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
Men's Big Easy Drew Shoe by Drew in Dark Brown Calf (Size 8 1/2 4W)

Men's Big Easy Drew Shoe by Drew in Dark Brown Calf (Size 8 1/2 4W)

The most comfortable boot weve ever made. Big Easy by Drew® combines a one-pieceadjustableclosure with a sleek boot design. Its easy to wear, durable and comfortable. Two removable insoles allow for customization. The shoes extended medial heel... ... more

Men's Big Easy Drew Shoe by Drew in Dark Brown Calf (Size 8 1/2 4W)

The most comfortable boot weve ever made. Big Easy by Drew® combines a one-pieceadjustableclosure with a sleek boot design. Its easy to wear, durable and comfortable. Two removable insoles allow for customization. The shoes extended medial heel...

KingSize Direct

$225.99

go to store
Men's Big Easy Drew Shoe by Drew in Dark Brown Calf (Size 8 1/2 6E)

Men's Big Easy Drew Shoe by Drew in Dark Brown Calf (Size 8 1/2 6E)

The most comfortable boot weve ever made. Big Easy by Drew® combines a one-pieceadjustableclosure with a sleek boot design. Its easy to wear, durable and comfortable. Two removable insoles allow for customization. The shoes extended medial heel... ... more

Men's Big Easy Drew Shoe by Drew in Dark Brown Calf (Size 8 1/2 6E)

The most comfortable boot weve ever made. Big Easy by Drew® combines a one-pieceadjustableclosure with a sleek boot design. Its easy to wear, durable and comfortable. Two removable insoles allow for customization. The shoes extended medial heel...

KingSize Direct

$225.99

go to store
Best Seller
Wide Width Men's Big Easy Drew Shoe by Drew in Dark Brown Calf (Size 8 1/2 W)

Wide Width Men's Big Easy Drew Shoe by Drew in Dark Brown Calf (Size 8 1/2 W)

The most comfortable boot weve ever made. Big Easy by Drew® combines a one-pieceadjustableclosure with a sleek boot design. Its easy to wear, durable and comfortable. Two removable insoles allow for customization. The shoes extended medial heel... ... more

Wide Width Men's Big Easy Drew Shoe by Drew in Dark Brown Calf (Size 8 1/2 W)

The most comfortable boot weve ever made. Big Easy by Drew® combines a one-pieceadjustableclosure with a sleek boot design. Its easy to wear, durable and comfortable. Two removable insoles allow for customization. The shoes extended medial heel...

KingSize Direct

$225.99

go to store
Madewell Shoes | Madewell Grayson Brogue Chelsea Boots, Size 8 1/2 | Color: Brown/Tan | Size: 8.5

Madewell Shoes | Madewell Grayson Brogue Chelsea Boots, Size 8 1/2 | Color: Brown/Tan | Size: 8.5

Great Used Condition Only Worn Once Since They Don't Fit Me Top Rated On Madewell! ... more

Madewell Shoes | Madewell Grayson Brogue Chelsea Boots, Size 8 1/2 | Color: Brown/Tan | Size: 8.5

Great Used Condition Only Worn Once Since They Don't Fit Me Top Rated On Madewell!

Poshmark

$65.00

go to store
Madewell Shoes | Madewell Sonia Low Chelsea Boot Size 7 1/2 Snake Embossed Leather | Color: Brown/White | Size: 7.5

Madewell Shoes | Madewell Sonia Low Chelsea Boot Size 7 1/2 Snake Embossed Leather | Color: Brown/White | Size: 7.5

Madewell Sonia Low Chelsea Boot Size 8 Snake Embossed Leather Beautiful Leather Ankle Boot Reposhing Because Too Small Size 8 But Runs Small I’m A True Size 8 Feels More Like A 7 / 7 1/2 Look Brand New Soles Look Never Worn ... more

Madewell Shoes | Madewell Sonia Low Chelsea Boot Size 7 1/2 Snake Embossed Leather | Color: Brown/White | Size: 7.5

Madewell Sonia Low Chelsea Boot Size 8 Snake Embossed Leather Beautiful Leather Ankle Boot Reposhing Because Too Small Size 8 But Runs Small I’m A True Size 8 Feels More Like A 7 / 7 1/2 Look Brand New Soles Look Never Worn

Poshmark

$35.00

go to store
Men's Daily Double Chelsea Boots by Eastland® in Dark Brown (Size 9 1/2 M)

Men's Daily Double Chelsea Boots by Eastland® in Dark Brown (Size 9 1/2 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... ... more

Men's Daily Double Chelsea Boots by Eastland® in Dark Brown (Size 9 1/2 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability....

OneStopPlus

$125.00

go to store
Men's Boulder Drew Shoe by Drew in Dark Brown (Size 8 1/2 4W)

Men's Boulder Drew Shoe by Drew in Dark Brown (Size 8 1/2 4W)

Drew® proudly presents the Boulder, a lower-cut version of the popular Rockford boot for men. The Boulder has double the added depth. Ideal for extra-thick orthotics, or extreme foot conditions. Waterproof leather upper and lining. And it's... ... more

Men's Boulder Drew Shoe by Drew in Dark Brown (Size 8 1/2 4W)

Drew® proudly presents the Boulder, a lower-cut version of the popular Rockford boot for men. The Boulder has double the added depth. Ideal for extra-thick orthotics, or extreme foot conditions. Waterproof leather upper and lining. And it's...

OneStopPlus

$260.99

go to store
Wide Width Men's Propet Sentry Men'S Work Boots Shoes by Propet in Black (Size 8 1/2 W)

Wide Width Men's Propet Sentry Men'S Work Boots Shoes by Propet in Black (Size 8 1/2 W)

Waterproof bootie construction inside a Crazy horse leather and nylon mesh upper with padded collar and tongue and abrasion resistant rubber toe cap. Embedded Puncture resistant insole plus removable Open Cell insole that moves moisture from foot for a... ... more

Wide Width Men's Propet Sentry Men'S Work Boots Shoes by Propet in Black (Size 8 1/2 W)

Waterproof bootie construction inside a Crazy horse leather and nylon mesh upper with padded collar and tongue and abrasion resistant rubber toe cap. Embedded Puncture resistant insole plus removable Open Cell insole that moves moisture from foot for a...

OneStopPlus

$129.99

go to store
Men's Boulder Drew Shoe by Drew in Dark Brown (Size 8 1/2 4W)

Men's Boulder Drew Shoe by Drew in Dark Brown (Size 8 1/2 4W)

Drew® proudly presents the Boulder, a lower-cut version of the popular Rockford boot for men. The Boulder has double the added depth. Ideal for extra-thick orthotics, or extreme foot conditions. Waterproof leather upper and lining. And it's... ... more

Men's Boulder Drew Shoe by Drew in Dark Brown (Size 8 1/2 4W)

Drew® proudly presents the Boulder, a lower-cut version of the popular Rockford boot for men. The Boulder has double the added depth. Ideal for extra-thick orthotics, or extreme foot conditions. Waterproof leather upper and lining. And it's...

KingSize Direct

$260.99

go to store
Men's Tucson Drew Shoe by Drew in Black Calf (Size 8 1/2 6E)

Men's Tucson Drew Shoe by Drew in Black Calf (Size 8 1/2 6E)

Tucson by Drew® is a sleek pebbled leather boot thats durable, great-looking and therapeutically beneficial. Tucson offers two removable insoles. Keep both in for added depth. Remove one for double added depth. Provides extra control of the gait cycle... ... more

Men's Tucson Drew Shoe by Drew in Black Calf (Size 8 1/2 6E)

Tucson by Drew® is a sleek pebbled leather boot thats durable, great-looking and therapeutically beneficial. Tucson offers two removable insoles. Keep both in for added depth. Remove one for double added depth. Provides extra control of the gait cycle...

KingSize Direct

$225.99

go to store
Men's Murphy Casual Boots by Drew in Camel Leather (Size 8 1/2 4W)

Men's Murphy Casual Boots by Drew in Camel Leather (Size 8 1/2 4W)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The... ... more

Men's Murphy Casual Boots by Drew in Camel Leather (Size 8 1/2 4W)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The...

KingSize Direct

$286.99

go to store
Men's Boulder Drew Shoe by Drew in Dark Brown (Size 9 1/2 4W)

Men's Boulder Drew Shoe by Drew in Dark Brown (Size 9 1/2 4W)

Drew® proudly presents the Boulder, a lower-cut version of the popular Rockford boot for men. The Boulder has double the added depth. Ideal for extra-thick orthotics, or extreme foot conditions. Waterproof leather upper and lining. And it's... ... more

Men's Boulder Drew Shoe by Drew in Dark Brown (Size 9 1/2 4W)

Drew® proudly presents the Boulder, a lower-cut version of the popular Rockford boot for men. The Boulder has double the added depth. Ideal for extra-thick orthotics, or extreme foot conditions. Waterproof leather upper and lining. And it's...

KingSize Direct

$260.99

go to store
Wide Width Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 8 1/2 W)

Wide Width Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 8 1/2 W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew... ... more

Wide Width Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 8 1/2 W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew...

KingSize Direct

$224.99

go to store
Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 8 1/2 4W)

Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 8 1/2 4W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew... ... more

Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 8 1/2 4W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew...

KingSize Direct

$224.99

go to store
Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 9 1/2 4W)

Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 9 1/2 4W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew... ... more

Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 9 1/2 4W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew...

KingSize Direct

$224.99

go to store
Wide Width Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 9 1/2 W)

Wide Width Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 9 1/2 W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew... ... more

Wide Width Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 9 1/2 W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew...

KingSize Direct

$224.99

go to store
Wide Width Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 11 1/2 W)

Wide Width Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 11 1/2 W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew... ... more

Wide Width Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 11 1/2 W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew...

KingSize Direct

$224.99

go to store
Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 10 1/2 4W)

Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 10 1/2 4W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew... ... more

Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 10 1/2 4W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew...

KingSize Direct

$224.99

go to store
Wide Width Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 10 1/2 W)

Wide Width Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 10 1/2 W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew... ... more

Wide Width Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 10 1/2 W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew...

KingSize Direct

$224.99

go to store
Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 8 4W)

Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 8 4W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew... ... more

Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 8 4W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew...

KingSize Direct

$224.99

go to store
Wide Width Men's Tucson Drew Shoe by Drew in Black Calf (Size 8 1/2 W)

Wide Width Men's Tucson Drew Shoe by Drew in Black Calf (Size 8 1/2 W)

Tucson by Drew® is a sleek pebbled leather boot thats durable, great-looking and therapeutically beneficial. Tucson offers two removable insoles. Keep both in for added depth. Remove one for double added depth. Provides extra control of the gait cycle... ... more

Wide Width Men's Tucson Drew Shoe by Drew in Black Calf (Size 8 1/2 W)

Tucson by Drew® is a sleek pebbled leather boot thats durable, great-looking and therapeutically beneficial. Tucson offers two removable insoles. Keep both in for added depth. Remove one for double added depth. Provides extra control of the gait cycle...

KingSize Direct

$225.99

go to store
Madewell Shoes | Madewell The Cleary Chelsea Boot In Tan Brown Leather 9 1/2 | Color: Brown | Size: 9.5

Madewell Shoes | Madewell The Cleary Chelsea Boot In Tan Brown Leather 9 1/2 | Color: Brown | Size: 9.5

Brand Madewell Size 9.5 Color Tan Brown Leather Made In Brazil Style # E2334 Good Used Condition. Some Wear On Heels And Front Toes. ... more

Madewell Shoes | Madewell The Cleary Chelsea Boot In Tan Brown Leather 9 1/2 | Color: Brown | Size: 9.5

Brand Madewell Size 9.5 Color Tan Brown Leather Made In Brazil Style # E2334 Good Used Condition. Some Wear On Heels And Front Toes.

Poshmark

$36.00

go to store
Madewell Shoes | Madewell 1937 Orange Leather Almanac Heels Boots, Size 8 1/2 | Color: Brown/Orange | Size: 8.5

Madewell Shoes | Madewell 1937 Orange Leather Almanac Heels Boots, Size 8 1/2 | Color: Brown/Orange | Size: 8.5

Madewell 1937 Orange Leather Almanac Heels Boots, Size 8 1/2 *Condition: Excellent Used Condition, Minor Scuffs And Darken Slot On Right Front, No Rips Or Stains. See All Pics For Wear. Sorry, No Trades. Note: The Digital Images Displayed Have The Most... ... more

Madewell Shoes | Madewell 1937 Orange Leather Almanac Heels Boots, Size 8 1/2 | Color: Brown/Orange | Size: 8.5

Madewell 1937 Orange Leather Almanac Heels Boots, Size 8 1/2 *Condition: Excellent Used Condition, Minor Scuffs And Darken Slot On Right Front, No Rips Or Stains. See All Pics For Wear. Sorry, No Trades. Note: The Digital Images Displayed Have The Most...

Poshmark

$39.00

go to store
Madewell Shoes | Madewell Black Leather Ankle Boot Sz 8 1/2 | Color: Black/Tan | Size: 8.5

Madewell Shoes | Madewell Black Leather Ankle Boot Sz 8 1/2 | Color: Black/Tan | Size: 8.5

Black Leather Ankle Boot With Zip Opening Chunky Wooden Heel Approx 3” Minimal Wear On The Body Round Toe Sole Has Some Wear Preowned But In Good Condition ... more

Madewell Shoes | Madewell Black Leather Ankle Boot Sz 8 1/2 | Color: Black/Tan | Size: 8.5

Black Leather Ankle Boot With Zip Opening Chunky Wooden Heel Approx 3” Minimal Wear On The Body Round Toe Sole Has Some Wear Preowned But In Good Condition

Poshmark

$40.00

go to store
Madewell Shoes | 1937 Madewell The Sidewalk Skimmer Brown Leather Flat Shoe - Size 7 1/2 | Color: Brown/Orange | Size: 7.5

Madewell Shoes | 1937 Madewell The Sidewalk Skimmer Brown Leather Flat Shoe - Size 7 1/2 | Color: Brown/Orange | Size: 7.5

1937 Madewell The Sidewalk Skimmer Brown Leather Flat Shoe - Size 7 1/2 Retail Price $108.00 A True Shoe Icon. You Can Wear This Sharply Shaped Flat For Miles And Milesand Never Get Tired Of Its Chic Parisian-Girl Charm. * Leather Upper. * Leather... ... more

Madewell Shoes | 1937 Madewell The Sidewalk Skimmer Brown Leather Flat Shoe - Size 7 1/2 | Color: Brown/Orange | Size: 7.5

1937 Madewell The Sidewalk Skimmer Brown Leather Flat Shoe - Size 7 1/2 Retail Price $108.00 A True Shoe Icon. You Can Wear This Sharply Shaped Flat For Miles And Milesand Never Get Tired Of Its Chic Parisian-Girl Charm. * Leather Upper. * Leather...

Poshmark

$65.00

go to store
Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 11 1/2 4W)

Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 11 1/2 4W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew... ... more

Men's Murphy Flats And Slip Ons by Drew in Dark Brown Leather (Size 11 1/2 4W)

Drew Murphy is a casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The Drew...

KingSize Direct

$224.99

go to store
Madewell Shoes | Madewell Shoes Madewell The Toasty Sherpa Tan Chelsea Boot 8 | Color: Tan | Size: 8

Madewell Shoes | Madewell Shoes Madewell The Toasty Sherpa Tan Chelsea Boot 8 | Color: Tan | Size: 8

Size 8 But Runs Big Can Fit A Size 9 In Great Pre Owned Condition ... more

$120.00

go to store
Madewell Shoes | Madewell Flats Size 8 1/2 | Color: Tan | Size: 8.5

Madewell Shoes | Madewell Flats Size 8 1/2 | Color: Tan | Size: 8.5

Tan Madewell Flats . All Flaws Photographed But Overall Very Good Condition. Wish They Fit Me . ... more

Madewell Shoes | Madewell Flats Size 8 1/2 | Color: Tan | Size: 8.5

Tan Madewell Flats . All Flaws Photographed But Overall Very Good Condition. Wish They Fit Me .

Poshmark

$30.00

go to store
Madewell Shoes | Madewell Short Boots Size 8 1/2 | Color: Black | Size: 8.5

Madewell Shoes | Madewell Short Boots Size 8 1/2 | Color: Black | Size: 8.5

Madewell Ankle Boots. Size 8 1/2, Fit True To Size. Side Zip ... more

Madewell Shoes | Madewell Short Boots Size 8 1/2 | Color: Black | Size: 8.5

Madewell Ankle Boots. Size 8 1/2, Fit True To Size. Side Zip

Poshmark

$75.00

go to store
Madewell Shoes | Madewell Size 7 1/2 Black Leather Flat Sandals | Color: Black | Size: 7.5

Madewell Shoes | Madewell Size 7 1/2 Black Leather Flat Sandals | Color: Black | Size: 7.5

Reposhing This Item I Purchased From @Jessidenver. Loved It, But Fit A Little Larger And I'm A True 7.5. Would Be Good For A Size 8! Questions? Leave A Comment Below! ... more

Madewell Shoes | Madewell Size 7 1/2 Black Leather Flat Sandals | Color: Black | Size: 7.5

Reposhing This Item I Purchased From @Jessidenver. Loved It, But Fit A Little Larger And I'm A True 7.5. Would Be Good For A Size 8! Questions? Leave A Comment Below!

Poshmark

$18.00

go to store
Madewell Shoes | Madewell The Ainsley Chelsea Boot Black Leather Size 8 | Color: Black | Size: 8

Madewell Shoes | Madewell The Ainsley Chelsea Boot Black Leather Size 8 | Color: Black | Size: 8

Madewell The Ainsley Chelsea Boot Size 8 Black Leather 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 The Ainsley Chelsea Boot Black Leather Size 8 | Color: Black | Size: 8

Madewell The Ainsley Chelsea Boot Size 8 Black Leather 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

$54.00

go to store
Madewell Shoes | Madewell Low Chelsea Boots In Snakeskin Embossed Leather Size 8 | Color: Black/Cream | Size: 8

Madewell Shoes | Madewell Low Chelsea Boots In Snakeskin Embossed Leather Size 8 | Color: Black/Cream | Size: 8

Reposhing This Item I Purchased From @Thehive3203. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! ... more

Madewell Shoes | Madewell Low Chelsea Boots In Snakeskin Embossed Leather Size 8 | Color: Black/Cream | Size: 8

Reposhing This Item I Purchased From @Thehive3203. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below!

Poshmark

$50.00

go to store
Madewell Shoes | Madewell Bonham Chelsea Boot (Brown Leather) Size 8.5 | Color: Brown | Size: 8.5

Madewell Shoes | Madewell Bonham Chelsea Boot (Brown Leather) Size 8.5 | Color: Brown | Size: 8.5

Condition: Good Pre-Owned Condition; Normal Wear & Tear On Leather And On Bottom As Shown. *Pet-Free & Smoke-Free Home* *Please Note* All Photos Taken On Iphone; Slight Color Variations Possible - All Phones/Computers Display Differently *Bundle For... ... more

Madewell Shoes | Madewell Bonham Chelsea Boot (Brown Leather) Size 8.5 | Color: Brown | Size: 8.5

Condition: Good Pre-Owned Condition; Normal Wear & Tear On Leather And On Bottom As Shown. *Pet-Free & Smoke-Free Home* *Please Note* All Photos Taken On Iphone; Slight Color Variations Possible - All Phones/Computers Display Differently *Bundle For...

Poshmark

$28.00

go to store
Madewell Shoes | Madewell Hadley Leather Boots In Wine Size 9 1/2 | Color: Black/Brown/Red | Size: 9.5

Madewell Shoes | Madewell Hadley Leather Boots In Wine Size 9 1/2 | Color: Black/Brown/Red | Size: 9.5

Excellent Used Condition Madewell Hadley Leather Boots In Wine. A Dark Brownish Red Almost Black Color This Sexy Tomboy Boot Combines A Beautifully Burnished Cordovan Finish With A Sleek Feminine Silhouette. Cordovan Leather Upper. 3 1/2" Stacked Heel.... ... more

Madewell Shoes | Madewell Hadley Leather Boots In Wine Size 9 1/2 | Color: Black/Brown/Red | Size: 9.5

Excellent Used Condition Madewell Hadley Leather Boots In Wine. A Dark Brownish Red Almost Black Color This Sexy Tomboy Boot Combines A Beautifully Burnished Cordovan Finish With A Sleek Feminine Silhouette. Cordovan Leather Upper. 3 1/2" Stacked Heel....

Poshmark

$30.00

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 Shoes Madewell Sonia Chelsea Boot Black Leather Nib | Color: Black | Size: 7

Madewell Shoes | Madewell Shoes Madewell Sonia Chelsea Boot Black Leather Nib | Color: Black | Size: 7

Madewell Shoes Madewell Sonia Chelsea Boot Black Leather Nib Sold Out! Retail $188 ... more

Madewell Shoes | Madewell Shoes Madewell Sonia Chelsea Boot Black Leather Nib | Color: Black | Size: 7

Madewell Shoes Madewell Sonia Chelsea Boot Black Leather Nib Sold Out! Retail $188

Poshmark

$115.00

go to store
Madewell Shoes | Madewell The Camryn Chelsea Boot In English Saddle Leather Cognac 8-8.5 | Color: Brown | Size: 8

Madewell Shoes | Madewell The Camryn Chelsea Boot In English Saddle Leather Cognac 8-8.5 | Color: Brown | Size: 8

Reposhing This Item I Purchased From @Kellymichael862. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! ... more

Madewell Shoes | Madewell The Camryn Chelsea Boot In English Saddle Leather Cognac 8-8.5 | Color: Brown | Size: 8

Reposhing This Item I Purchased From @Kellymichael862. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below!

Poshmark

$120.00

go to store
Madewell Shoes | Madewell The Benning Black Leather Chelsea Bootie 9 1/2 | Color: Black | Size: 9.5

Madewell Shoes | Madewell The Benning Black Leather Chelsea Bootie 9 1/2 | Color: Black | Size: 9.5

Madewell The Benning Black Leather Chelsea Booties 9 1/2 >Only Worn Once Or Twice >Style: The Benning Bootie >Chelsea, Pull On With Back Pull Tab >Round Toe, Low Stacked Heel >Color: Black, Leather >Size 9.5 >Heel Height Is Approx. 1 1/4in Please... ... more

Madewell Shoes | Madewell The Benning Black Leather Chelsea Bootie 9 1/2 | Color: Black | Size: 9.5

Madewell The Benning Black Leather Chelsea Booties 9 1/2 >Only Worn Once Or Twice >Style: The Benning Bootie >Chelsea, Pull On With Back Pull Tab >Round Toe, Low Stacked Heel >Color: Black, Leather >Size 9.5 >Heel Height Is Approx. 1 1/4in Please...

Poshmark

$90.00

go to store
Madewell Shoes | Madewell Charley Ankle Boot / Bootie Leather Suede Size 7 1/2 | Color: Brown | Size: 7.5

Madewell Shoes | Madewell Charley Ankle Boot / Bootie Leather Suede Size 7 1/2 | Color: Brown | Size: 7.5

Madewell Charley Ankle Boot / Bootie Leather Suede Size 7 1/2 Questions? Leave A Comment Below! ... more

Madewell Shoes | Madewell Charley Ankle Boot / Bootie Leather Suede Size 7 1/2 | Color: Brown | Size: 7.5

Madewell Charley Ankle Boot / Bootie Leather Suede Size 7 1/2 Questions? Leave A Comment Below!

Poshmark

$50.00

go to store