Men's Chelsea Boots

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Lucky Brand
$119.95

The Lucky Brand Men's Buck Chelsea Boot has pitch-perfect construction that makes it comfortable enough for everyday wear. With ge...nuine leather uppers in heritage styling, it looks great with every ensemble. Twin gore Lug sole Heel pull tab. read more

Naot
$206.00

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

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

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

Deer Stags
$79.95

Look sleek and cool with Deer Stags Award updated Chelsea Boot. Synthetic and leather upper Twin gore paneling for a secure fit.

Nunn Bush
$95.00 $66.95

Spruce up your casual look with aplomb wearing the Nunn Bush Hartley Chelsea Boot. From the Oak Creek Collection, this ankle boot ...features suedetech linings for moisture-wicking, and a hand-burnished upper, which ensures breathability. Dual Comfort technology uses a combination of memory foam, which conforms to your foot, and an open-cell EVA foam that absorbs the pressure, while walking, for all-day comfort. Part of the Oak Creek Collection Dual Comfort footbed Suedetech lining for added comfort Memory foam sockliner for support and comfort Double-gore design Hand-burnished upper for breathability Rubber outsole provides traction. read more

Lucky Brand
$119.95

The Lucky Brand Men's Buck Chelsea Boot has pitch-perfect construction that makes it comfortable enough for everyday wear. With ge...nuine leather uppers in heritage styling, it looks great with every ensemble. Twin gore Lug sole Heel pull tab. read more

Kenneth Cole
$174.99

Kenneth Cole + 37.5 Technology Presents TECHNI-COLE Footwear ? maintain the ideal microclimate comfort system for your foot. Moder...n and understated these Chelsea boots by Kenneth Cole feature smooth polished leather uppers side elastic goring and a low... 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

John Varvatos
$798.00 $359.02

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

Robert Wayne
$134.95

Sleek and stylish, the Robert Wayne Delaware Chelsea Boot features double gore sides for an easy pull-on design. Twin gore Ankle h...eight. read more

Alpine Swiss
$115.00 $44.99

"FREE SHIPPINGMen's Sion Chelsea Boots By Alpine SwissMSRP $115.00Product Features:Lightweight & breathableShaft measures 4.5" Hee...l 1.5"Elastic side panels for a comfortable secure fitFaux leather or suede upperGenuine suede lining & insoles makes... read more

Dunham
$165.00 $111.95

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

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

Timberland
$160.00 $94.95

The rugged and handsome Timberland Britton Hill Chelsea Boot has an Lags Silver-rated tannery leather upper that's water and stain... resistant. Pair these with your favorite pair of jeans for a stylish look. SensorFlex™ technology ensures all-day... read more

Steve Madden
$109.99

Subtle details like broguing and a brown to tan ombre finish sets these Chelsea boots by Steve Madden apart. A cushioned insole pr...ovides all day comfort. read more

Steve Madden
$140.00 $98.00

Rugged and handsome, the Steve Madden Loren Chelsea Boot features slouch detailing with buckle ornamentation. Soft leather upper D...ouble gore panels for a secure fit Man-made outsole. read more

Joseph Abboud
$129.99

In soft suede these Chelsea boots by Joseph Abboud complement your casual wear with comfort and uncomplicated style. This easy-goi...ng slip-on has an ankle tab side elastic goring and a smooth plain toe. read more

OluKai
$200.00

The Makaloa brings a modern sensibility to the classic Chelsea boot. Elastic gore panel Broguing details.

Lucky Brand
$159.99

A combination smooth leather and suede upper with a buckle detail adds style and flair to this Chelsea boot by Lucky Brand. A soft... cushioned insole provides hours of comfortable wear. read more

Dr. Martens
$110.00 $99.95

The Rivet Steel Toe Chelsea Boot is an excellent general purpose, easy access pull on industrial boot that provides reliable all d...ay comfort. Air cushioned PVC rubber outsole Steel safety toe conforms to and exceeds ASTM standards The sole is cemented... read more

Lucky Brand
$159.99

A soft suede and smooth leather upper with a plain toe and elastic side gorings make this modern Chelsea boot and ideal choice. Pa...ir its uncomplicated style with jeans or chinos for all-day style and comfort. read more

Rockport
$130.00 $110.50

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

Lucky Brand
$159.99

A combination smooth leather and suede upper with a buckle detail adds style and flair to this Chelsea boot by Lucky Brand. A soft... cushioned insole provides hours of comfortable wear. read more

Rockport
$130.00 $129.95

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

Joseph Abboud
$139.99

Understated and stylish this casual Chelsea boot from Joseph Abboud has a smooth plain toe and a soft genuine leather upper with l...eather lining. Elastic gussets at the ankle and a pull tab make for easy and comfortable wear. read more

Skechers
$105.00 $91.45

Get right into the correct style and comfort for the season with the SKECHERS Relaxed Fit®: Molton - Gaveno Chelsea Boot. Slip on ...casual comfort ankle height chelsea boot with stitching and overlay accents. Air Cooled Memory Foam insole. Smooth leather... read more

Todd Welsh
$109.99

With a smooth polished faux leather upper these stylish dress boots will become a go-to favorite. This slip-on style features elas...tic goring on the sides brogued details and a lugged rubber outsole. read more

Dr. Martens
$110.00 $99.95

The Rivet Steel Toe Chelsea Boot is an excellent general purpose, easy access pull on industrial boot that provides reliable all d...ay comfort. Air cushioned PVC rubber outsole Steel safety toe conforms to and exceeds ASTM standards The sole is cemented... read more

Joseph Abboud
$139.99

Understated and stylish this casual Chelsea boot from Joseph Abboud has a smooth plain toe and a soft genuine leather upper with l...eather lining. Elastic gussets at the ankle and a pull tab make for easy and comfortable wear. read more

Dr. Martens
$145.00 $84.95

Take the simply-designed Wilde Chelsea boot, which is cut one inch shorter than tradition allows, and finished in smooth, burnisha...ble leather on top of Dr. Martens' signature air-cushioned sole. Chelsea Boot styling Goodyear-welt construction Oil and... read more

Todd Welsh
$109.99

With a smooth polished faux leather upper these stylish dress boots will become a go-to favorite. This slip-on style features elas...tic goring on the sides brogued details and a lugged rubber outsole. read more

Crevo
$89.95

Keep things cool and comfortable with the stylish Denham Chelsea Boot. Featuring a classic silhouette that rises ankle fashionable... and functional pull-on tabs and an easy gore opening, these British-inspired boots are ideal for trend-setting men who... read more

Joseph Abboud
$129.99

In soft suede these Chelsea boots by Joseph Abboud complement your casual wear with comfort and uncomplicated style. This easy-goi...ng slip-on has an ankle tab side elastic goring and a smooth plain toe. read more

G.H. Bass & Co.
$150.00 $119.99

With durable construction and easy on and off wear, the G.H. Bass & Co. Hendrick Chelsea Boot is the perfect addition to your ense...mble. Chelsea boot Stacked heel. read more

Deer Stags
$64.99

Every man needs one pair of really great boots in his life, and with the Deer Stags Tribeca, we have you covered. Both trendy and ...classic, this Chelsea style boot is multi-purpose, taking you from a day at the office to a night out on the town. Easy... read more

PUMA
$130.00 $97.50

Featuring a water-resistant upper, the lightweight and weatherized PUMA IGNITE Limitless Boot takes its cues from classic boot sty...ling with its hiking-inspired lacing system and Chelsea boot-inspired gore collar. In true PUMA fashion, the bold PUMA... 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

Dockers
$90.00 $69.99

Slide into the sophisticated yet casual Dockers Stanwell Plain Toe Chelsea Boot for an easygoing look. Built with Comfort Zone Tec...hnology and NEVERWET, these slip-on boots feature a dual-zone footbed with cushioned EVA in the forepart for an extra... read more

Hudson London
$122.49

Finish off your look with this sleek and classic boot. The H by Hudson Men's Tonti Suede Chelsea Boot features a suede upper, leat...her lining, a rubber outsole and elastic gore at sides. read more

Dockers
$100.00 $79.99

Keep it classy with the Dockers Ashford Plain Toe Chelsea Boot. These dress boots sport handcrafted details and comfort zone techn...ology for a clean cut style. Comfort Zone Technology Handcrafted details Twin gore panels Stacked heel. Comfort Zone... read more

Dunham By New Balance
$164.95 $89.95

These Mens Dunham By New Balance Graham Chelsea Boots are guaranteed authentic. They?re crafted with Leather/Man Made, and the clo...sure is Pull On. read more

Mauri
$1049.95

The Mauri Annibale Chelsea Boot will add a refined touch to your look. Featuring twin gore panels, this boot is ideal for any occa...sion. Twin gore panels Stacked heel. 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

Danner
$149.95

Step over the huddles at work wearing the Danner Lookout Station Office 5.5" NMT Chelsea Boot. The patent-pending, dual-density fo...otbed offers cushioning and underfoot air circulation. This boot features an anatomical design and broader toe box for a... 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

Dockers
$90.00 $69.99

Slide into the sophisticated yet casual Dockers Stanwell Plain Toe Chelsea Boot for an easygoing look. Built with Comfort Zone Tec...hnology and NEVERWET, these slip-on boots feature a dual-zone footbed with cushioned EVA in the forepart for an extra... 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

Steve Madden
$79.95

The Saine Chelsea Boot from Steve Madden has a suede upper with elastic gore and contrasting rubber sole. Suede upper Elastic gore... Rubber sole. 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

Dr. Martens
$145.00 $109.95

The Chelsea boot takes a well-established silhouette and modifies it though a more refined welt, tapered last, and low profile sol...e. Understated refinement. This is a Goodyear welted product. read more