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 | Madewell Chelsea Boots The Nico Size 8.5 Leather Gray Shoes E2240 | Color: Gray | Size: 8.5

Madewell Shoes | Madewell Chelsea Boots The Nico Size 8.5 Leather Gray Shoes E2240 | Color: Gray | Size: 8.5

Madewell The Nico Cheslea Leather Boots Size 8.5 Castle Rock Shoes E2240 Gray See All Photos For Measurements Excellent Pre-Loved Condition, No Flaws, Please See All Photos For Details Feel Free To Ask Any Questions more

$53.00

go to store
Best Seller
Madewell Shoes | Madewell - Chelsea Ridgefield Lug Sole Mule Loafer Heeled Shoes, Size 7 (Black) | Color: Black | Size: 7

Madewell Shoes | Madewell - Chelsea Ridgefield Lug Sole Mule Loafer Heeled Shoes, Size 7 (Black) | Color: Black | Size: 7

Rare! Sample - Madewell - Lug Sole Clog Loafer Chunky Mules, Size 7 (Black) Slip-On Loafer Mules With 1.5 Heel. Cutout Lug Sole. Chic And Modern. These Are A Sample Of The Ridgefield Chelsea. These Are Marked "Sample". Condition: Euc, Light Wear On The... more

$67.00

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
Madewell Shoes | Madewell The Ryan Chelsea Boots Size 5 Black Leather Shoes $238 #E2331 | Color: Black | Size: 5

Madewell Shoes | Madewell The Ryan Chelsea Boots Size 5 Black Leather Shoes $238 #E2331 | Color: Black | Size: 5

Madewell The Ryan Chelsea Boots Size 5 Black Leather Shoes $238 #E2331. more

$40.00

go to store
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 The Grayson Chelsea Boot | Color: Black | Size: 8

Madewell Shoes | Madewell The Grayson Chelsea Boot | Color: Black | Size: 8

Madewell The Greyson Chelsea Boot. Black Leather. 1.25” Stacked Heel. Size 8. Great Pre-Owned Condition. No Flaws In The Leather. Minor Scuffing On Tread. Reposhing This Item I Purchased From @Ivyella. Loved It, But Ready To Rotate For Something New.... more

$49.00

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 Chelsea Rain Boots | Color: Black | Size: 7

Madewell Shoes | Madewell Chelsea Rain Boots | Color: Black | Size: 7

Worn Once more

$40.00

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 The Ainsley Chelsea Boot J8295 Leather | Color: Black | Size: Various

Madewell Shoes | Madewell The Ainsley Chelsea Boot J8295 Leather | Color: Black | Size: Various

Crafted From Buttery Leather, This Updated Chelsea Boot Has A Pared Down Look Thanks To The Sleek Covered Insets. Cushiness Alert: We've Added An Extra Layer Of Padding To Make Them Even Easier On The Feet. Logo On Sole Marked To Prevent Retail Store... more

$62.00

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 Sonia Low Leather Chelsea Boot | Color: Red | Size: 6

Madewell Shoes | Madewell Sonia Low Leather Chelsea Boot | Color: Red | Size: 6

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 3" Shaft Pull-On Style With Elastic Gore Insets Cushioned Footbed Leather Upper And Lining/Synthetic Sole... more

$65.00

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 Block Heel Chelsea Boot | Color: Black | Size: 7.5

Madewell Shoes | Madewell Block Heel Chelsea Boot | Color: Black | Size: 7.5

Great Everyday Boot. Good Worn Condition, No Significant Marks Or Damage more

$61.00

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 Wyckoff Chelsea Suede Lugsole Boot | Color: Black/Gray | Size: 8

Madewell Shoes | Madewell Wyckoff Chelsea Suede Lugsole Boot | Color: Black/Gray | Size: 8

New Without Box. Ready For All Your Supercute Fall Fits, These Suede Chelsea Boots Have Stretchy Gores And Wear-Alllday-Everywhere Chunky Lugsoles. Suede Upper. Leather Lining. Man-Made Sole. more

$125.00

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 Sonia Low Leather Snakeskin Chelsea Boot | Color: Black/Cream | Size: 10

Madewell Shoes | Madewell Sonia Low Leather Snakeskin Chelsea Boot | Color: Black/Cream | Size: 10

Madewell Sonia Low Leather Snakeskin Chelsea Boot. Size 10. Nib. Questions? Leave A Comment Below! more

$85.00

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 The Benning Chelsea Boot In True Black Leather | Color: Black | Size: 9

Madewell Shoes | Madewell The Benning Chelsea Boot In True Black Leather | Color: Black | Size: 9

Madewell The Benning Chelsea Boot In True Black Leather Size 9 In Good Condition Features: Stylish, Leather, Neutral, Madewell, Winter, Fall, Fall Fashion, Trendy, Booties, Boots, Staple, Timeless, Everyday, Everyday Style, Chelsea Boot Size: Womens 9 more

$100.00

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 Black Chelsea Boots | Color: Black | Size: 8

Madewell Shoes | Madewell Black Chelsea Boots | Color: Black | Size: 8

Used In Good Condition Chelsea Boots From Madewell. Size 8, Fit True To Size For Me. Few Minor Scuff Marks, But Worn Less Than 10 Times. From A Non Smoking Home. Very Comfortable! more

$40.00

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 | Madewell Chelsea Boot | Color: Black | Size: 9

Madewell Shoes | Madewell Chelsea Boot | Color: Black | Size: 9

Madewell Chelsea Boot. Used Condition more

$45.00

go to store

More information about Men's Shoes

Best prices on Madewell shoes madewell benny chelsea, 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.