You're in Men's Shoes

Narrow Search Results

  • Price Range

    $ to $
    Update>>
  • By Keyword

    Best Seller
    J. Crew Shoes | J.Crew Chelsea Boots Black Leather Ankle Heel Classic 9 $250 | Color: Black | Size: 9

    J. Crew Shoes | J.Crew Chelsea Boots Black Leather Ankle Heel Classic 9 $250 | Color: Black | Size: 9

    J.Crew Chelsea Boots Black Leather Ankle Heel Classic 9 $250. Excellent Condition Minimal Wear Size 9 Original Box Included Wardrobe Staple Style Similar To Saint Laurent Ysl Wyatt Boots more

    $165.00

    go to store
    Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Womens

    Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Womens

    Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... more

    $69.99

    go to store
    Best Seller
    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

    $694.65 $566.83

    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

    $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: 4cm, Height: 14cm, Sole: 2.5cm 100% Leather, 100% Rubber, 72% Polyester, 28% Elastane. Made in Italy. more

    $662.59 $572.48

    FREE shipping

    go to store
    Lou Suede Ankle Boots - Black - Saint Laurent Boots

    Lou Suede Ankle Boots - Black - Saint Laurent Boots

    Women's Saint Laurent Lou Suede Ankle Boots - Black If there's one shoe to invest in, it's ankle boots. Once you've found the perfect pair you'll wear them season after season. SAINT LAURENT's classic 'Lou' pair has been made in Italy from supple suede... more

    $1,063.00 $554.00

    FREE shipping

    go to store
    Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

    Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

    Reposhing This Item I Purchased From @Cooldudz. Used 1x For A Wedding Rehearsal And Now That I Am Working From Home I Don’t Wear/Need Heels Anymore. Loved Them, Fit Well And Very Stylish. more

    $50.00

    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 | Color: Gray | Size: 8

    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

    $36.00

    go to store
    WIDE FIT Darcy Chelsea Boot - black

    WIDE FIT Darcy Chelsea Boot - black

    Elevate your look with the Darcy Chelsea Boot. Perfect for AM to PM, enjoy the stylish detailing and ultra comfortable cushioned insoles. Key Features Include:- Rounded toe ankle boot- Wide width fit- Side zip closure- Cloudwalkers cushioned insole-... more

    $99.99 $69.99

    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

    $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

    $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

    $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

    $795.00

    FREE shipping

    go to store
    Wyatt Chelsea Boots

    Wyatt Chelsea Boots

    Men's Saint Laurent Wyatt Chelsea Boots - Brown - Casual boots Dimensions: Heel: 4cm 100% Calfskin Leather. Made in Italy. more

    $945.79 $726.36

    FREE shipping

    go to store
    Wyatt Ankle Boots

    Wyatt Ankle Boots

    Men's Saint Laurent Wyatt Ankle Boots - Brown - Casual boots Dimensions: Heel: 3.5cm, Height: 17.5cm, Sole: 1cm 100% Suede Leather. Made in Italy. more

    $1,124.71 $899.76

    FREE shipping

    go to store
    Lukas 40 Ankle Boots

    Lukas 40 Ankle Boots

    Men's Saint Laurent Lukas 40 Ankle Boots - Black - Casual boots Black leather Lukas 40 ankle boots from Saint Laurent featuring an ankle length, a pointed toe, a side zip fastening, a chunky low block heel and a metallic pull tab. more

    $1,068.19 $853.67

    FREE shipping

    go to store
    Ankle Boots

    Ankle Boots

    Men's Saint Laurent Ankle Boots - Black - Casual boots Calfskin Ankle Boots by Saint Laurent, slip-on style, extended toe, elasticated side bands, block heel. Upper: 100% Calf leather bos taurus. Sole: 100% Calf leather bos taurus. Made in Italy.... more

    $844.00 $759.60

    go to store
    Wyatt Ankle Boots

    Wyatt Ankle Boots

    Men's Saint Laurent Wyatt Ankle Boots - Black - Formal boots Dimensions: Heel: 3cm 100% Calfskin Leather. Made in Italy. more

    $956.48 $598.64

    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, Stationed Insole... more

    $125.00

    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 | Color: White | Size: 9

    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: New, No Box.... more

    $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/Tan | Size: Various

    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 Closure Cushioned... more

    $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 | Color: Cream | Size: 8

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

    $90.00

    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: Brown/Tan | Size: 7

    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 Closure Cushioned... more

    $128.00

    go to store
    Madewell Shoes | Madewell The Grayson Chelsea Black Boot Size 9 Bootie Ankle Boots | Color: Black | Size: 9

    Madewell Shoes | Madewell The Grayson Chelsea Black Boot Size 9 Bootie Ankle Boots | Color: Black | Size: 9

    Madewell The Grayson Chelsea Black Boot Size 9 Bootie Ankle Boots Wear To Toes- Scuffing. Rubbing. Minor Scratching At Heels. Gently Used. Good Condition. Our Design Team Took Age-Old Western Boot Detailsa Stacked Raw Leather Heel, A Pointy Toeand Cut... more

    $50.00

    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 | Color: Brown | Size: 8

    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 Casual Office... more

    $75.00

    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: 6.5

    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 Functionality Of The... more

    $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

    $40.00

    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

    $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

    $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: Black | Size: 8

    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

    $100.00

    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

    $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 | Color: Brown/Tan | Size: 7

    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 Leather Lining... more

    $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: Black | Size: 38.5

    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 Horsebit, Silver... more

    $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 Eu / 9.5 Us

    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 Photo. Eu Size... more

    $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. Please Follow As... more

    $30.00

    go to store
    Anthropologie Shoes | Anthropologie Taupe Tan Brown Leather Pull-On Chelsea Ankle Boots Size 9 | Color: Brown/Tan | Size: 9

    Anthropologie Shoes | Anthropologie Taupe Tan Brown Leather Pull-On Chelsea Ankle Boots Size 9 | Color: Brown/Tan | Size: 9

    Anthropologie Ankle Boots - Leather Upper And Lining - Pull-On Style - Stacked Heels - Taupe/Tan - Size 9 Gently Pre-Owned; Some Light Scrapes To Heels As Shown. more

    $35.00

    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: 10.5

    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

    $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) | Color: Tan | Size: 13

    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

    $50.00

    go to store
    Madewell Shoes | Madewell Size 9 Brynn Ankle Heeled Chelsea Boot With Velvet Trim | Color: Black | Size: 9

    Madewell Shoes | Madewell Size 9 Brynn Ankle Heeled Chelsea Boot With Velvet Trim | Color: Black | Size: 9

    Madewell Size 9 Brynn Ankle Heeled Chelsea Boot With Velvet Trim 1 1/2” Heel 4 1/2” Shaft Height Leather, Suede Upper Man-Made Sole Style # Mb834 Slight Scuffing On Rim Of Front Toes But Not Noticeable When Wearing more

    $32.00

    go to store
    Madewell Shoes | Madewell Ainsley Black Leather Chelsea Pull On Ankle Boots Size 9.5 | Color: Black | Size: 9.5

    Madewell Shoes | Madewell Ainsley Black Leather Chelsea Pull On Ankle Boots Size 9.5 | Color: Black | Size: 9.5

    Black Leather Upper Chelsea Side Panels Ankle Height Really Great Condition Gently Worn more

    $36.00

    go to store

    More information about Men's Shoes

    Best prices on Saint laurent 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.