Best Seller
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
Chelsea Boots, Ankle Boots

Chelsea Boots, Ankle Boots

Men's Santoni Chelsea Boots, Ankle Boots - Blue - Casual boots Chelsea' suede ankle boots with elastic side inserts, contrast lining, back logo tab and rubber sole. Colours: Blue Composition: 100% leather Dimension: UK MEN MPN: MGSI13414SMAISYWU60.... more

$696.00 $454.00

go to store
Best Seller
Chelsea Ankle Boots

Chelsea Ankle Boots

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

$615.69 $502.41

FREE shipping

go to store
Slip-on Chelsea Ankle Boots

Slip-on Chelsea Ankle Boots

Men's Tod's Slip-on Chelsea Ankle Boots - Brown - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 1.5cm 100% Calf Leather, 100% Rubber. Made in Italy. more

$727.64 $593.75

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 | 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
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
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

$727.64 $593.75

FREE shipping

go to store
Shield Square-toe Chelsea Ankle Boots

Shield Square-toe Chelsea Ankle Boots

Men's Burberry Shield Square-toe Chelsea Ankle Boots - Black - Casual boots 65% Calf Leather, 25% Polyester, 10% Rubber, Lining: 70% Calf Leather, 12% Polyester, 10% Goatskin Leather, 8% Rubber. Made in Italy. more

$1,159.18 $927.34

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

$694.06 $599.66

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

$766.82 $625.73

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

$766.82 $625.73

FREE shipping

go to store
Stef Chelsea Ankle Boots

Stef Chelsea Ankle Boots

Men's Ann Demeulemeester Stef Chelsea Ankle Boots - Black - Casual boots Synonymous with timeless elegance, the Chelsea boot gets a low-key update from Ann Demeulemeester. A menswear classic, they will go with a navy or grey suit, or with jeans and a... more

$833.99 $512.40

FREE shipping

go to store
Beige Sesto Boots

Beige Sesto Boots

Men's Diemme Beige Sesto Boots - Black - Casual boots Ankle-high padded suede and grained leather boots in beige. more

$525.00 $263.00

go to store
Black Sesto Boots

Black Sesto Boots

Men's Diemme Black Sesto Boots - Casual boots Ankle-high padded suede and grained leather boots in black. more

$525.00 $315.00

FREE shipping

go to store
Pink Sesto Boots

Pink Sesto Boots

Men's Diemme Pink Sesto Boots - Black - Casual boots Ankle-high padded suede and grained leather boots in pink and beige. more

$525.00 $263.00

go to store
Madewell Shoes | Madewell The Carina Boot In Snake Embossed Leather Ankle Chelsea Boot Booties | Color: Black/Yellow | Size: 6

Madewell Shoes | Madewell The Carina Boot In Snake Embossed Leather Ankle Chelsea Boot Booties | Color: Black/Yellow | Size: 6

Excellent Condition Madewell The Carina Boot In Snake Embossed Leather Ankle Chelsea Boot Booties Brand: Madewell Size: Women’s Size 6 Style: 2030756 Carina Color: Burnt Clay Multi 1.5” Stacked Block Heel 5.5” Tall Leather Upper Snakeskin Print Yellow... more

$68.00

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 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 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 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
Black O-ring Chelsea Boots

Black O-ring Chelsea Boots

Men's Marni Black O-ring Chelsea Boots - Casual boots Ankle-high patent leather Chelsea boots in black. more

$1,250.00 $850.00

FREE shipping

go to store
Black 2976 Gothic Americana Quad Chelsea Boots

Black 2976 Gothic Americana Quad Chelsea Boots

Men's Dr. Martens Black 2976 Gothic Americana Quad Chelsea Boots - Casual boots Ankle-high polished leather Chelsea boots in black. more

$210.00

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
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: Cream | Size: 37.5 (Us 7)

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 Measurements 6” Shaft... more

$75.00

go to store
Madewell Shoes | Madewell Ainsley Brown Leather Chelsea Ankle Boots Size 6.5 | Color: Brown | Size: 6.5

Madewell Shoes | Madewell Ainsley Brown Leather Chelsea Ankle Boots Size 6.5 | Color: Brown | Size: 6.5

Madewell Ainsley Brown Leather Chelsea Ankle Boots Size 6.5 Gently Used, Signs Of Wear Are On The Sole. Leather Is In Great Condition. more

$65.00

go to store
Free People Shoes | Free People Oxblood Carmel Leather Block Heel Platform Chelsea Ankle Boots 7.5 | Color: Red | Size: 7.5

Free People Shoes | Free People Oxblood Carmel Leather Block Heel Platform Chelsea Ankle Boots 7.5 | Color: Red | Size: 7.5

These Are Stylish, Comfortable, And Timeless Chelsea Boots From Free People. They Are Crafted From High Quality Genuine Leather That's Slightly Aged And Distressed. Gorgeous Dark Red/Burgundy/Oxblood Color. - Elastic Side Panels For An Easy Pull-On... more

$125.00

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
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, Ask Questions,... more

$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

$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

$112.00

go to store
Free People Shoes | Free People Atlas Chelsea Black Leather Suede Ankle Boots Minimalist Grunge | Color: Black | Size: 40eu

Free People Shoes | Free People Atlas Chelsea Black Leather Suede Ankle Boots Minimalist Grunge | Color: Black | Size: 40eu

Free People Atlas Chelsea Black Leather Suede Ankle Boots Minimalist Grunge Size 40 Gently Used more

$65.00

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
Coach Shoes | Coach Suffolk Patchwork Black Leather Chelsea/Ankle Boots, Snakeskin, Calf, 6.5b | Color: Black | Size: 6.5

Coach Shoes | Coach Suffolk Patchwork Black Leather Chelsea/Ankle Boots, Snakeskin, Calf, 6.5b | Color: Black | Size: 6.5

Coach Suffolk Patchwork Black Leather Chelsea/Ankle Boots, Snakeskin, Calf, 6.5b Euc 1.25” Heel more

$46.00

go to store
Madewell Shoes | Madewell Sonia Low Snakeskin Chelsea Ankle Boots Size 5.5 | Color: Black/Cream | Size: 5.5

Madewell Shoes | Madewell Sonia Low Snakeskin Chelsea Ankle Boots Size 5.5 | Color: Black/Cream | Size: 5.5

Madewell Sonia Low Snakeskin Chelsea Ankle Boots Size 5.5 - Snake Print - Leather Uppers And Lining Flaws: Small Scratch On Front Of Ankle (See Close Up Photo). Offers Welcome! Bundle Items In My Closet For The Best Deal! more

$25.00

go to store
Free People Shoes | New Free People Atlas Chelsea Puffer Ankle Boot 39.5 9.5 Black | Color: Black | Size: 39.5eu

Free People Shoes | New Free People Atlas Chelsea Puffer Ankle Boot 39.5 9.5 Black | Color: Black | Size: 39.5eu

New & Never Worn, No Box, Please Review Photos Size 39.5 / 9.5 Say Hello To The Perfect, Most Versatile Boot. The Ankle Height Makes This Style Easily Transition From Day To Night. Wear Them With Your Favorite Skinny Jeans And Tee For A More Laid Back... more

$98.00

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

More information about Men's Shoes

Best prices on Sesto meucci 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.