Best Seller
Madewell Shoes | Madewell Ainsley Tan Leather Chelsea Boots Ankle Booties | Color: Brown/Tan | Size: 7

Madewell Shoes | Madewell Ainsley Tan Leather Chelsea Boots Ankle Booties | Color: Brown/Tan | Size: 7

Lovely Madewell "Ainsley" Leather Chelsea Boots! Pull On Style With A Low Heel And An Almond Toe. Gently Worn And In Excellent Condition, Size 7. more

$79.00

go to store
Madewell Shoes | Madewell Leather Ankle Boots Booties Oxblood | Color: Brown/Red | Size: 7

Madewell Shoes | Madewell Leather Ankle Boots Booties Oxblood | Color: Brown/Red | Size: 7

Great Condition! Only Minor Scuffs, Please See Pics. more

$59.00

go to store
Best Seller
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

$38.00

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

$42.00

go to store
Madewell Shoes | Madewell Ankle Boots Size 8.5 Charley Brown Zip Booties Suede Leather | Color: Brown/Tan | Size: 8.5

Madewell Shoes | Madewell Ankle Boots Size 8.5 Charley Brown Zip Booties Suede Leather | Color: Brown/Tan | Size: 8.5

Madewell Ankle Boots Size 8.5 Charley Brown Zip Booties Suede Leather Size 8.5 Minor Wear On Soles, Uppers And Insoles. Good Condition, Cleaned more

$27.00

go to store
Madewell Shoes | Madewell Hailie Boot Ankle Bootie Caramel Suede Size 8 Boho Cowgirl Country Heel | Color: Brown | Size: 8

Madewell Shoes | Madewell Hailie Boot Ankle Bootie Caramel Suede Size 8 Boho Cowgirl Country Heel | Color: Brown | Size: 8

These Madewell Booties Are Definitely In Pre-Loved Condition. A Few Scuff Marks On Heels. The Finger Straps Shows Discoloration From Wear. The Toes Show Signs Of Wear. These Boots Are In Overall Good Wearing / Functioning Condition. The "Wear" Marks Do... more

$28.00

go to store
Madewell Shoes | Madewell Ankle Boots Brenner Booties Leather Classic | Color: Brown | Size: 7.5

Madewell Shoes | Madewell Ankle Boots Brenner Booties Leather Classic | Color: Brown | Size: 7.5

Madewell Brown Leather Suede Ankle Boots Booties Sz 7.5 All Leather / Soles , Inner Lining & Leather Suede Upper In Brown. Approximate 3.5” Heel Inner Zipper Closure In Overall Excellent Condition. Please Refer To Photos For Wear. No Notable Stains Or... more

$54.00

go to store
Madewell Shoes | Madewell Caleb Black Leather Block Ankle Booties Heels Zip Designer Boots 8 | Color: Black | Size: 8

Madewell Shoes | Madewell Caleb Black Leather Block Ankle Booties Heels Zip Designer Boots 8 | Color: Black | Size: 8

Madewell Caleb Black Leather Block Ankle Booties Heels Zip Designer Boots Size 8 Offers Are Always Considered. Bundle For Big Discounts. Please Do Not Hesitate To Ask If You Have Any Questions! more

$58.00

go to store
Madewell Shoes | Madewell “Grayson” Tan Suede Leather Brogue Chelsea Heeled Ankle Boots/Booties | Color: Orange/Tan | Size: 7

Madewell Shoes | Madewell “Grayson” Tan Suede Leather Brogue Chelsea Heeled Ankle Boots/Booties | Color: Orange/Tan | Size: 7

Madewell “Grayson” Tan Suede Leather Stocked Block Heel Ankle Boots/Booties. Our Design Team Took Age-Old Western Boot Details, A Stacked Raw Leather Heel, A Pointy Toe, Brogue Perforations And Cut Them Low On The Ankle To Make Your Legs Look Even... more

$69.00

go to store
Madewell Shoes | Host Pick!! Madewell Ankle Booties Leopard Print Pony Hair Tan Brown Boots | Color: Black/Tan | Size: 6

Madewell Shoes | Host Pick!! Madewell Ankle Booties Leopard Print Pony Hair Tan Brown Boots | Color: Black/Tan | Size: 6

Madewell Ankle Booties Pony Hair Leopard Animal Print / Leather Next Level Looks - Host Pick - 10/16! Size: (6) Slight Scuffing From Normal Wear - Please See Photos. Bundle & Save !! 2+ Items Added To Your Bundle Receives 10% Discount & Only One $4.99... more

$33.00

go to store
Madewell Shoes | Madewell Aimee Ankle Boots Booties Black Block 7.5 | Color: Black/Tan | Size: 7.5

Madewell Shoes | Madewell Aimee Ankle Boots Booties Black Block 7.5 | Color: Black/Tan | Size: 7.5

Madewell Womens Aimee Ankle Boots Booties Black Suede Leather Block Heel Buckle 7.5 Great Pre-Owned Condition! Slight Wear On Bottom. Discoloring On Inner Lining Near Ankles. Please See Pictures For Accurate Depiction Of Condition. Item Ships In 1... more

$45.00

go to store
Madewell Shoes | Madewell Aimee Sz 8 Booties Ankle Boots | Color: Tan | Size: 8

Madewell Shoes | Madewell Aimee Sz 8 Booties Ankle Boots | Color: Tan | Size: 8

Sz 8 Aimee From Madewell Boots, Please See Photos As Price Is Reflective Of Condition. They Are In Fair Used Condition, There Is Some Scratching In The Suede Material Mostly Around The Front Toe Area. The Straps Are Coming Apart But It's Not Noticeable... more

$20.00

go to store
Madewell Shoes | Madewell 1937 Taupe Leather Ankle Zip Booties Boots 9.5 | Color: Gray/Red/Tan | Size: 9.5

Madewell Shoes | Madewell 1937 Taupe Leather Ankle Zip Booties Boots 9.5 | Color: Gray/Red/Tan | Size: 9.5

Italian-Made Soft Taupe Leather Ankle Booties By Madewell 1937. Please Zoom In Closely On All Photos For Condition. Small Nick In The Leather Of The Inside Of Left Shoe -- Circled In Red In One Photo, And Shown Close-Up In Another Photo. Overall... more

$50.00

go to store
Madewell Shoes | Madewell Billie Boot Tan Suede Ankle Bootie 7.5 | Color: Brown/Tan | Size: 7.5

Madewell Shoes | Madewell Billie Boot Tan Suede Ankle Bootie 7.5 | Color: Brown/Tan | Size: 7.5

Madewell Super Soft Suede Leather Stacked Heel Ankle Boots In The Billie Style E0192 - Beige Tan - Stacked Heel - Zipper - Genuine Suede Upper - Leather Lining Great Pre-Owned Condition! Scuff Mark On The Outsole Rim, Minor Discoloration On The... more

$44.00

go to store
Madewell Shoes | Madewell Lace Up Ankle Booties Sz 8 Black Suede Dressy Victorian Block Heel Boot | Color: Black | Size: 8

Madewell Shoes | Madewell Lace Up Ankle Booties Sz 8 Black Suede Dressy Victorian Block Heel Boot | Color: Black | Size: 8

Madewell Amelia Women's Business Casual Boot Condition: Gently Used. Good Condition. No Flaws. Us Size: 8 (See Pictures For Measurements) Features/Accents: Ankle Style. Mid Block Heel. Round Toe. Black Color. Lace Up Closure. Material: Suede Upper,... more

$60.00

go to store
Madewell Shoes | Madewell Asher Ankle Booties Black Suede Leather Zippered Boot Size 7 | Color: Black | Size: 7

Madewell Shoes | Madewell Asher Ankle Booties Black Suede Leather Zippered Boot Size 7 | Color: Black | Size: 7

Almond Toe Ankle Booties From Madewell. Black Suede With Contrast Leather Heel. Features Zippered Entry, Block Heel & Classic Silhouette Perfect With Jeans, Leggings, Dresses & Skirts! Preloved Condition With Wear At Heel As Shown, Otherwise No Holes... more

$50.00

go to store
Madewell Shoes | Madewell Sonia Chelsea Ankle Bootie Boot Snakeskin 6 | Color: Brown | Size: 6

Madewell Shoes | Madewell Sonia Chelsea Ankle Bootie Boot Snakeskin 6 | Color: Brown | Size: 6

Madewell Sonia Chelsea Boot Color: Brown Snakeskin Size 6 Style #M3463 Retail $188 New W/O Box An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. Pull-On Style With... more

$50.00

go to store
Madewell Shoes | Madewell Pauline Taupe Tan Suede Ankle Boots Booties Shoes | Color: Tan | Size: 7.5

Madewell Shoes | Madewell Pauline Taupe Tan Suede Ankle Boots Booties Shoes | Color: Tan | Size: 7.5

Here Is A Pair Of Madewell Pauline Women's Taupe Tan Suede Ankle Boots Booties Shoes Size 7.5. They Are In Good Condition With The Exception Some Wear, A Little Wear As Shown In The Pictures, And A Spot Or Two, But Has Lots Of Life Left. The Heel... more

$50.00

go to store
Madewell Shoes | Madewell The Brady Lowcut Bootie Saddle Tan Brown Leather Ankle Boho Boots - 8 | Color: Brown/Tan | Size: 8

Madewell Shoes | Madewell The Brady Lowcut Bootie Saddle Tan Brown Leather Ankle Boho Boots - 8 | Color: Brown/Tan | Size: 8

Madewell The Brady Lowcut Bootie In Saddle Brown Leather. Great Pre-Owned Condition! Leather Has Some Creasing On The Front. Soles Have Minor Wear. Size 8. 2 Inch Heel. more

$38.00

go to store
Madewell Shoes | Madewell Rosie Snakeskin Ankle Boots Booties | Color: Brown/Tan | Size: 9

Madewell Shoes | Madewell Rosie Snakeskin Ankle Boots Booties | Color: Brown/Tan | Size: 9

Reposhing This Item I Purchased From @Voyageisaverb. Adorable, But I Have To Stick To Flats. more

$60.00

go to store
Madewell Shoes | Madewell Barnwood Suede Ankle Booties Sz 6.5 Boots | Color: Brown/Green | Size: 6.5

Madewell Shoes | Madewell Barnwood Suede Ankle Booties Sz 6.5 Boots | Color: Brown/Green | Size: 6.5

Excellent Pair Of Madewell Barnwood Suede Ankle Boots In Overall Great Condition. Worn Only A Couple Times. Only Flaws Are A Couple Scuffs On Heel Edge And Suede Upper. Color Is Mink (A Cross Between Brown And Olive Green) Size 6 1/2. “A... more

$47.00

go to store
Madewell Shoes | Madewell Grayson Chelsea Velvet Ankle Boots / Booties / Shooties Size 9 Country | Color: Silver | Size: 9

Madewell Shoes | Madewell Grayson Chelsea Velvet Ankle Boots / Booties / Shooties Size 9 Country | Color: Silver | Size: 9

Madewell Genuine Leather Grayson Chelsea Velvet Ankle Boots Size 9, Small Spots Hardly Noticeable See Picture 9, Otherwise These Boots Are In Excellent Used Condition. more

$30.00

go to store
Madewell Shoes | Madewell | Tan Leather Ankle Boots Heel Booties | Color: Brown/Tan | Size: 8.5

Madewell Shoes | Madewell | Tan Leather Ankle Boots Heel Booties | Color: Brown/Tan | Size: 8.5

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

$68.00

go to store
Madewell Shoes | Madewell Janice Ankle Boot Bootie Brown F5076 | Color: Brown | Size: 7

Madewell Shoes | Madewell Janice Ankle Boot Bootie Brown F5076 | Color: Brown | Size: 7

- Trendy - Chic - Casual Questions? Leave A Comment Below! 0154 more

$28.00

go to store
Madewell Shoes | Madewell Tan Suede Leather Ankle Boot Booties Bloc | Color: Tan | Size: 7

Madewell Shoes | Madewell Tan Suede Leather Ankle Boot Booties Bloc | Color: Tan | Size: 7

Madewell Tan Suede Leather Block Heel Ankle Boot Booties. Slightly Rounded Square Toe. Size 7. Very Good Pre-Owned Condition As Pictured. more

$32.00

go to store
Madewell Shoes | Madewell The Barnwood Boots 1937 Genuine Leather Suede Black Ankle Booties S 6 | Color: Black | Size: 6

Madewell Shoes | Madewell The Barnwood Boots 1937 Genuine Leather Suede Black Ankle Booties S 6 | Color: Black | Size: 6

Madewell The Barnwood Boots 1937 Genuine Leather Suede Black Ankle Booties S 6 Good Preowned Condition, Slight Scuffing On Leather, See Photos Offers Welcome! Genuine Leather Suede, Elevated Basic, Closet Staple, Boho, Bohemian, Indie Sleaze, Western,... more

$45.00

go to store
Madewell Shoes | Madewell The Regan Boots Ankle Booties Beige Suede Block Heels | Color: Tan | Size: 9

Madewell Shoes | Madewell The Regan Boots Ankle Booties Beige Suede Block Heels | Color: Tan | Size: 9

Preowned Some Marks And Color Transfer Please See Pictures For Details Size 9 more

$55.00

go to store
Madewell Shoes | Madewell The Lonnie Boot Khaki Brown Suede Leather Ankle Bootie | Color: Brown | Size: 9

Madewell Shoes | Madewell The Lonnie Boot Khaki Brown Suede Leather Ankle Bootie | Color: Brown | Size: 9

Madewell The Lonnie Boot Khaki Brown Suede Leather Ankle Bootie Size Women's 9 Used /See Photos more

$35.00

go to store
Madewell Shoes | Madewell Et Sezane High Heel Tassel Black Leather Ankle Boots Booties Size 8 | Color: Black | Size: 8

Madewell Shoes | Madewell Et Sezane High Heel Tassel Black Leather Ankle Boots Booties Size 8 | Color: Black | Size: 8

Pre Own In Good Condition Size 8m more

$13.00

go to store
Madewell Shoes | Madewell Otis Tan Brown Leather Pull-On Chelsea Ankle Booties Boots | Color: Tan | Size: 6.5

Madewell Shoes | Madewell Otis Tan Brown Leather Pull-On Chelsea Ankle Booties Boots | Color: Tan | Size: 6.5

Previously Loved In Good Condition, Some Wear On The Upper And Soles With Lots Of Life Left; Small Tear On Leather Lining Of Inside Left Boot. Tan Leather Colorway, Women’s Size 6.5 Refer To Pictures And Reach Out With Any Questions Bundle Items To... more

$49.00

go to store
Madewell Shoes | Madewell Leather Ankle Boots 1937 Footwear Short Heeled Booties | Color: Brown/Tan | Size: 6.5

Madewell Shoes | Madewell Leather Ankle Boots 1937 Footwear Short Heeled Booties | Color: Brown/Tan | Size: 6.5

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

$15.00

go to store
Madewell Shoes | Madewell The Billie Leather Ankle Boot Booties Brown 7.5 | Color: Brown | Size: 7.5

Madewell Shoes | Madewell The Billie Leather Ankle Boot Booties Brown 7.5 | Color: Brown | Size: 7.5

Brand - Madewell Size - 7.5 Excellent Preowned Condition Western, Bootie, Ankle, Short, Leather, Side Zipper, Stacked Block Heel, Brown, Tan, Round Almond Toe more

$40.00

go to store
Madewell Shoes | Madewell Billie Boot - 7.5 Black Leather Ankle Bootie | Color: Black | Size: 7.5

Madewell Shoes | Madewell Billie Boot - 7.5 Black Leather Ankle Bootie | Color: Black | Size: 7.5

Well Loved 7.5 Black Leather Booties "The Billie Boot" From Madewell. Extremely Comfortable And Go With Everything!! Minor Wear And Tear On Block Heel As Pictured. more

$32.00

go to store
Madewell Shoes | Madewell Pull On Ankle Boot Size 9.5 Regan Black Leather Chelsea J8307 Booties | Color: Black | Size: 9.5

Madewell Shoes | Madewell Pull On Ankle Boot Size 9.5 Regan Black Leather Chelsea J8307 Booties | Color: Black | Size: 9.5

Madewell Pull On Ankle Boot Size 9.5 Regan Black Leather Chelsea J8307 Booties Excellent Preowned Condition. Madewell Regan Size 9.5 Black Leather Upper And Lining Stacked Heel 2.5 " Heel Cloudlift Lite Padding Retails For $178 Style J8307 Hard To... more

$71.00

go to store
Madewell Shoes | Madewell Billie Tan Suede Leather Ankle Booties/Boots Size 8 | Color: Tan | Size: 9

Madewell Shoes | Madewell Billie Tan Suede Leather Ankle Booties/Boots Size 8 | Color: Tan | Size: 9

The Actual Color Is Tan Excellent Condition (No Rips, Tears, Stains, Fabric Shows No / Minimal Signs Of Wear). See Pics For Details Lower-On-The-Ankle Cut (Same Rich Suede, Walkable Stacked Heel And Wear-With-Everything Silhouette). Also New? The... more

$55.00

go to store
Madewell Shoes | Madewell - Nico, Black Ankle Boots Booties 8.5 | Color: Black | Size: 8.5

Madewell Shoes | Madewell - Nico, Black Ankle Boots Booties 8.5 | Color: Black | Size: 8.5

In Great Pre-Owned Condition. 8.5 Made In Brazil Smooth Black Leather With A Pointed Toe. Slip On Style. more

$50.00

go to store
Madewell Shoes | Madewell $228 The Pauline Boot In Suede Ankle Booties Size 7.5m Back Zipper | Color: Gray/Tan | Size: 7.5

Madewell Shoes | Madewell $228 The Pauline Boot In Suede Ankle Booties Size 7.5m Back Zipper | Color: Gray/Tan | Size: 7.5

A Wear-Everywhere Ankle Boot Made Of Buttery Suede With Easy-To-Break-In Leather Soles. This Sleek Design Is Cut At Just The Right Height On The Leg To Pair With Cropped Denim. 2 1/4" Heel. Suede Upper. Leather Lining And Sole. Back Zipper Closure... more

$56.00

go to store
Madewell Shoes | Madewell Brown Suede & Leather Side Zip Cait Ankle Boot Booties Size 7.5 | Color: Brown/Tan | Size: 7.5

Madewell Shoes | Madewell Brown Suede & Leather Side Zip Cait Ankle Boot Booties Size 7.5 | Color: Brown/Tan | Size: 7.5

Madewell Brown Suede & Leather Side Zip Cait Ankle Boot Booties Brand: Madewell Size: 7.5 Color: Brown Style: Cait Suede Front, Leather Back Side Zip Low Stacked Heel Measurements: Boot Height: 5.5" Condition: Pre-Owned Condition Please See Images For... more

$48.00

go to store
Madewell Shoes | Madewell Tan Leather Booties Ankle Boots | Color: Tan | Size: 8.5

Madewell Shoes | Madewell Tan Leather Booties Ankle Boots | Color: Tan | Size: 8.5

Madewell Leather Booties Women’s Size 8.5 Tan Leather Doesn’t Come With Shoe Box Has Scratches Around Toes All Wear Shown In Pictures more

$40.00

go to store
Madewell Shoes | Madewell The Cait Ankle Boots Leather Tan/Brown Suede Booties Color Block 7.5 | Color: Tan | Size: 7.5

Madewell Shoes | Madewell The Cait Ankle Boots Leather Tan/Brown Suede Booties Color Block 7.5 | Color: Tan | Size: 7.5

Madewell The Cait Ankle Boots Leather Tan/Brown Suede Booties Color Block 7.5 Heel Is Aprox 2” Height more

$66.00

go to store

More information about Men's Shoes

Best prices on Madewell ankle boots booties chunky in Men's Shoes online. Visit Bizrate to find the best deals on top brands. Read reviews on Clothing & Accessories merchants and buy with confidence.