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 TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EEEE)

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EEEE)

Drew Trevino are casual, yet comfortable ankle boots that combine 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. Drew... ... more

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EEEE)

Drew Trevino are casual, yet comfortable ankle boots that combine 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. Drew...

KingSize Direct

$220.99

go to store
Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 D)

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 D)

Drew Trevino are casual, yet comfortable ankle boots that combine 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. Drew... ... more

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 D)

Drew Trevino are casual, yet comfortable ankle boots that combine 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. Drew...

KingSize Direct

$220.99

go to store
Best Seller
Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 EE)

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 EE)

Drew Trevino are casual, yet comfortable ankle boots that combine 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. Drew... ... more

Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 EE)

Drew Trevino are casual, yet comfortable ankle boots that combine 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. Drew...

KingSize Direct

$220.99

go to store
Madewell Shoes | Madewell Camryn Tan Brown Chelsea Boot Bootie Size 8 - Never Worn | Color: Brown/Tan | Size: 8

Madewell Shoes | Madewell Camryn Tan Brown Chelsea Boot Bootie Size 8 - Never Worn | Color: Brown/Tan | Size: 8

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 Taking These On And Off A Breeze And, Cushiness Alert, Our Mwl... ... more

Madewell Shoes | Madewell Camryn Tan Brown Chelsea Boot Bootie Size 8 - Never Worn | Color: Brown/Tan | Size: 8

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 Taking These On And Off A Breeze And, Cushiness Alert, Our Mwl...

Poshmark

$100.00

go to store
Madewell Shoes | **Brand New** Madewell Leather Tall Cognac Brown Boots. Size 6.5. Never Worn. | Color: Brown | Size: 6.5

Madewell Shoes | **Brand New** Madewell Leather Tall Cognac Brown Boots. Size 6.5. Never Worn. | Color: Brown | Size: 6.5

Brand New, Never Worn Perfect Condition Madewell Boots. 100% Leather! Purchased A Size Too Small! ... more

Madewell Shoes | **Brand New** Madewell Leather Tall Cognac Brown Boots. Size 6.5. Never Worn. | Color: Brown | Size: 6.5

Brand New, Never Worn Perfect Condition Madewell Boots. 100% Leather! Purchased A Size Too Small!

Poshmark

$125.00

go to store
Men's Park Drew Shoe by Drew in Brown Leather (Size 11 1/2 M)

Men's Park Drew Shoe by Drew in Brown Leather (Size 11 1/2 M)

The Park men's dress shoe by Drew® is a favorite for guys who want a stylish casual shoe with the therapeutic benefits of a Drew. With its sleek, classic design, you'd never know it's therapeutically beneficial! Added depth, extended heel counter and... ... more

Men's Park Drew Shoe by Drew in Brown Leather (Size 11 1/2 M)

The Park men's dress shoe by Drew® is a favorite for guys who want a stylish casual shoe with the therapeutic benefits of a Drew. With its sleek, classic design, you'd never know it's therapeutically beneficial! Added depth, extended heel counter and...

KingSize Direct

$239.99

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 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 Park Drew Shoe by Drew in Brown Leather (Size 9 W)

Wide Width Men's Park Drew Shoe by Drew in Brown Leather (Size 9 W)

The Park men's dress shoe by Drew® is a favorite for guys who want a stylish casual shoe with the therapeutic benefits of a Drew. With its sleek, classic design, you'd never know it's therapeutically beneficial! Added depth, extended heel counter and... ... more

Wide Width Men's Park Drew Shoe by Drew in Brown Leather (Size 9 W)

The Park men's dress shoe by Drew® is a favorite for guys who want a stylish casual shoe with the therapeutic benefits of a Drew. With its sleek, classic design, you'd never know it's therapeutically beneficial! Added depth, extended heel counter and...

KingSize Direct

$246.99

go to store
Wide Width Men's Park Drew Shoe by Drew in Brown Leather (Size 9 1/2 W)

Wide Width Men's Park Drew Shoe by Drew in Brown Leather (Size 9 1/2 W)

The Park men's dress shoe by Drew® is a favorite for guys who want a stylish casual shoe with the therapeutic benefits of a Drew. With its sleek, classic design, you'd never know it's therapeutically beneficial! Added depth, extended heel counter and... ... more

Wide Width Men's Park Drew Shoe by Drew in Brown Leather (Size 9 1/2 W)

The Park men's dress shoe by Drew® is a favorite for guys who want a stylish casual shoe with the therapeutic benefits of a Drew. With its sleek, classic design, you'd never know it's therapeutically beneficial! Added depth, extended heel counter and...

KingSize Direct

$246.99

go to store
Men's Park Drew Shoe by Drew in Brown Leather (Size 9 M)

Men's Park Drew Shoe by Drew in Brown Leather (Size 9 M)

The Park men's dress shoe by Drew® is a favorite for guys who want a stylish casual shoe with the therapeutic benefits of a Drew. With its sleek, classic design, you'd never know it's therapeutically beneficial! Added depth, extended heel counter and... ... more

Men's Park Drew Shoe by Drew in Brown Leather (Size 9 M)

The Park men's dress shoe by Drew® is a favorite for guys who want a stylish casual shoe with the therapeutic benefits of a Drew. With its sleek, classic design, you'd never know it's therapeutically beneficial! Added depth, extended heel counter and...

KingSize Direct

$239.99

go to store
Madewell Shoes | Brown Leather Madewell Sandals Size 7.5 Never Worn | Color: Brown | Size: 7.5

Madewell Shoes | Brown Leather Madewell Sandals Size 7.5 Never Worn | Color: Brown | Size: 7.5

Brown Leather Madewell Sandals Size 7.5 Never Worn ... more

$32.00

go to store
Madewell Shoes | Brand New Madewell Boots. Never Worn. | Color: Brown | Size: 7

Madewell Shoes | Brand New Madewell Boots. Never Worn. | Color: Brown | Size: 7

I Bought These Because I Loved The Color But Personally Find Them A Little Pointier Than I Would Like. Brand New, Never Worn, Comes With Original Madewell Box. Size 7. ... more

Madewell Shoes | Brand New Madewell Boots. Never Worn. | Color: Brown | Size: 7

I Bought These Because I Loved The Color But Personally Find Them A Little Pointier Than I Would Like. Brand New, Never Worn, Comes With Original Madewell Box. Size 7.

Poshmark

$89.00

go to store
Madewell Shoes | Madewell Ainsley Brown Leather Chelsea Ankle Boots Size 6.5 | Color: Brown | Size: 6.5

Madewell Shoes | Madewell Ainsley Brown Leather Chelsea Ankle Boots Size 6.5 | Color: Brown | Size: 6.5

Madewell Ainsley Brown Leather Chelsea Ankle Boots Size 6.5 Gently Used, Signs Of Wear Are On The Sole. Leather Is In Great Condition. ... more

Madewell Shoes | Madewell Ainsley Brown Leather Chelsea Ankle Boots Size 6.5 | Color: Brown | Size: 6.5

Madewell Ainsley Brown Leather Chelsea Ankle Boots Size 6.5 Gently Used, Signs Of Wear Are On The Sole. Leather Is In Great Condition.

Poshmark

$65.00

go to store
Madewell Shoes | Madewell Laura Chelsea Heeled Brown Leather Boot | Size 9.5 | Color: Brown | Size: 9.5

Madewell Shoes | Madewell Laura Chelsea Heeled Brown Leather Boot | Size 9.5 | Color: Brown | Size: 9.5

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

Madewell Shoes | Madewell Laura Chelsea Heeled Brown Leather Boot | Size 9.5 | Color: Brown | Size: 9.5

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

Poshmark

$70.00

go to store
Madewell Shoes | New Madewell Brown Regan Snake Embossed Chelsea Leather Ankle Boots Size 5.5m | Color: Black/Brown | Size: 5.5

Madewell Shoes | New Madewell Brown Regan Snake Embossed Chelsea Leather Ankle Boots Size 5.5m | Color: Black/Brown | Size: 5.5

Gorgeous Pair Of Regan Snake Embossed Leather Chelsea Booties With 2.5" Stacked Heels By Madewell. Color Is Called Warm Ash Multi. Us Size 5.5 M. New Without The Box. Original Retail Price $198. Smoke Free Home. ... more

Madewell Shoes | New Madewell Brown Regan Snake Embossed Chelsea Leather Ankle Boots Size 5.5m | Color: Black/Brown | Size: 5.5

Gorgeous Pair Of Regan Snake Embossed Leather Chelsea Booties With 2.5" Stacked Heels By Madewell. Color Is Called Warm Ash Multi. Us Size 5.5 M. New Without The Box. Original Retail Price $198. Smoke Free Home.

Poshmark

$89.00

go to store
Madewell Shoes | Madewell Ivy Chelsea Boot Croc Embossed Leather Size 6 Brown | Color: Brown | Size: 6

Madewell Shoes | Madewell Ivy Chelsea Boot Croc Embossed Leather Size 6 Brown | Color: Brown | Size: 6

Madewell Ivy Chelsea Boot Croc Embossed Leather Size 6 Brown. Some Signs Of Wear ... more

Madewell Shoes | Madewell Ivy Chelsea Boot Croc Embossed Leather Size 6 Brown | Color: Brown | Size: 6

Madewell Ivy Chelsea Boot Croc Embossed Leather Size 6 Brown. Some Signs Of Wear

Poshmark

$40.00

go to store
Madewell Shoes | Madewell The Kelci Chelsea Boot Size 7 Cognac Brown Leather Heeled Ankle Booties | Color: Brown | Size: 7

Madewell Shoes | Madewell The Kelci Chelsea Boot Size 7 Cognac Brown Leather Heeled Ankle Booties | Color: Brown | Size: 7

Madewell The Kelci Chelsea Boot Size 7 Cognac Brown Leather Heeled Ankle Booties Great Preowned Condition With No Flaws And Minor Wear To The Leather And Soles - See All Photos For Best Description Stacked Heel - Pointy Toe - Cut Low On The Ankle -... ... more

Madewell Shoes | Madewell The Kelci Chelsea Boot Size 7 Cognac Brown Leather Heeled Ankle Booties | Color: Brown | Size: 7

Madewell The Kelci Chelsea Boot Size 7 Cognac Brown Leather Heeled Ankle Booties Great Preowned Condition With No Flaws And Minor Wear To The Leather And Soles - See All Photos For Best Description Stacked Heel - Pointy Toe - Cut Low On The Ankle -...

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
Madewell Shoes | Madewell Grayson Brogue Suede Leather Western Chelsea Boot Size 7.5 Bootie Brown | Color: Brown/Tan | Size: 7.5

Madewell Shoes | Madewell Grayson Brogue Suede Leather Western Chelsea Boot Size 7.5 Bootie Brown | Color: Brown/Tan | Size: 7.5

Madewell Grayson Brogue Suede Leather Western Chelsea Boot Size 7.5 Bootie Brown Excellent Condition Size 7.5 Features: Slip On, Amber Brown, Pointed Toe, Low Heel, Boot, Bootie Bundle This Item With One Or More Items From My Closet To Receive A... ... more

Madewell Shoes | Madewell Grayson Brogue Suede Leather Western Chelsea Boot Size 7.5 Bootie Brown | Color: Brown/Tan | Size: 7.5

Madewell Grayson Brogue Suede Leather Western Chelsea Boot Size 7.5 Bootie Brown Excellent Condition Size 7.5 Features: Slip On, Amber Brown, Pointed Toe, Low Heel, Boot, Bootie Bundle This Item With One Or More Items From My Closet To Receive A...

Poshmark

$65.00

go to store
Madewell Shoes | Madewell Ivy Chelsea Boot In Croc Embossed Leather, Size 9, Dark Coffee Color | Color: Brown | Size: 9

Madewell Shoes | Madewell Ivy Chelsea Boot In Croc Embossed Leather, Size 9, Dark Coffee Color | Color: Brown | Size: 9

Great Condition, Only Worn Inside To Try On ... more

$50.00

go to store
Madewell Shoes | Madewell Brown Leather Chelsea Boots | Color: Brown/Tan | Size: 6

Madewell Shoes | Madewell Brown Leather Chelsea Boots | Color: Brown/Tan | Size: 6

Lightly Worn Madewell Chelsea Boots In Copper Leather. Short Heel, Structured Leather. ... more

Madewell Shoes | Madewell Brown Leather Chelsea Boots | Color: Brown/Tan | Size: 6

Lightly Worn Madewell Chelsea Boots In Copper Leather. Short Heel, Structured Leather.

Poshmark

$65.00

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 Ivy Chelsea Boot Brown Embossed Leather Croc | Color: Black/Brown | Size: 7

Madewell Shoes | Madewell Ivy Chelsea Boot Brown Embossed Leather Croc | Color: Black/Brown | Size: 7

These Were Only Worn Once! They’re In Excellent Condition. They’re A Classic Chelsea Boot With A Utilitarian Lug Sole With Black And Tan Layers. They Have The Mwl Cloudlift Lite Padding That Feels Like Walking On A Cloud! 5 1/4 Inch Shaft 3/4 Inch Heel ... more

Madewell Shoes | Madewell Ivy Chelsea Boot Brown Embossed Leather Croc | Color: Black/Brown | Size: 7

These Were Only Worn Once! They’re In Excellent Condition. They’re A Classic Chelsea Boot With A Utilitarian Lug Sole With Black And Tan Layers. They Have The Mwl Cloudlift Lite Padding That Feels Like Walking On A Cloud! 5 1/4 Inch Shaft 3/4 Inch Heel

Poshmark

$70.00

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 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 Brown Leather Chelsea Boots | Color: Brown | Size: 7.5

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

Madewell Brown Leather Chelsea Boots ... more

$50.00

go to store
Madewell Shoes | Madewell The Benning Chelsea Brown Leather Boot | Color: Brown | Size: 6

Madewell Shoes | Madewell The Benning Chelsea Brown Leather Boot | Color: Brown | Size: 6

Brown Super-Soft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. 5 1/4" Shaft Height. Leather Upper. Leather Lining. Man-Made Sole. ... more

Madewell Shoes | Madewell The Benning Chelsea Brown Leather Boot | Color: Brown | Size: 6

Brown Super-Soft Leather, These Chelsea Boot Have Stretchy Gores And A Walkable Stacked Heel. Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. 5 1/4" Shaft Height. Leather Upper. Leather Lining. Man-Made Sole.

Poshmark

$85.00

go to store
Madewell Shoes | Madewell - Cleary Chelsea Boot In Leather - Nh206 - Size 8 | Color: Brown/Orange | Size: 8

Madewell Shoes | Madewell - Cleary Chelsea Boot In Leather - Nh206 - Size 8 | Color: Brown/Orange | Size: 8

Reposhing This Item I Purchased From @_seek_and_find_. These Were Too Tight On Me. Apparently I Have Much More Wide Feet Postpartum! They’re In Great Condition. Never Worn By Me Only To Try Them On In The House. Genuine Leather English Saddle Color ... more

Madewell Shoes | Madewell - Cleary Chelsea Boot In Leather - Nh206 - Size 8 | Color: Brown/Orange | Size: 8

Reposhing This Item I Purchased From @_seek_and_find_. These Were Too Tight On Me. Apparently I Have Much More Wide Feet Postpartum! They’re In Great Condition. Never Worn By Me Only To Try Them On In The House. Genuine Leather English Saddle Color

Poshmark

$60.00

go to store
Madewell Shoes | Madewell Chelsea Boot Crocodile Leather Size 10 | Color: Brown | Size: 10

Madewell Shoes | Madewell Chelsea Boot Crocodile Leather Size 10 | Color: Brown | Size: 10

Great Condition - Only Worn A Couple Times! Size 10 Brown Crocodile Leather ... more

Madewell Shoes | Madewell Chelsea Boot Crocodile Leather Size 10 | Color: Brown | Size: 10

Great Condition - Only Worn A Couple Times! Size 10 Brown Crocodile Leather

Poshmark

$99.00

go to store
Madewell Shoes | New Madewell Leather Chelsea Boots | Color: Brown | Size: 7

Madewell Shoes | New Madewell Leather Chelsea Boots | Color: Brown | Size: 7

New Without Tags, Never Worn Outside. Beautiful, In Perfect Condition. ... more

Madewell Shoes | New Madewell Leather Chelsea Boots | Color: Brown | Size: 7

New Without Tags, Never Worn Outside. Beautiful, In Perfect Condition.

Poshmark

$45.00

go to store
Madewell Shoes | Madewell Regan Chelsea Boot Cognac Leather Size 9.5 | Color: Brown | Size: 9.5

Madewell Shoes | Madewell Regan Chelsea Boot Cognac Leather Size 9.5 | Color: Brown | Size: 9.5

Sold Out Online. Barely Worn, One Small Scuff On Heel (Pictured). From Madewell: Made Of Rich Leather, These Cool Pull-On Boots Have Block Heels For A Little Extra Height. Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well,... ... more

Madewell Shoes | Madewell Regan Chelsea Boot Cognac Leather Size 9.5 | Color: Brown | Size: 9.5

Sold Out Online. Barely Worn, One Small Scuff On Heel (Pictured). From Madewell: Made Of Rich Leather, These Cool Pull-On Boots Have Block Heels For A Little Extra Height. Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well,...

Poshmark

$125.00

go to store
Madewell Shoes | Madewell The Clearly Chelsea Boot In Leather | Color: Brown/Tan | Size: 7.5

Madewell Shoes | Madewell The Clearly Chelsea Boot In Leather | Color: Brown/Tan | Size: 7.5

Size 7.5 In Color English Saddle! Brand New In Box Never Worn! ... more

$125.00

go to store
Madewell Shoes | Madewell Grayson Brogue Chelsea Ankle Boot Western Suede 8.5 Brown Wingtip Boots | Color: Brown | Size: 8.5

Madewell Shoes | Madewell Grayson Brogue Chelsea Ankle Boot Western Suede 8.5 Brown Wingtip Boots | Color: Brown | Size: 8.5

Brownish Burnt Orangy Color Wingtip Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toe, Brogue Perforationsand Cut Them Low On The Ankle To Make Your Legs Look Even Longer. A Pull-On Style For In-Between Weather... ... more

Madewell Shoes | Madewell Grayson Brogue Chelsea Ankle Boot Western Suede 8.5 Brown Wingtip Boots | Color: Brown | Size: 8.5

Brownish Burnt Orangy Color Wingtip Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toe, Brogue Perforationsand Cut Them Low On The Ankle To Make Your Legs Look Even Longer. A Pull-On Style For In-Between Weather...

Poshmark

$60.00

go to store
Madewell Shoes | New Madewell Bradley Chelsea Brown Boots Size 7 1/2 | Color: Brown | Size: 7.5

Madewell Shoes | New Madewell Bradley Chelsea Brown Boots Size 7 1/2 | Color: Brown | Size: 7.5

New And Never Worn Size 7 1/2. Description From Website Hit The Streets In This Classic Pull-On Chelsea Boot With Superchunky Lug Soles. The Wide Elastic Gore Not Only Looks Cool, But Also Makes On-And-Offs So Easy. And, Cushiness Alert: Our Mwl... ... more

Madewell Shoes | New Madewell Bradley Chelsea Brown Boots Size 7 1/2 | Color: Brown | Size: 7.5

New And Never Worn Size 7 1/2. Description From Website Hit The Streets In This Classic Pull-On Chelsea Boot With Superchunky Lug Soles. The Wide Elastic Gore Not Only Looks Cool, But Also Makes On-And-Offs So Easy. And, Cushiness Alert: Our Mwl...

Poshmark

$80.00

go to store
Madewell Shoes | Madewell Carina Snake Embossed Leather Chelsea Ankle Boots Womens Size 7 New | Color: Brown/Cream | Size: 7

Madewell Shoes | Madewell Carina Snake Embossed Leather Chelsea Ankle Boots Womens Size 7 New | Color: Brown/Cream | Size: 7

Madewell Carina Snake Embossed Leather Chelsea Ankle Boots Womens Size 7 New Without Box Snake Print ... more

Madewell Shoes | Madewell Carina Snake Embossed Leather Chelsea Ankle Boots Womens Size 7 New | Color: Brown/Cream | Size: 7

Madewell Carina Snake Embossed Leather Chelsea Ankle Boots Womens Size 7 New Without Box Snake Print

Poshmark

$45.00

go to store
Madewell Shoes | Madewell Reagan Snakeskin Printed Leather Heeled Chelsea Boots Size 7 | Color: Black/Brown | Size: 7

Madewell Shoes | Madewell Reagan Snakeskin Printed Leather Heeled Chelsea Boots Size 7 | Color: Black/Brown | Size: 7

Leather Textured Printed Upper, Man Made Lower. 2.5” Heel, Small Scratch On Heel As Pictured. Wore Them With Dresses And Got Lots Of Compliments. ... more

Madewell Shoes | Madewell Reagan Snakeskin Printed Leather Heeled Chelsea Boots Size 7 | Color: Black/Brown | Size: 7

Leather Textured Printed Upper, Man Made Lower. 2.5” Heel, Small Scratch On Heel As Pictured. Wore Them With Dresses And Got Lots Of Compliments.

Poshmark

$30.00

go to store
Madewell Shoes | Madewell Platform Chelsea Boots- Leather And Suede | Color: Brown | Size: 9

Madewell Shoes | Madewell Platform Chelsea Boots- Leather And Suede | Color: Brown | Size: 9

Like New! Only Worn A Few Times. Just Can’t Pull These Off! Super High Quality. ... more

Madewell Shoes | Madewell Platform Chelsea Boots- Leather And Suede | Color: Brown | Size: 9

Like New! Only Worn A Few Times. Just Can’t Pull These Off! Super High Quality.

Poshmark

$110.00

go to store
Madewell Shoes | Madewell Chelsea Leather Boot | Color: Brown | Size: 9.5

Madewell Shoes | Madewell Chelsea Leather Boot | Color: Brown | Size: 9.5

Gently Worn Madewell Regan Leather Pull On Boots. Cognac Brown Leather With Mid-Size Block Heel. ... more

Madewell Shoes | Madewell Chelsea Leather Boot | Color: Brown | Size: 9.5

Gently Worn Madewell Regan Leather Pull On Boots. Cognac Brown Leather With Mid-Size Block Heel.

Poshmark

$99.00

go to store