Men's Chelsea Boots

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Generic
$44.99

Territory Mens Faux Leather High Top Round Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape:... roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/Man-madeAll measurements are approximate and may vary by size. read more

Generic
$44.99

Territory Mens Faux Leather High Top Round Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape:... roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/Man-madeAll measurements are approximate and may vary by size. read more

Generic
$44.91

Territory Mens Faux Leather High Top Round Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape:... roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/Man-madeAll measurements are approximate and may vary by size. read more

Naot
$209.95

The Business Chelsea Boot is classically good looking. It'll look great whether you're in with jeans or slacks. The attractive lea...ther upper has a rounded toe and double elastic insets, for easy on and off, as well as a comfortable fit. The removable... read more

Vionic with Orthaheel Technology
$189.95

The Vionic with Orthaheel Technology Kingsley Chelsea Boot is a timeless style favorite, with twin gore panels for comfort and an ...ankle-high silhouette. This chelsea boot's sophisticated detailing gives it a polished vibe. Genuine leather-skinned... read more

Dr. Martens
$120.00 $95.99

The Lyme Chelsea Boot is built to last with an unlined and deconstructed design. Subtle rib detail around heel Air cushioned sole.... read more

Generic
$44.99

Territory Mens Faux Leather High Top Round Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape:... roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/Man-madeAll measurements are approximate and may vary by size. read more

Generic
$44.99

Territory Mens Faux Leather High Top Round Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape:... roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/Man-madeAll measurements are approximate and may vary by size. read more

Naot
$209.95

The Business Chelsea Boot is classically good looking. It'll look great whether you're in with jeans or slacks. The attractive lea...ther upper has a rounded toe and double elastic insets, for easy on and off, as well as a comfortable fit. The removable... read more

Generic
$44.99

Territory Mens Faux Leather High Top Round Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape:... roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/Man-madeAll measurements are approximate and may vary by size. read more

Generic
$44.99

Territory Mens Faux Leather High Top Round Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape:... roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/Man-madeAll measurements are approximate and may vary by size. read more

Frye
$298.00

Frye Men's Sam Leather Chelsea Boots. This sleek ankle boot pairs perfectly with tailored, straight leg jeans or slacks. Crafted f...rom leather, this durable pair will take you from season to season with style! read more

Territory
$44.99

Territory Men's Faux Leather High-Top Round-Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape...: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

Rockport
$130.00

Get the best of modern technology and vintage styling with the Rockport Wynstin Chelsea Boot. Featuring the truTECH® system, this ...ankle boot provides shock absorption at the heel and rebound at the forefoot for excellent comfort. Also, a removable... read more

Territory
$44.99

Territory Men's Faux Leather High-Top Round-Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape...: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

Dr. Scholl's Original Collection
$124.95

The Dr. Scholl's Original Collection Credence Chelsea Boot is sleek and rugged, with twin gore for an easy fit. A clean silhouette... and modern styling make this boot an everyday staple. Twin gore Memory Foam Cool Fit insole Stitch welting Crepe-like... read more

Territory
$44.99

Territory Men's Faux Leather High-Top Round-Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape...: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

John Varvatos
$798.00 $359.02

JOHN VARVATOSModel: Fleetwood ChelseaModel #: F2046P2Color: (001) BlackMaterials: Upper: LeatherLining: LeatherOutersole: RubberRe...tail: $798 read more

Territory
$44.99

Territory Men's Faux Leather High-Top Round-Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape...: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

Territory
$49.99

The high-top Chelsea dress boot by Territory have premium faux leather uppers that rise to the ankles with subtle top-stitching bo...rdering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. This boot is available... read more

Territory
$44.99

Territory Men's Faux Leather High-Top Round-Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape...: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

Territory
$44.99

The high-top Chelsea dress boot by Territory have premium faux leather uppers that rise to the ankles with subtle top-stitching bo...rdering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. read more

Territory
$44.99

Territory Men's Faux Leather High-Top Round-Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape...: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

J'aime Aldo
$44.99

A Modern Twist To The Classic Chelsea Design! Stretch Ankle with Full Side Zip Closure!Full Side Zip ClosureStretch Elastic Ankle ...for ComfortRubber Sole, Squared ToePadded InsoleDesigner Inspired read more

Lucky Brand
$119.95

The Lucky Brand Men's Hutchins Chelsea Boot has pitch-perfect construction that makes it comfortable enough for everyday wear. Wit...h genuine leather uppers in heritage styling, it looks great with every ensemble. Twin gore Lug sole Mixed material upper. read more

Territory
$44.99

Territory Men's Faux Leather High-Top Round-Toe Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leatherToe shape...: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: mediumLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

Ariat
$129.95 $96.95

The Ariat Midtown Rambler Chelsea Boot is a lightweight and comfortable companion for your casual outings. This ankle boot is desi...gned with ATS® technology that cushions and supports your foot as you move, ensuring good posture and reducing fatigue so... read more

Territory
$49.99

Territory Men's Faux Leather High-Top Round-Toe Wide-Width Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leath...erToe shape: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: wideLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

ECCO
$230.00 $126.97

The classic ECCO Turn GORE-TEX® Chelsea Boot gives you the best of comfort and style, all year round. A textile lining along and r...emovable, leather-covered inlay sole with ECCO Comfort Fibre System™ ensure a healthy inner environment. This boot is also... read more

Territory
$49.99

Territory Men's Faux Leather High-Top Round-Toe Wide-Width Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leath...erToe shape: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: wideLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

Dunham
$165.00 $65.97

The Graham-DUN shoe is sure to add a dash of class to your formal ensembles. This classic shoe features an Ortholite footbed that ...enables a lightweight and comfortable all-day wear. Featuring a moisture-wicking Dri-Lex lining, this shoe is breathable... read more

Territory
$49.99

Territory Men's Faux Leather High-Top Round-Toe Wide-Width Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leath...erToe shape: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: wideLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

Danner
$139.95 $113.95

Get cracking at work wearing the Danner Lookout Station Office 5.5" Chelsea Boot. This boot features an anatomical design and broa...der toe box for a more responsive fit, and an Airthotic® heel clip for support. The patent-pending, dual-density footbed... read more

Territory
$49.99

Territory Men's Faux Leather High-Top Round-Toe Wide-Width Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leath...erToe shape: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: wideLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

Ariat
$129.95 $96.95

The Ariat Midtown Rambler Chelsea Boot is a lightweight and comfortable companion for your casual outings. This ankle boot is desi...gned with ATS® technology that cushions and supports your foot as you move, ensuring good posture and reducing fatigue so... read more

Territory
$49.99

Territory Men's Faux Leather High-Top Round-Toe Wide-Width Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leath...erToe shape: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: wideLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

Danner
$139.95 $113.95

Get cracking at work wearing the Danner Lookout Station Office 5.5" Chelsea Boot. This boot features an anatomical design and broa...der toe box for a more responsive fit, and an Airthotic® heel clip for support. The patent-pending, dual-density footbed... read more

Territory
$49.99

Territory Men's Faux Leather High-Top Round-Toe Wide-Width Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leath...erToe shape: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: wideLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

SM New York
$60.00 $40.50

Show off your aptitude for style with the men's Talent Chelsea boot from SM New York. Classically styled with a 3-inch shaft and g...ore paneling at the outer ankle, this footwear goes mod with the addition of a zip closure along the inside ankle.... read more

Territory
$49.99

Territory Men's Faux Leather High-Top Round-Toe Wide-Width Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leath...erToe shape: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: wideLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

Structure
$70.00 $47.25

Rock a hip retro image with the classic design of the men's Fitz Chelsea boot by Structure . Rising to the ankle, this casual boot... sports a smooth leather upper that's accented at the heel by a decorative patch of textured rubber. Dual elastic gore... read more

Territory
$49.99

Territory Men's Faux Leather High-Top Round-Toe Wide-Width Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leath...erToe shape: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: wideLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

Covington
$60.00 $40.50

Dress to Impress with the Covington Men’s Cicero 5 Chelsea Black Boot You’ll look dapper with these Men’s Chelsea Black Boots givi...ng your outfit a boost. Featuring a polished, sleek look, these shoes are a smart choice for the office. A versatile... read more

Territory
$49.99

Territory Men's Faux Leather High-Top Round-Toe Wide-Width Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leath...erToe shape: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: wideLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

J'aime Aldo
$79.00 $44.99

A modern twist to the classic chelsea design! Stretch Ankle with Full Side Zip Closure! Visit www.zenzoshoes.com for more styles!E...asy On/Off Full Side ZipStretch Elastic Ankle for ComfortRubber Sole, Squared ToePadded InsoleDesigner Inspired read more

Territory
$49.99

Territory Men's Faux Leather High-Top Round-Toe Wide-Width Chelsea Dress Boots: Height: ankleStyle: dress bootMaterial: faux leath...erToe shape: roundHeel height/type: 1.3" blockPlatform height: 0.35" platformShaft height: 4.5"Circumference: 10"Width: wideLining: no liningSole material: man-madeFootbed: paddedUpper/outsole material: faux leather/man-madeAll measurements are approximate and may vary by size read more

Territory
$44.22

The high-top Chelsea dress boot by Territory have premium faux leather uppers that rise to the ankles with subtle top-stitching bo...rdering the stretchy side panels. Mahogany faux woodgrain block heels and outsoles finish the look. read more

Clarks
$169.95

Say yes to impeccable casual styling with the Clarks Clarkdale Gobi Chelsea Boot. Part of the Clarks® Artisan Collection, this boo...t provides excellent arch support, and features a removable polyurethane footbed. Part of the Clarks® Artisan Collection... read more

Alpine Swiss
$97.50 $34.99

"FREE SHIPPINGNash Chelsea BootsBy Alpine Swiss We've elevated the classic Chelsea Boot style with our new Nash Chelsea Boots. The... snakeskin texture upper is unique and effortlessly stylish. The timeless silhouette is versatile enough for your formal... read more

Clarks
$169.95

Say yes to impeccable casual styling with the Clarks Clarkdale Gobi Chelsea Boot. Part of the Clarks® Artisan Collection, this boo...t provides excellent arch support, and features a removable polyurethane footbed. Part of the Clarks® Artisan Collection... read more

Alpine Swiss
$97.50 $34.99

"FREE SHIPPINGNash Chelsea BootsBy Alpine Swiss We've elevated the classic Chelsea Boot style with our new Nash Chelsea Boots. The... snakeskin texture upper is unique and effortlessly stylish. The timeless silhouette is versatile enough for your formal... read more

Rockport
$130.00 $64.97

Get the best of modern technology and vintage styling with the Rockport Wynstin Chelsea Boot. Featuring the truTECH® system, this ...ankle boot provides shock absorption at the heel and rebound at the forefoot for excellent comfort. Also, a removable... read more