Best Seller
Madewell Shoes | Madewell Rosie Leather Ankle Boot | Color: Brown/Tan | Size: 6.5

Madewell Shoes | Madewell Rosie Leather Ankle Boot | Color: Brown/Tan | Size: 6.5

Never Worn. Rich Tan Leather, With A Stacked Heel, Madewell Cloudlift Lite Padding Insole. 4" Shaft Height, 2 1/2" Heel. Leather Upper And Lining, Man-Made Sole. Two Small Scuffs , Sticker Residue On Insoles. more

$65.00

go to store
Madewell Shoes | Madewell Skylar Fringe Suede Ankle Boot, Size 8 Euc | Color: Brown | Size: 8

Madewell Shoes | Madewell Skylar Fringe Suede Ankle Boot, Size 8 Euc | Color: Brown | Size: 8

Perfect Boot For The Fall. Feature Fringe Detail Running Down Exterior Side Of Each Boot And Concealed Interior Size Zip. Boots Are In Excellent Used Condition And Come From Smoke-Free, Pet-Free Home. See Photos For Additional Details. Made In Brazil. more

$78.00

go to store
Best Seller
Madewell Shoes | Madewell The Watkin Ankle Boot In Toffee | Color: Brown/Tan | Size: 8

Madewell Shoes | Madewell The Watkin Ankle Boot In Toffee | Color: Brown/Tan | Size: 8

Madewell The Watkin Ankle Boot In Toffee Suede Size 8 Like New, Small Mark To Suede Features: Western, Stylish, Suede, Neutral, Madewell, Winter, Fall, Fall Fashion, Trendy, Booties, Boots, Low Heel, Ankle Boot Size: Womens 8 more

$100.00

go to store
Madewell Shoes | Madewell The Mira Side-Seam Ankle Boots Suede Woman’s Size 9.5 | Color: Brown/Tan | Size: 9.5

Madewell Shoes | Madewell The Mira Side-Seam Ankle Boots Suede Woman’s Size 9.5 | Color: Brown/Tan | Size: 9.5

Madewell The Mira Side-Seam Ankle Boots Suede Woman’s Size 9.5 Brand- Madewell Style #- 202 Size- 9.5 Material- Suede Outside W/ Leather On Inside Color- Tan W/ Brown Bottoms Condition-Good Condition Original $198 more

$37.00

go to store
Madewell Shoes | Madewell The Evelyn Lace-Up Ankle Boot In Dried Maple | Color: Brown | Size: 9.5

Madewell Shoes | Madewell The Evelyn Lace-Up Ankle Boot In Dried Maple | Color: Brown | Size: 9.5

Madewell The Evelyn Lace-Up Ankle Boot In Dried Maple Brown Leather Size 9.5 In Good Condition, Some Scratches To The Leather Features: Hiking Boots, Lace-Up, Combat, Stylish, Leather, Neutral, Madewell, Winter, Fall, Fall Fashion, Trendy, Booties,... more

$75.00

go to store
Madewell Shoes | Madewell Snakeskin Ankle Boots | Color: Brown/Tan | Size: 9.5

Madewell Shoes | Madewell Snakeskin Ankle Boots | Color: Brown/Tan | Size: 9.5

The Gloria Shoe Boot In Snake Embossed Leather. They Look So Good On!! Sold Out On The Madewell Website. (I’m Glad They’re Not My Size Because If They Were, I’d Probably Be Tempted To Keep Them.) more

$28.00

go to store
Madewell Shoes | Madewell Mira Side-Seam Ankle Boot In English Saddle Leather - Size 5 | Color: Brown | Size: 5

Madewell Shoes | Madewell Mira Side-Seam Ankle Boot In English Saddle Leather - Size 5 | Color: Brown | Size: 5

Minor Scuffs On Toe Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know. 2 1/2" Heel. Leather Upper. more

$98.00

go to store
Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot Suede Ankle Booties Western Oxford 8 | Color: Brown | Size: 8

Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot Suede Ankle Booties Western Oxford 8 | Color: Brown | Size: 8

Madewell The Grayson Brogue Chelsea Boot. Saddle Brown Suede Leather Ankle Booties. Rustic Footwear With Western Kick. Wingtip Oxford Detailing, Stretch Side Gussets, Back Pull Tab To Help With Slide On / Slip On Styling. Cushioned Insoles, Leather... more

$79.00

go to store
Madewell Shoes | Madewell Bryce Ankle Boots M4674 Size 7.5 100% Leather Block Heel Suede Zip | Color: Brown/Tan | Size: 7.5

Madewell Shoes | Madewell Bryce Ankle Boots M4674 Size 7.5 100% Leather Block Heel Suede Zip | Color: Brown/Tan | Size: 7.5

Madewell 100% Leather Block Heel Ankle Boots Good As New Condition! Minimal Heel Wear (Shown) Bryce Ankle Block Heel Boots Style #M4674 Size Women’s 7.5 Fa20, 2030710 2.5 Inch Heel Tan Color, And Zipper On The Inner Ankle. Super Gorgeous Booths For... more

$65.00

go to store
Madewell Shoes | Madewell Lonny Distressed Western Ankle Boots Tan | Color: Brown/Tan | Size: 8

Madewell Shoes | Madewell Lonny Distressed Western Ankle Boots Tan | Color: Brown/Tan | Size: 8

Details: - Size: 8 - Condition: Pre-Owned, Great Condition - Ships From Los Angeles, Ca - Ships Within 1-2 Business Days more

$30.00

go to store
Madewell Shoes | Madewell Biker Boot 1937 Ankle 6 | Color: Brown | Size: 6

Madewell Shoes | Madewell Biker Boot 1937 Ankle 6 | Color: Brown | Size: 6

Madewell Short Biker Boots Feature A Buttoned Ankle Strap And Notched Top. Brown Suede Upper Shows Light Wear, 1.25" Distressed Heel. 9" Shaft And 13.5" Circumference. Rubber Sole. Great Barely-Worn Condition. Size 6, But Runs A Bit Big. Fits Me,... more

$40.00

go to store
Madewell Shoes | Madewell Ankle Boots | Color: Brown | Size: 8.5

Madewell Shoes | Madewell Ankle Boots | Color: Brown | Size: 8.5

Madewell Ankle Boots Leather Upper Leather Sole Pointy Toe Beautiful Brown Reddish Color Would Fit Size 8.5/9 more

$50.00

go to store
Madewell Shoes | Madewell Leather Cognac Ankle Boots | Color: Brown | Size: 7

Madewell Shoes | Madewell Leather Cognac Ankle Boots | Color: Brown | Size: 7

Older Madewell Leather Ankle Boots. Still Has A Lot Of Life Left Due To The High Quality. Some Wear Throughout But Overall Great Condition. True To Size more

$25.00

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

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

Sweet 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) Size 6.5 “A Never-Not-Perfect Wardrobe... more

$47.00

go to store
Madewell Shoes | Madewell Ankle Boots | Color: Brown | Size: 7.5

Madewell Shoes | Madewell Ankle Boots | Color: Brown | Size: 7.5

Super Cute Brown Ankle Boots Size 7.5 more

$50.00

go to store
Madewell Shoes | Madewell Brady Ankle Boot | Color: Brown/Tan | Size: 9

Madewell Shoes | Madewell Brady Ankle Boot | Color: Brown/Tan | Size: 9

Madewell Brady Low Cut Ankle Boot - Leather, Good Used Condition more

$50.00

go to store
Madewell Shoes | Madewell Brenner Suede Ankle Boots | Color: Brown/Tan | Size: 6

Madewell Shoes | Madewell Brenner Suede Ankle Boots | Color: Brown/Tan | Size: 6

Madewell Brenner Ankle Boots In A Mink Tan Suede Color. A Comfy Stacked Heelthis Is The Kind Of Boot You'll Reach For All Season Long. 2 1/2" Heel more

$90.00

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

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

Good Preowned Condition, See All Photos For Flaws! Bundle And Save! more

$15.00

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

Madewell Shoes | Madewell - Embossed Leather Ankle Boots | Color: Brown | Size: Various

These Brand New Dark Brown Leather Ivy Chelsea Boots From Madewell. Classic & Comfortable Features: Rounded Closed Toe Embossed Leather Cloudlift Lite Cushioned Footbed Pull-On Style Ultra-Terrain Lug Sole Approximately 3/4” Heel Approximately 5” Shaft... more

$99.00

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

Madewell Shoes | Madewell Camel Ankle Boots | Color: Brown/Tan | Size: 6.5

Preowned 2 Inch Zipper Enclosure more

$35.00

go to store
Madewell Shoes | Madewell Black Leather Heeled Ankle Boots | Color: Black/Brown | Size: 7.5

Madewell Shoes | Madewell Black Leather Heeled Ankle Boots | Color: Black/Brown | Size: 7.5

Well Loved And Well Cared For. Just Conditioned Them With Saddle Soap, But Might Be Even Better With A Polish. Perfect For Fall! more

$55.00

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

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

Madewell The Rosie Snake Embossed Leather Ankle Boots In Dark Cinnabar Multi Look No Further For Your Dream Ankle Boot. Pieced From Snake Embossed Leather, It Has A Comfy Stacked Heel And Our Mwl Cloudlift Lite Padding That Feels Like Walking On A... more

$50.00

go to store
Madewell Shoes | Madewell Charley Ankle Boots Cigar Suede And Leather | Color: Brown | Size: 7

Madewell Shoes | Madewell Charley Ankle Boots Cigar Suede And Leather | Color: Brown | Size: 7

Good, Used Condition With Plenty Of Life Left! Signs Of Wear Throughout. Would Recommend Having The Heels Resoled. more

$40.00

go to store
Madewell Shoes | Madewell 1937 The Prairie Leather Ankle Boots 7 | Color: Brown | Size: 7

Madewell Shoes | Madewell 1937 The Prairie Leather Ankle Boots 7 | Color: Brown | Size: 7

Madewell 1937 The Prairie Leather Ankle Boots Leather Upper And Lining. Lug Sole. Stacked Heel. Lace Up Closure And Pull Tab. Heel Height: Approx 3.25” Made In Italy Color: Brown Style: 50382 Us Women's Size 7 Preowned. Good Used Condition With Signs... more

$59.00

go to store
Madewell Shoes | Madewell Darrin Leather Flat Ankle Boot Booties | Color: Brown | Size: 9.5

Madewell Shoes | Madewell Darrin Leather Flat Ankle Boot Booties | Color: Brown | Size: 9.5

Cute Leather Booties With Ankle Strap Detail. Excellent Used Condition With Tons Of Life Left. Offers Welcome! Check Out The Other Madewell Items In My Closet And Bundle To Save! more

$45.00

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

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

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

$28.00

go to store
Madewell Shoes | Madewell Billie Suede Leather Side Zip Ankle Taupe Boots Size 6 | Color: Brown | Size: 6

Madewell Shoes | Madewell Billie Suede Leather Side Zip Ankle Taupe Boots Size 6 | Color: Brown | Size: 6

Madewell Billie Suede Leather Side Zip Ankle Taupe Boots Size 6 Heel Height, Approximate: 2.5" Gently Used, No Flaws Please See All Photos For Condition Details No Trades Offers Welcome more

$19.00

go to store
Madewell Shoes | Madewell Regan Chelsea Ankle Boot In English Saddle Size 7.5 | Color: Brown | Size: 7.5

Madewell Shoes | Madewell Regan Chelsea Ankle Boot In English Saddle Size 7.5 | Color: Brown | Size: 7.5

Madewell Regan Chelsea Ankle Boot In English Saddle. Made Of Rich Leather, These Cool Pull-On Boots Have Block Heels For A Little Extra Height. Color: Brown Size 7.5 Condition : Preloved, No Rips, Holes Or Tears. Normal Signs Of Wear. No Modeling... more

$70.00

go to store
Madewell Shoes | Madewell Brenner Ankle Boot In Suede | Color: Brown | Size: 10

Madewell Shoes | Madewell Brenner Ankle Boot In Suede | Color: Brown | Size: 10

Madewell Brenner Ankle Boot In Suede Size 10 Leather Upper, Lining And Sole Side Zip There Are Some Minor Scuffs To Suede Upper. Please See All Pics. Overall Still In Very Good Preowned Condition. more

$44.00

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

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

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

$50.00

go to store
Madewell Shoes | Madewell $198 The Darcy Ankle Boot In Warm Cinnamon Leather Size 7 Nn014 | Color: Brown | Size: 7

Madewell Shoes | Madewell $198 The Darcy Ankle Boot In Warm Cinnamon Leather Size 7 Nn014 | Color: Brown | Size: 7

With An Almond Toe And A Comfy Stacked Heel, These Leather Ankle Boots Go Perfectly With Any And Everything. And, Cushiness Alert: Our Mwl Cloudlift Lite Padding Feels Like Walking On A...Well, You Know.2 1/4" Heel.6" Shaft Height Leather Upper.Leather... more

$50.00

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

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

In Great Pre-Owned Condition. Very Minor Signs Of Wear. Size 7.5 Open To Offers! more

$60.00

go to store
Madewell Shoes | Madewell Brenner Suede Ankle Boots | Color: Brown/Green | Size: 8

Madewell Shoes | Madewell Brenner Suede Ankle Boots | Color: Brown/Green | Size: 8

In Overall Good Condition. They’re Perfect For Everyday Use! Smoke Free Home. Size: 8 Heel Height: 2.7 Inches Measurements Are Approximate Brown Side Zip Zipper Almond Toe Suede Block Heel Comfy Cute Casual G8041 more

$35.00

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 Regan Leather Ankle Boots | Color: Black/Brown | Size: 8.5

Madewell Shoes | Madewell Regan Leather Ankle Boots | Color: Black/Brown | Size: 8.5

Lightly Worn. Wear Seen On Soles. See Pictures And Video For Other Wear Such As Creases. No Scratches. This Cool Pull-On Boot Sports A Block Heel For A Little Extra Height, While Remaining Walking-Friendly. An Extra Layer Of Padding Makes It Even... more

$65.00

go to store
Madewell Shoes | Madewell Rosie Snake Snakeskin Printed Genuine Leather Ankle Boots | Color: Black/Brown | Size: 7.5

Madewell Shoes | Madewell Rosie Snake Snakeskin Printed Genuine Leather Ankle Boots | Color: Black/Brown | Size: 7.5

Madewell Rosie Snakeskin Print Leather Ankle Boots Brown Tone Neutral Embossed Snake Animal Print Shoes Genuine Leather Upper 4" Shaft Height 2 1/2" Stacked Heel Women's Size 7.5 Good Used Condition - Guc Fall Casual Dressy Print Snake Patterned Cold... more

$75.00

go to store
Madewell Shoes | Madewell Ankle Boots Size 9 1/2 | Color: Brown | Size: 9.5

Madewell Shoes | Madewell Ankle Boots Size 9 1/2 | Color: Brown | Size: 9.5

Madewell Brand Leather Ankle Boots With Side Zipper And Pull. Cognac Or “Saddle” Color. Some Wear As Shown In Photos. Leather Upper And Sole - Made In Brazil. Women’s Size 9 1/2 more

$35.00

go to store
Madewell Shoes | Madewell Cheetah Print Ankle Boots | Color: Brown | Size: 8

Madewell Shoes | Madewell Cheetah Print Ankle Boots | Color: Brown | Size: 8

Madewell Cheetah Ankle Boots With Chunky Heel And Zipper Up Front Meow! more

$50.00

go to store
Madewell Shoes | Madewell 1937 Suede Sandstorm Ankle Boots | Color: Brown | Size: 9

Madewell Shoes | Madewell 1937 Suede Sandstorm Ankle Boots | Color: Brown | Size: 9

Brand: 1937 For Madewell Size: Women’s 9 Color: Brown Style: Sandstorm Lace Up Ankle Bootie Condition: Preowned (Significant Wear On Heel Taps, Wear On Suede Heel Portion Of One Shoe, See Photos) more

$45.00

go to store
Madewell Shoes | Madewell Mira Side-Seam Ankle Boot In Leather | Color: Brown/Tan | Size: 9

Madewell Shoes | Madewell Mira Side-Seam Ankle Boot In Leather | Color: Brown/Tan | Size: 9

Nwt - Never Worn! Sold Out On The Madewell Site Time To Strut Your Stuff In Our Versatile New Ankle Boot. Polished And Supercute, It's Crafted Of Smooth Leather And Has A Stacked Heel For A Little Height. And, Cushiness Alert: Our Mwl Cloudlift Lite... more

$60.00

go to store

More information about Men's Shoes

Best prices on Madewell ankle boots brown shoes 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.