Best Seller
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 | Bnib New Madewell Carina Chelsea Platform Lug Sole Heeled Boots Shoes Us Sz 8.5 | Color: Brown | Size: 8.5

Madewell Shoes | Bnib New Madewell Carina Chelsea Platform Lug Sole Heeled Boots Shoes Us Sz 8.5 | Color: Brown | Size: 8.5

Brand New In Box, Never Worn Madewell Carina Chelsea Platform Lug Sole Heeled Boots! Us Size 8.5 Color: Dried Maple Item # Nh199 Originally Retails For $228 Plus Tax! Please Note: The Item For Sale Is The Dried Maple Color - The Photos On The Model Is... more

$149.00

go to store
Best Seller
Madewell Shoes | Madewell Chelsea Leather Shoes | Color: Brown | Size: 8

Madewell Shoes | Madewell Chelsea Leather Shoes | Color: Brown | Size: 8

Great Used Condition more

$65.00

go to store
Madewell Shoes | Madewell Low Chelsea Snake Booties Embossed Snakeskin Print Brown, Beige, Black | Color: Black/Cream | Size: 9

Madewell Shoes | Madewell Low Chelsea Snake Booties Embossed Snakeskin Print Brown, Beige, Black | Color: Black/Cream | Size: 9

Madewell New In Box Size 9 Chelsea Low Boots Booties Cowboy New In Box Snake Embossed Leather Outer And Leather Inner Lining Heather Multi Color With Hints Of White, Tan/Creme, Black Great Pair Of Low Heel Booties. Perfect With Skirts, Dresses, Pants... more

$55.00

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

Madewell Shoes | Madewell Dani Chelsea Lugsole Boot | Color: Brown | Size: 9.5

Color: Stable Worn Twice, Ordered The Wrong Size And Can’t Return. They’re Amazing Boots Though. Warm, With Good Tread And Great Quality Leather. more

$123.00

go to store
Madewell Shoes | Madewell Nico Taupe Suede Chelsea Boots | Color: Gray | Size: 9

Madewell Shoes | Madewell Nico Taupe Suede Chelsea Boots | Color: Gray | Size: 9

Fair Condition -Does Show Signs Of Wear On Toe/ Suede/Lining( See Pics) Still A Supercute Bootie In A Color/Style That Goes With Almost Any Thing!!! Size 9 more

$27.00

go to store
Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot Size 7.5 Western Boho Amber Brown | Color: Brown/Yellow | Size: 7.5

Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot Size 7.5 Western Boho Amber Brown | Color: Brown/Yellow | Size: 7.5

Suede Leather more

$89.00

go to store
Madewell Shoes | Madewell Sonia Ankle Low Chelsea Boots Leather | Color: Brown/Tan | Size: Various

Madewell Shoes | Madewell Sonia Ankle Low Chelsea Boots Leather | Color: Brown/Tan | Size: Various

Madewell Sonia Ankle Low Chelsea Boots Brand New In Box Retail $188 Color: Tan And Black With Snakeskin Pattern / "Heather Natural Multi" Description: An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A... more

$110.00

go to store
Madewell Shoes | Madewell Chelsea Lugsole Heeled Boots In Dried Maple Colot | Color: Brown | Size: 7.5

Madewell Shoes | Madewell Chelsea Lugsole Heeled Boots In Dried Maple Colot | Color: Brown | Size: 7.5

Originally Bought For $228. These Are In Like New Condition. more

$70.00

go to store
Madewell Shoes | Final Sale Madewell Regan Chelsea Boots Size 7.5 | Color: Brown/Tan | Size: 7.5

Madewell Shoes | Final Sale Madewell Regan Chelsea Boots Size 7.5 | Color: Brown/Tan | Size: 7.5

In Good Worn Condition, True To Size! Madewell Boots Are In A Gorgeous Cognac Leather And Have A Great 2.5” Heel That Add Height But Are Comfortable To Walk In And Go With Everything. Feature Some Wear And Slight Discoloration, As Pictured. Originally... more

$18.00

go to store
Madewell Shoes | Madewell ‘The Ivy’ Chelsea Boot In Leather | Color: Black/Tan | Size: 8.5

Madewell Shoes | Madewell ‘The Ivy’ Chelsea Boot In Leather | Color: Black/Tan | Size: 8.5

Madewell ‘The Ivy’ Chelsea Boot In Leather. Madewell Toughened Up These Classic Chelsea Boots With A Utilitarian Lug Sole. Made Of Rich Leather, They'll Look Cooler And Cooler The More You Wear 'Em. And, Cushiness Alert: The Mwl Cloudlift Lite Padding... more

$129.00

go to store
Madewell Shoes | Madewell The Ryan Chelsea Boot Black E2331 Brown Sz 6.5 | Color: Brown/Tan | Size: 6.5

Madewell Shoes | Madewell The Ryan Chelsea Boot Black E2331 Brown Sz 6.5 | Color: Brown/Tan | Size: 6.5

Brown Leather Upper Booties Light Wear On The Leather As Shown, Light Scuffing-- See Photos more

$30.00

go to store
Madewell Shoes | Madewell Sonia Chelsea Low Ankle Boots Snake Embossed Leather Natural Size 6 | Color: Black/Tan | Size: 6

Madewell Shoes | Madewell Sonia Chelsea Low Ankle Boots Snake Embossed Leather Natural Size 6 | Color: Black/Tan | Size: 6

Madewell Leather Chelsea Boots Embossed Snake Size 6 Excellent Used Condition, No Major Flaws Slip On Style Low Ankle Height Short Block Heel Slightly Pointed Toe Leather Upper/Lining/Sock Synthetic Sole more

$40.00

go to store
Madewell Shoes | Madewell Leather Citywalk Lugsole Chelsea Boot | Color: Brown | Size: 9

Madewell Shoes | Madewell Leather Citywalk Lugsole Chelsea Boot | Color: Brown | Size: 9

Pull-On Chelsea Lugsole Boots That Have Only Been Worn Once. Sole Contains Mwl Cloudlift Lite Padding. Leather Upper. Heel: 7/8” Color: English Saddle more

$80.00

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

Madewell Shoes | Madewell Chelsea Boots | Color: Black/Tan | Size: 8.5

Madewell Leather Chelsea Boots. Horse Hair Like Texture. The Soles Have Some Wear On The Outside And A Small Scuff On The Heel, But The Insoles And Shoes Are In Great Shape Overall! Size 8.5. more

$30.00

go to store
Madewell Shoes | Madewell Spencer Chelsea Pullon Boots Leather 8 | Color: Tan | Size: 8

Madewell Shoes | Madewell Spencer Chelsea Pullon Boots Leather 8 | Color: Tan | Size: 8

Good Condition Please See Pictures For Signs Of Wear more

$23.00

go to store
Madewell Shoes | Madewell Calf Hair Chelsea Boots | Color: Black/Brown | Size: 7

Madewell Shoes | Madewell Calf Hair Chelsea Boots | Color: Black/Brown | Size: 7

These Madewell Calf Hair Chelsea Boots Are Perfect For The Season! Worn Around The House For 30 Minutes One Time Other Than That Never Been Used!! In Perfect Constitution! Make An Offer! more

$80.00

go to store
Madewell Shoes | Madewell The Chelsea Shearling Ankle Boots | Color: Tan | Size: 7

Madewell Shoes | Madewell The Chelsea Shearling Ankle Boots | Color: Tan | Size: 7

Cute, Comfortable And Stylish!! Leather Upper. Has Shearling Inside Boots, Slip On Style, Elasticized Panel, No Modeling Or Trades, Good Preowned Condition With Signs Of Use more

$92.00

go to store
Madewell Shoes | Madewell Laura Chelsea Boot In Spotted Calf Hair | Color: Black/Brown | Size: 9

Madewell Shoes | Madewell Laura Chelsea Boot In Spotted Calf Hair | Color: Black/Brown | Size: 9

Madewell Laura Chelsea Boot In Spotted Calf Hair With A Taller Shaft That Fits Close To The Ankle And A Sexy High Heel, These Sleek Spotted Calf Hair Boots Look Good With Everything From Skinnies To Wide-Legs To Skirtsin Other Words, You'll Wear Them A... more

$98.00

go to store
Madewell Shoes | Madewell Nico Taupe Gray Chelsea Suede Boot | Color: Gray | Size: 8.5

Madewell Shoes | Madewell Nico Taupe Gray Chelsea Suede Boot | Color: Gray | Size: 8.5

Heel: 1” Does Have A Few Signs Of Wear, Mostly On Heel (Pictured) Otherwise In Good Condition more

$40.00

go to store
Madewell Shoes | Madewell White Grayson Brogue Chelsea Suede Leather Western Ankle Booties Size 6 | Color: Tan/White | Size: 6

Madewell Shoes | Madewell White Grayson Brogue Chelsea Suede Leather Western Ankle Booties Size 6 | Color: Tan/White | Size: 6

Brand: Madewell Style: The Grayson Brogue Chelsea Suede Leather Western Cowgirl Ankle Booties Shoes Size: 6 Color: Bone White & Tan Heel Height: 2" Condition: Pre-Owned. There Are Some Minor Blemishes On The Suede. See Pictures For Details. Otherwise,... more

$48.00

go to store
Madewell Shoes | Madewell Laura Chelsea Boot In Spotted Calf Hair Size 5.5 | Color: Brown | Size: 5.5

Madewell Shoes | Madewell Laura Chelsea Boot In Spotted Calf Hair Size 5.5 | Color: Brown | Size: 5.5

With A Taller Shaft That Fits Close To The Ankle And A Sexy High Heel, These Sleek Spotted Calf Hair Boots Look Good With Everything From Skinnies To Wide-Legs To Skirtsin Other Words, You'll Wear Them A Ton. Cushiness Alert: Our Mwl Cloudlift Lite... more

$29.00

go to store
Madewell Shoes | Madewell Size 8.5 The Carlin Shearling Chelsea Boot Ankle Boot Suede Rugged | Color: Tan | Size: 8.5

Madewell Shoes | Madewell Size 8.5 The Carlin Shearling Chelsea Boot Ankle Boot Suede Rugged | Color: Tan | Size: 8.5

Madewell Size 8.5 The Carlin Shearling Chelsea Boot Ankle Boot Suede Rugged Made Of Water-Resistant Suede With A Rugged Lug Sole, These Pull-On Chelsea Boots Are Fully Lined In Real Shearling To Up The Cozy Factor. Basically: All-Weather Boots You'll... more

$97.00

go to store
Madewell Shoes | Madewell The Laura Chelsea Boot In Spotted Calf Hair | Color: Brown/Tan | Size: 9.5

Madewell Shoes | Madewell The Laura Chelsea Boot In Spotted Calf Hair | Color: Brown/Tan | Size: 9.5

With A Taller Shaft That Fits Close To The Ankle And A Sexy High Heel, These Sleek Spotted Calf Hair Boots Look Good With Everything From Skinnies To Wide-Legs To Skirtsin Other Words, You'll Wear Them A Ton. Cushiness Alert: Our Mwl Cloudlift Lite... more

$75.00

go to store
Madewell Shoes | Madewell. The Bradley Chelsea Lugsole Boot. | Color: Brown | Size: 9

Madewell Shoes | Madewell. The Bradley Chelsea Lugsole Boot. | Color: Brown | Size: 9

Madewell. Brown Leather Pull On Boot. Size: 9. Rubber Heel Measures 1 Inch. Sold Out On The Madewell Website. more

$50.00

go to store
Madewell Shoes | Madewell, Chelsea Lugsole Boots | Color: Brown | Size: 8

Madewell Shoes | Madewell, Chelsea Lugsole Boots | Color: Brown | Size: 8

This Pair Of Boots Is Barely Worn And In Excellent Condition. Size 8, Color Dried Maple. Comes In Original Box. more

$90.00

go to store
Madewell Shoes | ! Madewell $238 The Ryan Chelsea Boots E2331 | Color: Brown | Size: Various

Madewell Shoes | ! Madewell $238 The Ryan Chelsea Boots E2331 | Color: Brown | Size: Various

Madewell $238 The Ryan Chelsea Boots Dark Chestnut Boots Shoes Leather Just Try To Complete Your Fall And Winter Outfits Without Comfortable And Stylish Boots. These Look Great With Skirts Or Pants. Style, Comfort, And Flair -- What More Could You Want... more

$55.00

go to store
Madewell Shoes | New Madewell Sonia Chelsea Snakeskin Print Boot | Color: Gray/Tan | Size: Various

Madewell Shoes | New Madewell Sonia Chelsea Snakeskin Print Boot | Color: Gray/Tan | Size: Various

Brand New Madewell Leather Sonia Chelsea Bootie. Perfect Ankle Boot With Snakeskin Print And Stacked Wood Like Heel. 1.75” Heel. Almond Shaped Toe With Tapered Heel. 3” Shaft. Fast Shipping. Bundle And Save. $188 Retail. Reviews Recommend To Size Up... more

$40.00

go to store
Madewell Shoes | Madewell Sonia Low Leather Snakeskin Chelsea Boot | Color: Black/Tan | Size: Various

Madewell Shoes | Madewell Sonia Low Leather Snakeskin Chelsea Boot | Color: Black/Tan | Size: Various

Brand New In Box - Madewell Sonia Low Leather Snakeskin Chelsea Boot. An Almond Toe And Tapered, Stacked Heel Bring A Contemporary Look To A Chelsea Boot That Serves As A Versatile Work-To-Weekend Style. These Are The Quintessential Bootie In An... more

$70.00

go to store
Madewell Shoes | Madewell Grayson Brogue Chelsea Boot | Color: Brown/Cream | Size: 7.5

Madewell Shoes | Madewell Grayson Brogue Chelsea Boot | Color: Brown/Cream | Size: 7.5

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

$40.00

go to store
Madewell Shoes | Madewell The Citywalk Lugsole Chelsea Boot In Leather English Saddle | Color: Brown/Tan | Size: 11

Madewell Shoes | Madewell The Citywalk Lugsole Chelsea Boot In Leather English Saddle | Color: Brown/Tan | Size: 11

Questions? Leave A Comment Below! more

$90.00

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

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

Brand New, Never Worn Chelsea Boots In Size 7.5 more

$100.00

go to store
Madewell Shoes | Madewell The Regan Chelsea Boot In Snake Embossed Leather Size 7 #1082 | Color: Black/Brown | Size: 7

Madewell Shoes | Madewell The Regan Chelsea Boot In Snake Embossed Leather Size 7 #1082 | Color: Black/Brown | Size: 7

Madewell The Regan Chelsea Boot In Snake Embossed Leather Size 7 Material: Snake Embossed Leather Upper, Lining And Sock , Man-Made Sole Design: Pull-On Style With An Easy On-And-Off Fit Chelsea Boot Silhouette With A 4.5" Shaft Height (Based On Size... more

$50.00

go to store
Madewell Shoes | Madewell The Kat Chelsea Boot Tan Leather Size 8 | Color: Brown/Tan | Size: 8

Madewell Shoes | Madewell The Kat Chelsea Boot Tan Leather Size 8 | Color: Brown/Tan | Size: 8

Great Boots, I Just Don’t Reach For Them. Worn A Few Times. Size 8 Make Me A Reasonable Offer And I Will Accept Bin A more

$45.00

go to store
Madewell Shoes | Madewell Grayson Brogue Western Style Chelsea Boots | Color: Brown | Size: 7.5

Madewell Shoes | Madewell Grayson Brogue Western Style Chelsea Boots | Color: Brown | Size: 7.5

Scuffs Of The Heels But Lots Of Life Left Super Comfy Just Trading In For A Different Style more

$60.00

go to store
Madewell Shoes | Madewell Carina Chelsea Ankle Boots 6.5 | Color: Tan | Size: 6.5

Madewell Shoes | Madewell Carina Chelsea Ankle Boots 6.5 | Color: Tan | Size: 6.5

Questions? Leave A Comment Below! more

$61.00

go to store
Madewell Shoes | Madewell Autumn High Chelsea Boot | Color: Brown | Size: 10

Madewell Shoes | Madewell Autumn High Chelsea Boot | Color: Brown | Size: 10

Made Of Rich Suede, These Cool Pull-On Chelsea Boots Are Cut High On The Leg To Go With Cropped Jeans And Long Skirts. 6" Shaft Height (Based On Size 7). 2" Heel. Suede Upper. Worn Once!! They Ended Up Being Too Small. more

$70.00

go to store
Madewell Shoes | Madewell Chelsea Lugsole Heeled Boots, Size 6 | Color: Brown | Size: 6

Madewell Shoes | Madewell Chelsea Lugsole Heeled Boots, Size 6 | Color: Brown | Size: 6

These Boots Are New But The Box Is A Little Damaged. Bought These Boots From Madewell.Com But It Was A Final Sale. I Liked Them Online But I Realized After Receiving Them That They’re A Bulkier Style Than I Normally Wear. Please Go To Madewell.Com To... more

$80.00

go to store
Madewell Shoes | - Madewell Ivy Chelsea Boot In Croc Embossed Leather - Dark Coffee Size 8 | Color: Brown | Size: 8

Madewell Shoes | - Madewell Ivy Chelsea Boot In Croc Embossed Leather - Dark Coffee Size 8 | Color: Brown | Size: 8

Madewell Women’s Ivy Chelsea Boots Croc Embossed Leather Brown Size 8 Brand New Without Tags more

$118.00

go to store
Madewell Shoes | Madewell The Ainsley Leather Chelsea Boot Tan Size 7.5 | Color: Tan | Size: 7.5

Madewell Shoes | Madewell The Ainsley Leather Chelsea Boot Tan Size 7.5 | Color: Tan | Size: 7.5

Madewell The Ainsley Leather Chelsea Boot Tan Size 7.5 Gently Used With Minor Wear. Slight Scuffing On Toes And Upper. Please See Last Photos. more

$50.00

go to store

More information about Men's Shoes

Best prices on Madewell shoes madewell benny chelsea, Brown 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.