70.00

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

Madewell Shoes | Madewell Ainsley Chelsea Boots | Color: Black | Size: 6

Brand New Pair Or Madewell Ainsley Chelsea Boots. Very Comfortable And Leather Stretches Out With Time. I Bought Two Pairs At Full Price Because I Loved Them So Much But These Last. I Don’t Think I Need The Second Pair Since My First One Is Going So... ... more

Madewell Shoes | Madewell Ainsley Chelsea Boots | Color: Black | Size: 6

Brand New Pair Or Madewell Ainsley Chelsea Boots. Very Comfortable And Leather Stretches Out With Time. I Bought Two Pairs At Full Price Because I Loved Them So Much But These Last. I Don’t Think I Need The Second Pair Since My First One Is Going So...

Poshmark

$175.00

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

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

Size 6 No Box 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"... ... more

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

Size 6 No Box 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"...

Poshmark

$60.00

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 Ainsley Chelsea Boot | Color: Black | Size: 7.5

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

Barely Worn! Ordered From Madewell. 7.5 True To Size. ... more

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

Barely Worn! Ordered From Madewell. 7.5 True To Size.

Poshmark

$100.00

go to store
Madewell Shoes | Madewell | The Regan Boot In Black, Chelsea Boot W/ Almond Toe, Block Heel Sz. 9 | Color: Black | Size: 9

Madewell Shoes | Madewell | The Regan Boot In Black, Chelsea Boot W/ Almond Toe, Block Heel Sz. 9 | Color: Black | Size: 9

Brand: Madewell Style: The Regan Boot In Black Size: 9 Condition: Very Good. Details: Genuine Leather Bootie. Slip-On Style. Pointed Almond Toe. From The Madewell Website: Made Of Rich Leather, These Cool Pull-On Boots Have Block Heels For A Little... ... more

Madewell Shoes | Madewell | The Regan Boot In Black, Chelsea Boot W/ Almond Toe, Block Heel Sz. 9 | Color: Black | Size: 9

Brand: Madewell Style: The Regan Boot In Black Size: 9 Condition: Very Good. Details: Genuine Leather Bootie. Slip-On Style. Pointed Almond Toe. From The Madewell Website: Made Of Rich Leather, These Cool Pull-On Boots Have Block Heels For A Little...

Poshmark

$65.00

go to store
Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Black | Size: 8.5

Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Black | Size: 8.5

Good Used Condition - See Photos. ... more

$40.00

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

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

Guc It Has Signs Of Wear Heel Height Is 1 Tall Keywords Boho Chic Slouchy Boxy On Trend Work Office Women Men Kid Hipster Stylish Fall Autumn Winter Spring Summer Vintage Retro 80s 90s Vacation Chunky Cozy Goth Classic Minimalist Staple Layer Street... ... more

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

Guc It Has Signs Of Wear Heel Height Is 1 Tall Keywords Boho Chic Slouchy Boxy On Trend Work Office Women Men Kid Hipster Stylish Fall Autumn Winter Spring Summer Vintage Retro 80s 90s Vacation Chunky Cozy Goth Classic Minimalist Staple Layer Street...

Poshmark

$69.00

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 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 Ainsley Chelsea Boot | Color: Brown | Size: 8

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

Leather Size 8 Chelsea Boots From Madewell. They Have Been Loved And Worn, Please Note The Signs Of Wear. These Boots Are Super Well Made And Feel Great! ... more

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

Leather Size 8 Chelsea Boots From Madewell. They Have Been Loved And Worn, Please Note The Signs Of Wear. These Boots Are Super Well Made And Feel Great!

Poshmark

$80.00

go to store
Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Orange/Tan | Size: 6

Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Orange/Tan | Size: 6

The Ainsley Chelsea Boot In English Saddle Brown. 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... ... more

Madewell Shoes | Madewell Ainsley Chelsea Boot | Color: Orange/Tan | Size: 6

The Ainsley Chelsea Boot In English Saddle Brown. 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...

Poshmark

$80.00

go to store
Madewell Shoes | Madewell Short Stacked-Heel Chelsea Boots, Black, Sz 6.5 | Color: Black | Size: 6.5

Madewell Shoes | Madewell Short Stacked-Heel Chelsea Boots, Black, Sz 6.5 | Color: Black | Size: 6.5

Madewell Short Stacked-Heel Chelsea Boots, Black, Sz 6.5 Women's Size 6.5 Color Black Cleaning Out Closet Worn A Handful Of Times In Great Condition Smoke Free Home All Sales Final ... more

Madewell Shoes | Madewell Short Stacked-Heel Chelsea Boots, Black, Sz 6.5 | Color: Black | Size: 6.5

Madewell Short Stacked-Heel Chelsea Boots, Black, Sz 6.5 Women's Size 6.5 Color Black Cleaning Out Closet Worn A Handful Of Times In Great Condition Smoke Free Home All Sales Final

Poshmark

$100.00

go to store
Madewell Shoes | Madewell The Elspeth Chelsea Boots Sz 12 Black (Heels Protective Covered) | Color: Black | Size: 12

Madewell Shoes | Madewell The Elspeth Chelsea Boots Sz 12 Black (Heels Protective Covered) | Color: Black | Size: 12

Madewell The Elspeth Chelsea Boots Sz 12 Black (Heels Protective Covered). Excellent Condition ... more

Madewell Shoes | Madewell The Elspeth Chelsea Boots Sz 12 Black (Heels Protective Covered) | Color: Black | Size: 12

Madewell The Elspeth Chelsea Boots Sz 12 Black (Heels Protective Covered). Excellent Condition

Poshmark

$75.00

go to store
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

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...

Poshmark

$50.00

go to store
Madewell Shoes | ! Madewell $198 The Ainsley Chelsea Boots G8421 | Color: Tan | Size: 8

Madewell Shoes | ! Madewell $198 The Ainsley Chelsea Boots G8421 | Color: Tan | Size: 8

Madewell $198 The Ainsley Chelsea Boots In Suede G8421 8 Natural In Soft Suede, With Easy-To-Break-In Leather Soles, This Modern Chelsea Boot Has A Pared Down Look That Makes It A Design-Team Favorite. Meet Your New Wardrobe Mvp. Please Note: When You... ... more

Madewell Shoes | ! Madewell $198 The Ainsley Chelsea Boots G8421 | Color: Tan | Size: 8

Madewell $198 The Ainsley Chelsea Boots In Suede G8421 8 Natural In Soft Suede, With Easy-To-Break-In Leather Soles, This Modern Chelsea Boot Has A Pared Down Look That Makes It A Design-Team Favorite. Meet Your New Wardrobe Mvp. Please Note: When You...

Poshmark

$47.00

go to store
Madewell Shoes | Madewell The Elspeth Chelsea Boots Sz 12 Black (Heels Protective Covered) | Color: Black | Size: 12

Madewell Shoes | Madewell The Elspeth Chelsea Boots Sz 12 Black (Heels Protective Covered) | Color: Black | Size: 12

Madewell The Elspeth Chelsea Boots Sz 12 Black (Heels Protective Covered). Excellent Condition ... more

Madewell Shoes | Madewell The Elspeth Chelsea Boots Sz 12 Black (Heels Protective Covered) | Color: Black | Size: 12

Madewell The Elspeth Chelsea Boots Sz 12 Black (Heels Protective Covered). Excellent Condition

Poshmark

$89.00

go to store
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

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...

Poshmark

$45.00

go to store
Madewell Shoes | Madewell Spencer Chelsea Leather Ankle Boot, Sz 8 | Color: Tan/Brown | Size: 8

Madewell Shoes | Madewell Spencer Chelsea Leather Ankle Boot, Sz 8 | Color: Tan/Brown | Size: 8

Madewell Spencer Chelsea Leather Ankle Boot, Sz 8 ... more

$47.00

go to store
Madewell Shoes | Madewell The Camryn Chelsea Boot In Leather Sz 6.5 Nh205 | Color: Brown | Size: 6.5

Madewell Shoes | Madewell The Camryn Chelsea Boot In Leather Sz 6.5 Nh205 | Color: Brown | Size: 6.5

Preowned, Small Hole In Elastic Part On Right Boot See Pics Lightweight And Comfy, This Classic Leather Chelsea Boot Has Updated Thick Weather-Sealed Rubber Soles Ready To Take On Whatever The Day Bringsrain Included. Sock-Like Elastic Insets Make... ... more

Madewell Shoes | Madewell The Camryn Chelsea Boot In Leather Sz 6.5 Nh205 | Color: Brown | Size: 6.5

Preowned, Small Hole In Elastic Part On Right Boot See Pics Lightweight And Comfy, This Classic Leather Chelsea Boot Has Updated Thick Weather-Sealed Rubber Soles Ready To Take On Whatever The Day Bringsrain Included. Sock-Like Elastic Insets Make...

Poshmark

$40.00

go to store
Madewell Shoes | Madewell Ainsley Chelsea Boot Nwt | Color: Tan | Size: 8.5

Madewell Shoes | Madewell Ainsley Chelsea Boot Nwt | Color: Tan | Size: 8.5

Nib! Realized I Bought A Backup Pair That I Never Wore Def Takes A Bit To Break In But End Up So Comfortable “Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: Our Mwl... ... more

Madewell Shoes | Madewell Ainsley Chelsea Boot Nwt | Color: Tan | Size: 8.5

Nib! Realized I Bought A Backup Pair That I Never Wore Def Takes A Bit To Break In But End Up So Comfortable “Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: Our Mwl...

Poshmark

$120.00

go to store
Madewell Shoes | Madewell Regan Taupe Suede Leather Stacked Heel Ankle Chelsea Boots Sz 9.5 | Color: Gray/Tan | Size: 9.5

Madewell Shoes | Madewell Regan Taupe Suede Leather Stacked Heel Ankle Chelsea Boots Sz 9.5 | Color: Gray/Tan | Size: 9.5

Taupe Suede Heeled Chelsea Boots From Madewell. Worn Only A Couple Times And Still In Excellent Condition. Very Cute And Great For Fall! Size 9.5 Please Let Me Know If You Have Any Questions Or Would Like Additional Photos. ... more

Madewell Shoes | Madewell Regan Taupe Suede Leather Stacked Heel Ankle Chelsea Boots Sz 9.5 | Color: Gray/Tan | Size: 9.5

Taupe Suede Heeled Chelsea Boots From Madewell. Worn Only A Couple Times And Still In Excellent Condition. Very Cute And Great For Fall! Size 9.5 Please Let Me Know If You Have Any Questions Or Would Like Additional Photos.

Poshmark

$75.00

go to store
Madewell Shoes | Madewell The Toasty Leather Upper Faux Fur Lined Chelsea Boots Sz 9*Runs Big(10) | Color: Tan | Size: 10

Madewell Shoes | Madewell The Toasty Leather Upper Faux Fur Lined Chelsea Boots Sz 9*Runs Big(10) | Color: Tan | Size: 10

Madewell The Toasty Chelsea Boots Women's 9 But Runs Big So Closer To A 10. Excellent Used Condition. $178 New Description From Madewell.Com "Product Details Lined In Faux Shearling, This Pull-On Chelsea Boot Feels Like A Slipper, But With A... ... more

Madewell Shoes | Madewell The Toasty Leather Upper Faux Fur Lined Chelsea Boots Sz 9*Runs Big(10) | Color: Tan | Size: 10

Madewell The Toasty Chelsea Boots Women's 9 But Runs Big So Closer To A 10. Excellent Used Condition. $178 New Description From Madewell.Com "Product Details Lined In Faux Shearling, This Pull-On Chelsea Boot Feels Like A Slipper, But With A...

Poshmark

$65.00

go to store
Madewell Shoes | Madewell Cleary Chelsea Boot In Leather, Sz 7, Nh206 | Color: Brown/Orange | Size: Various

Madewell Shoes | Madewell Cleary Chelsea Boot In Leather, Sz 7, Nh206 | Color: Brown/Orange | Size: Various

Nwob Color English Saddle Step Out This Season In A Classic Chelsea Boot, Made Of Supersmooth Leather. Designed With Durable Rubber Soles And Elastic Insets For Easy On-And-Offs, You'll Want To Wear This Versatile Pair All The Time. And, Cushiness... ... more

Madewell Shoes | Madewell Cleary Chelsea Boot In Leather, Sz 7, Nh206 | Color: Brown/Orange | Size: Various

Nwob Color English Saddle Step Out This Season In A Classic Chelsea Boot, Made Of Supersmooth Leather. Designed With Durable Rubber Soles And Elastic Insets For Easy On-And-Offs, You'll Want To Wear This Versatile Pair All The Time. And, Cushiness...

Poshmark

$118.00

go to store