You're in Men's Shoes

Narrow Search Results

  • Price Range

    $ to $
    Update>>
  • By Keyword

    Stef Chelsea Ankle Boots

    Stef Chelsea Ankle Boots

    Men's Ann Demeulemeester Stef Chelsea Ankle Boots - Black - Casual boots 100% Calf Leather, 100% Rubber. Made in Italy. more

    Lyst Marketplace

    $796.18 $473.88

    FREE shipping

    go to store
    Chelsea Ankle Boots

    Chelsea Ankle Boots

    Men's Tod's Chelsea Ankle Boots - Brown - Casual boots 100% Suede, 100% Rubber. Made in Italy. more

    Lyst Marketplace

    $587.78 $479.63

    FREE shipping

    go to store
    Chelsea Ankle Boots

    Chelsea Ankle Boots

    Men's Tod's Chelsea Ankle Boots - Black - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 2cm 100% Calf Leather, 100% Rubber. Made in Italy. more

    Lyst Marketplace

    $694.65 $566.83

    FREE shipping

    go to store
    J. Crew Shoes | J. Crew Gray Leather Ankle Chelsea Boot W/ Ankle Strap And Gold Hardware- Size 8 | Color: Gray | Size: 8

    J. Crew Shoes | J. Crew Gray Leather Ankle Chelsea Boot W/ Ankle Strap And Gold Hardware- Size 8 | C...

    J. Crew Gray Leather Chelsea Ankle Boot. Made In Italy With 2 Inch Heel, Ankle Strap And Gold Hardware. 03868 Color: Gray Size: Women's 8 more

    Poshmark

    $36.00

    go to store
    Madewell Shoes | Madewell The Ivy Chelsea Boot Mini Dot Ankle Boots Calf Hair Size 7 | Color: Brown | Size: 7

    Madewell Shoes | Madewell The Ivy Chelsea Boot Mini Dot Ankle Boots Calf Hair Size 7 | Color: Brown ...

    Madewell Ivy Chelsea Mini Dot Animal Print Ankle Boots Calf Hair Size 7 Like New more

    Poshmark

    $160.00

    go to store
    Chelsea Ankle Boots

    Chelsea Ankle Boots

    Men's Tod's Chelsea Ankle Boots - Black - Casual boots Dimensions: Heel: 4cm, Height: 14cm, Sole: 2.5cm 100% Leather, 100% Rubber, 72% Polyester, 28% Elastane. Made in Italy. more

    Lyst Marketplace

    $662.59 $572.48

    FREE shipping

    go to store
    Henry Ankle Chelsea Boot

    Henry Ankle Chelsea Boot

    Men's Tricker's Henry Ankle Chelsea Boot - Black - Casual boots 100% Leather. Made in Italy. more

    Lyst Marketplace

    $732.05 $597.36

    FREE shipping

    go to store
    Henry Country Ankle Chelsea Boot

    Henry Country Ankle Chelsea Boot

    Men's Tricker's Henry Country Ankle Chelsea Boot - Brown - Casual boots 100% Leather. Made in Italy. more

    Lyst Marketplace

    $732.05 $597.36

    FREE shipping

    go to store
    Burgundy Ankle Strap Chelsea Boots

    Burgundy Ankle Strap Chelsea Boots

    Women's Toga Burgundy Ankle Strap Chelsea Boots - Black - Ankle boots Ankle-high buffed calfskin Chelsea boots in burgundy. Signature hardware throughout. more

    Lyst Marketplace

    $605.00 $315.00

    FREE shipping

    go to store
    Larue Chelsea Ankle Boots

    Larue Chelsea Ankle Boots

    Men's Moncler Larue Chelsea Ankle Boots - Blue - Casual boots Larue Chelsea ankle boots in leather. Round toe Elasticated side panels Rear pull tab Rear logo ring Embossed logo at midsole Debossed logo at heel cap. 100% Leather. more

    Lyst Marketplace

    $795.00

    FREE shipping

    go to store
    J. Crew Shoes | J. Crew Leather Chelsea Boots Pull On Ankle Boot | Color: Black | Size: 10

    J. Crew Shoes | J. Crew Leather Chelsea Boots Pull On Ankle Boot | Color: Black | Size: 10

    J. Crew Leather Chelsea Boots Pull On Ankle Boot Black Smooth Buttery Leather Size 10 In Great Condition! Finish Your Fall Look In The Smooth Leather J.Crew Chelsea Lexi Boot Featuring A Breathable Leather Lining And Lightly Cushioned, ... more

    Poshmark

    $125.00

    go to store
    Madewell Shoes | Madewell Ivy Croc Leather Chelsea Boots Lug Sole Platform Ankle Boots Like New | Color: Brown | Size: 8

    Madewell Shoes | Madewell Ivy Croc Leather Chelsea Boots Lug Sole Platform Ankle Boots Like New | Co...

    Madewell Size 8 The Ivy Croc Embossed Leather Chelsea Boots Ankle Boots In Brown Platform Utilitarian Lug Soles In Excellent Almost Like New Condition. Very Clean Inside & Out. Tags: Classic Chunky Lug Soles Neutral Versatile Business ... more

    Poshmark

    $75.00

    go to store
    Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond Color 7 | Color: Brown/Tan | Size: 7

    Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond Color 7 | Color: Br...

    Details Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side Zipper ... more

    Poshmark

    $128.00

    go to store
    Free People Shoes | Free People James Chelsea Boots White Leather Lug Sole Ankle Boots In Bone 40 | Color: White | Size: 9

    Free People Shoes | Free People James Chelsea Boots White Leather Lug Sole Ankle Boots In Bone 40 | ...

    Brand: Free People Style: James Chelsea Boots Heeled Ankle Booties Color: White Material: Leather With Rubber Gum Sole Size: Eu 40, Fits Like A 9 Has A Slightly Narrow Fit In My Opinion, Though I Do Better With Wider Fit Shoes Condition: ... more

    Poshmark

    $54.00

    go to store
    Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot J8292, Western Cut Ankle Boot. | Color: Brown/Tan | Size: 8

    Madewell Shoes | Madewell The Grayson Brogue Chelsea Boot J8292, Western Cut Ankle Boot. | Color: Br...

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

    Poshmark

    $54.00

    go to store
    Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond 7 | Color: Brown/Tan | Size: Various

    Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond 7 | Color: Brown/Ta...

    Details Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side Zipper ... more

    Poshmark

    $128.00

    go to store
    Free People Shoes | Free People Essential Chelsea Boots In Natural Cream Ankle Boots Size 38 Euc | Color: Cream | Size: 8

    Free People Shoes | Free People Essential Chelsea Boots In Natural Cream Ankle Boots Size 38 Euc | C...

    Free People Tan Leather Ankle Boots Made In Spain Size 38/8 Euc No Box more

    Poshmark

    $90.00

    go to store
    Burberry Shoes | New Burberry Chelsea Boots Check Leather Ankle Boots | Color: Black | Size: 7

    Burberry Shoes | New Burberry Chelsea Boots Check Leather Ankle Boots | Color: Black | Size: 7

    New Burberry Check Chelsea Leather Ankle Boots Brand New In Box With Tags Full Set Eu 37 - Heel Measures Approximately 35mm/ 1.5 Inches - Black Leather - Pull On - Made In Italy 100% Brand New Authentic Guaranteed Professional Business ... more

    Poshmark

    $649.00

    go to store
    Gucci Shoes | Gucci Marmont Double G Mateless Leather Chelsea Ankle Boots | Color: Black | Size: 10.5

    Gucci Shoes | Gucci Marmont Double G Mateless Leather Chelsea Ankle Boots | Color: Black | Size: 10....

    Gucci Marmont Double G Mateless Leather Chelsea Ankle Boots Size 40.5 Black Leather Matelasse Leather Double G 2 Inches Made In Italy Comes With Original Box, Tags, Dust Bags, Booklets more

    Poshmark

    $950.00

    go to store
    Levi's Shoes | Levis Mens Keith Pull On Chelsea Ankle Boots Tan/ Brown Suede Size 13 M Us (Nwt) | Color: Tan | Size: 13

    Levi's Shoes | Levis Mens Keith Pull On Chelsea Ankle Boots Tan/ Brown Suede Size 13 M Us (Nwt) | Co...

    Complement Your Classic Look With The New Keith Suede Chelsea Boot From Levi’s! These Handsome Chelsea Boots Feature Soft Suede Uppers With Dual Elastic Gore For Easy On And Off And Memory Foam Footbed For Lasting Comfort. more

    Poshmark

    $50.00

    go to store
    Madewell Shoes | Madewell Nadine Ankle Chelsea Boots Spotted Calf Skin Sz 7.5 | Color: Black/Brown | Size: 7.5

    Madewell Shoes | Madewell Nadine Ankle Chelsea Boots Spotted Calf Skin Sz 7.5 | Color: Black/Brown |...

    Used Pair Of Madewell Nadine Ankle Chelsea Boots In Size 7.5. These Are A Spotted Calf Hair Upper. There Is A Little Wear On The Points Of The Toes. Minimal Heel Wear. Please See Photos more

    Poshmark

    $35.00

    go to store
    Madewell Shoes | Bnib Madewell Sonia Snakeskin Chelsea Ankle Boots 6 | Color: Black/Tan | Size: 6

    Madewell Shoes | Bnib Madewell Sonia Snakeskin Chelsea Ankle Boots 6 | Color: Black/Tan | Size: 6

    Python Snake Print Heather Natural Leather Chelsea Booties With Almond Toe And Stacked Wooden Heel, Comes With Box 1.75'' Heel 3'' Shaft Pull-On With Elastic Gore Insets Tapered, Stacked Heel Cushioned Footbed Leather Upper Leather Lining more

    Poshmark

    $55.00

    go to store
    Free People Shoes | Free People Brooks Chelsea Ankle Boots | Color: Green | Size: 6.5

    Free People Shoes | Free People Brooks Chelsea Ankle Boots | Color: Green | Size: 6.5

    Leather Upper Ankle-High Chelsea Boot Shaft Zipper Closure Lightly Cushioned Footbed Lug Outsole Pull-On New Without Box Size 36.5 (6.5) more

    Poshmark

    $110.00

    go to store
    Free People Shoes | Free People Maverick Black Leather Chelsea Boots Western Ankle Booties | Color: Black | Size: 8

    Free People Shoes | Free People Maverick Black Leather Chelsea Boots Western Ankle Booties | Color: ...

    Reposhing This Item I Purchased From @Pinetreeposh. Loved It, But They Are Too Small I’m Usually A 9 Or 9.5. These Fit So Snug, I Would Compare Them To An 8, Maybe An 8.5. more

    Poshmark

    $100.00

    go to store
    Madewell Shoes | Madewell Carina Ankle Chelsea Boot Bootie | Color: Brown | Size: 7

    Madewell Shoes | Madewell Carina Ankle Chelsea Boot Bootie | Color: Brown | Size: 7

    Excellent Condition! Size 7 Cognac Color more

    Poshmark

    $85.00

    go to store
    Gucci Shoes | Gucci Worsh Black Leather Chelsea Ankle Boots | Color: Black | Size: 11

    Gucci Shoes | Gucci Worsh Black Leather Chelsea Ankle Boots | Color: Black | Size: 11

    Only Wore Once To Big It Comes With Original Box And Dust Bags As Well In Great Condition No Scratches Or Marks more

    Poshmark

    $950.00

    go to store
    Anthropologie Shoes | Anthropologie Silent D Uvika Chelsea Suede Leather Ankle Boots In Honey Brown | Color: Brown/Tan | Size: 7

    Anthropologie Shoes | Anthropologie Silent D Uvika Chelsea Suede Leather Ankle Boots In Honey Brown ...

    Reach New Heights In A Pair Where Elevated Neutrals And A Wedge Heel Take Center Stage. In Great Preowned Condition. Minor Wear To The Outer Sole. One Mark At The Inner Side Gore Panel Of The Left Boot. See Photos. Suede Leather Upper ... more

    Poshmark

    $75.00

    go to store
    Gucci Shoes | Authentic Gucci Horsebit Chain Leather Chelsea Black Ankle Boot 38.5 New | Color: Black | Size: 38.5

    Gucci Shoes | Authentic Gucci Horsebit Chain Leather Chelsea Black Ankle Boot 38.5 New | Color: Blac...

    This Is A Fabulous Pair Of Authentic Gucci Flores Calfskin Horsebit Chain Ankle Boots Size 38.5 In Black. These Boots Are Mid Length On The Leg And Crafted Of Soft Black Lambskin Leather. These Boots Feature A 1.5 Inch Heel, A Gold ... more

    Poshmark

    $750.00

    go to store
    Free People Shoes | Free People "Chelsea* Puffer Ankle Boots (New) | Color: Black/Silver | Size: 40 Eu / 9.5 Us

    Free People Shoes | Free People "Chelsea* Puffer Ankle Boots (New) | Color: Black/Silver | Size: 40 ...

    Stud Details And A Smart Cap Toe Kick This Chelsea Boot Up A Notch. *** No Box! Leather Upper With Shiny Cap Toe And Heel Pull-On Styling With Elastic Side Panels Lightly Cushioned Footbed 1-1/2" Heel Height The Last Picture Is A Stock ... more

    Poshmark

    $90.00

    go to store
    Anthropologie Shoes | Anthropologie Chelsea Ankle Boots | Color: Pink | Size: 10

    Anthropologie Shoes | Anthropologie Chelsea Ankle Boots | Color: Pink | Size: 10

    Pre-Owned. Good Condition. No Box. Please See All Pictures As These Are The Exact Shoes You Will Receive. **There Is Some Stains/Scuffs On The Toe Fronts. See Last Picture. Womens Size 10 Usps Shipping. Same Day Or Next Day Shipping. ... more

    Poshmark

    $30.00

    go to store
    Free People Shoes | Free People Castillo Chelsea Boots Ankle | Size 37 (6-6.5) | Color: Brown | Size: 6.5

    Free People Shoes | Free People Castillo Chelsea Boots Ankle | Size 37 (6-6.5) | Color: Brown | Size...

    Rare Find! Free People Castillo Chelsea Boots Ankle | Size 37 (6-6.5) Made In Portugal With Real Patent Leather And Meant To Look Distressed. Wooden Sole And Chunky Metal Accents. Slight Creases Near Toes But Not Not Effect The ... more

    Poshmark

    $89.00

    go to store
    J. Crew Shoes | J. Crew Chelsea Leather Ankle Boot, Size 9 | Color: Black | Size: 9

    J. Crew Shoes | J. Crew Chelsea Leather Ankle Boot, Size 9 | Color: Black | Size: 9

    These Are In Great Condition Although They Are Used. I Did Not Find Any Scuffs Except A Few On The Heel - Please See The Last Picture. Leather. Size 9. Black. more

    Poshmark

    $40.00

    go to store
    Madewell Shoes | Madewell Chelsea Boots 6 Tan The Henry Lugsole Suede Leather Pull On Ankle Zip | Color: Tan | Size: 6

    Madewell Shoes | Madewell Chelsea Boots 6 Tan The Henry Lugsole Suede Leather Pull On Ankle Zip | Co...

    Condition: Pre-Owned With Natural Cosmetic Wear Noted, See Photos. Size: 6 Color: Tan Material: Suede Leather Upper Measurements: Shaft Height: 4.5 In Heel Height: 1.75 In Made Of Textured Suede With A Comfy Elasticized Shaft And Grippy ... more

    Poshmark

    $20.00

    go to store
    Free People Shoes | Free People James Chelsea Cream Lugged Sole Chunky Ankle Boot, Size 37.5 | Color: Cream | Size: 37.5 (Us 7)

    Free People Shoes | Free People James Chelsea Cream Lugged Sole Chunky Ankle Boot, Size 37.5 | Color...

    Relatively Lighter Wear, Pre-Owned Condition, But Not Totally Without Blemish. Color: Cream Leather Vamp Side Zipper For Ease Of On And Off Cushioned Interior Foot Bed Expandable Accent Inset For Optimal Comfort Fit Approximate ... more

    Poshmark

    $75.00

    go to store
    Free People Shoes | Free People James Chelsea Ankle Boots In White New In Box | Color: Black/White | Size: 10

    Free People Shoes | Free People James Chelsea Ankle Boots In White New In Box | Color: Black/White |...

    Love Love These Boots, They Were Just Too Small For Me. Questions? Leave A Comment Below! more

    Poshmark

    $120.00

    go to store
    Anthropologie Shoes | Hoss Intropia - Tan Suede Ankle Chelsea Boots, 9 | Color: Brown/Tan | Size: 9

    Anthropologie Shoes | Hoss Intropia - Tan Suede Ankle Chelsea Boots, 9 | Color: Brown/Tan | Size: 9

    Hoss Intropia Tan Suede Ankle Boots With Back Zip Detail And Stacked Wooden Heel Pre-Owned - Fair Condition, Denim Dye Spot Transfers At The Edges On Top, Can Be Professionally Cleaned For Additional Cost, Added Vibram Sole, See Images, ... more

    Poshmark

    $199.00

    go to store
    J. Crew Shoes | J Crew Olive Green Pull On Chelsea Rain Boot Ankle 7 | Color: Green | Size: 7

    J. Crew Shoes | J Crew Olive Green Pull On Chelsea Rain Boot Ankle 7 | Color: Green | Size: 7

    J Crew Olive Green Pull On Chelsea Rain Boot Ankle 7 Preowned Has Some Wear See Photos Shoe3 more

    Poshmark

    $32.00

    go to store
    Free People Shoes | Free People Atlas Black Puffer Chelsea Ankle Boots | Color: Black | Size: 8.5

    Free People Shoes | Free People Atlas Black Puffer Chelsea Ankle Boots | Color: Black | Size: 8.5

    Please Read Description Above About This Brand New Puffer Boot! more

    Poshmark

    $112.00

    go to store

    More information about Men's Shoes

    Best prices on River island ankle boots chelsea 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.