On Point: 20 Best Men’s Chelsea Boots For Sophisticated Style

By: Shawn | Last Updated: March 2, 2017

The Chelsea boot has evolved into one of the most popular footwear trends to date. Originally designed as a riding boot for Queen Victoria nearly 200 years ago (source); this no-nonsense boot exploded into popularity during the 60’s thanks to the pioneering style of the Beatles.

Over the past few years, Chelsea boots have become the go-to boot for stylish men and women everywhere.

Their chic look and androgynous vibe make it clear that the Chelsea boot is here to stay.

We figured the least we can do is help all you style conscious men out there find the perfect Chelsea boot for all of your city slickin’ needs—wether you’re a Chelsea boot aficionado looking to add a new pair to your already extensive collection, or a newbie who wants to give your shoe arsenal a much needed pick me up—we’ve gone ahead and compiled a list of the best Chelsea boots for men.

If Chelsea boots aren’t your fancy – a more casual Chukka boot can also make for a great addition to any wardrobe.

20 Best Chelsea Boots For Men

Aldo Men's Delano Chelsea Boot

Aldo Men’s Delano Chelsea Boot

Aldo’s stylish designs and reasonable price points have taken the contemporary shoe world by storm.

The Delano Chelsea boot is a great example of why this brand is so appealing. These lightweight leather boots are ideal for both Spring and Fall due to their breathability.

The tastefully rounded toe, elastic inserts, and back loop are all great—albeit, classic—features of these boots. Available in shiny black and smooth cognac, this boot walks the line of casual and cool with ease.

Bruno MARC BERGEN-05 Men's Classic Wing-tip Perforated Leather Lining Chelsea Ankle Boots

Bruno MARC BERGEN-05

Bruno Marc New York serves up their version of the Chelsea boot with some much-welcomed deviations from the classic style.

Comprised from premium faux-leather, this boot is sure to appeal to men who want some serious mileage in the style department. The wingtip detailing gives these contemporary boots a vintage feel. Dress them up or down for an understated elegance.

There’s a very good chance you won’t want to take them off thanks to their cushioned latex footbed and durable rubber sole.

Dockers Men's Badger Chelsea Boot

Dockers Men’s Badger Chelsea Boot

Over the years, Dockers has become a respected name in casual apparel and footwear.

The ‘Badger’ Chelsea boot has got loads of old-school charm with all the added bonuses of contemporary design. The burnished full-grain leather and clean lines make this pair of boots ideal for casual everyday wear.

The flexible construction and cushioned latex footbed are sure to provide exceptional comfort. Finished with vintage-inspired details like contrast stitching and a stacked heel, you’ll be ready to take on the day and dance through the night.

Suede Chelsea Boots

Suede Chelsea Boots – Brooks Brothers

Anyone looking for a classy boot to add to their closet should virtually make their way on over to Brooks Brothers and grab a pair of Suede Chelsea boots.

These guys rarely miss a beat when it comes to crafting quality shoes. Their take on the Chelsea boot is made from a buttery brown suede and leather soles.

Complete with tonal stitching and a perfectly rounded toe, these are the ultimate statement boots! Whether you’re roaming through city streets or headed on a fall vacation with your sweetheart—these top-rated Chelsea boots will definitely not disappoint.

Did we mention they’re imported from Italy? Enough said.

Edward Green Newmarket Chelsea Boots

Edward Green Newmarket Chelsea Boots

The famed British shoemaker Edward Green has been partnering with Brooks Brothers for over 50 years.

Luckily, they’ve joined forces again to bring us the Chelsea boot of all Chelsea boots. The quality of Edward Green’s Newmarket Chelsea boot is nothing short of impeccable.

These antique dyed Calfskin boots are handcrafted in Northampton, England from the finest hand-cut full-grain leather. Every pair is Goodyear welted to ensure the utmost level of durability and longevity.

Before they leave the workshop, these baby’s are hand-polished into a rich, burnished finish that will only get better with age.

O'KEEFFE - Polished-Leather Chelsea Boots

O’KEEFFE – Polished-Leather Chelsea Boots

The masterful Italian artisans at O’Keeffe’s have bestowed upon us a one-of-a-kind Chelsea boot. These polished leather boots embody the ultimate in rugged sophistication.

Every pair is cut from a burnished espresso leather and set on a sturdy heel and well-crafted sole. Details like the sleek side zippers get these boots on fast—perfect for men on the go.

Paired with a slim cut trouser and your favorite button down and you’ve got a versatile look that can transition effortlessly from day to night.

O'KEEFFE - Bristol Oiled-Suede Chelsea Boots

O’KEEFFE – Bristol Oiled-Suede Chelsea Boots

Whenever I’m looking to add some color variance to my closet, a bold pair of shoes is usually my method of choice.

O’Keeffe’s Bristol Oiled-Suede Chelsea Boots come in a tastefully smokey grey that’ll have you looking like you just got off work at the coal mine—the wall street equivalent of a coal mine that is.

Their unique color and sleek silhouette make these top-quality Chelsea boots a stylish pick if you’re looking for a welcomed change from the usually black or brown. Made in Italy from Goodyear welted soles, these boots are sure to keep you lookin’ spiffy for many years to come.

BITFLEX CHELSEA – STONE

Bitflex Chelsea – Astorflex

For all the eco-friendly gents out there who make sustainable fashion a priority, it’s your lucky day! The Bitflex Chelsea boot is everything you’re been looking for and so much more.

Handcrafted by master shoemakers in Northern Italy, these guys have been making killer shoes for over 6 generations. I think it safe to say that these guys know what they’re doing.

These boots are made from premium European leather that is aged to perfection for 30 days. They are then softened into a supple suede and mounted on a 100% natural rubber sole for the perfect balance of style and comfort.

ROSKILDE CHELSEA

Roskilde Chelsea – Duckfeet

It would seem that Europe is eons ahead of everyone else when it comes to craftsmanship and design. The Danish shoe company Duckfeet exemplifies this superior construction like the best of ‘em!

With the natural shape of a foot in mind, their Rockslide Chelsea boot was built for exceptional comfort. Every boot is made from eco-friendly Terrace leather that is handcrafted in Germany.

Complete with the traditional elastic side inserts, this rugged take on the traditional Chelsea boot will keep you roaming through the wilderness is style. Set on a crepe rubber sole and complete with double natural stitching, these are a fantastic pick for anyone looking for both strength and detail.

KENSINGTON CHELSEA BOOT

Kensington Chelsea Boot – Crosby Square

The Kensington Chelsea boot by the luxury shoe label Crosby Square may be just the pick-me-up you needed.

Originally trademarked in 1932, the founders of Crosby Square were thought to represent the epitome of high-quality American footwear in the first half of the 20th century. Their unwavering commitment to style and wearability is evident in the smart and sophisticated design of the Kensington boot.

This nod to the classic Chelsea boot has the traditional elastic gores to ensure a customized and snug fit. Made in Spain with a Goodyear welt, these shoes remind us of the classic details that give Chelsea boots their original appeal.

TAMPER CHELSEA

Tamper Chelsea – Hudson

Despite their humble beginnings, Hudson has grown into an internationally renowned producer of quality both men’s and women’s shoes. Drawing upon stylistic influences from across the globe—weather you’re strolling down a quaint alley in Milan or caught in the hustle and bustle of New York City—they’ve surely got a shoe that will appeal to even the most refined of men.

The ‘Tamper’ is their refreshing take on the quintessential Chelsea boot. Its clean, uncluttered design is complemented by smooth leather and tonal elastic panels. They also feature a practical front and back loop to get them on with ease. Finished with a rubber outer sole for durability, there’s no reason these bad boys shouldn’t be the newest addition to your closet.

Warren Waterproof Chelsea

Warren Waterproof Chelsea – Cole Haan

Anyone who’s ever been caught in a torrential down poor knows that these unexpected showers can be the death of your favorite leather shoes.

Thankfully, Cole Haan’s Warren Waterproof Chelsea is just what you need to carry you through the rainy season. These flawlessly crafted boots are sure to be a practical addition to any man’s shoe arsenal.

The Warren Collection was designed using cutting edge technology to reduce weight while adding flexibility and comfort. They’ve also upped the ante with a sole that offers superior traction in an agile yet stable package.

Grantland Waterproof Chelsea

Grantland Waterproof Chelsea – Cole Haan

If you’re committed to the idea of adding a waterproof boot to your closet with a less “sleek” and more “rough and tumble” vibe, then Cole Haan’s Grantland Chelsea boot has got your back.

These waterproof boots are crafted from rich oil-tanned leather and mounted on a solid recessed lug sole for the ultimate traction on bad weather days. Designed using the same technology as the Warren boot, these guys strike an impressive balance between comfort, durability, and wearability.

Williams Welt Chelsea

Williams Welt Chelsea – Cole Haan

It looks like the design team down at Cole Haan has done it again with the Williams Welt Chelsea boot!

These top-rated Chelsea boots are comprised of high-quality suede and leather uppers as well as a heavy-duty leather storm welt. Let’s just say that it sounds like these boots are made to last. The cushioned footbed and leather sock lining are sure to keep even the burliest of feet happy.

GLOBALWIN Mens 1638 Chelsea Boots

GLOBALWIN Mens 1638 Chelsea Boots

If leather products aren’t your thing, but you’d still like to find the perfect ankle boot—Globalwin’s Chelsea boot may very well be for you. This low-cut ankle boot packs quite the punch and comes in four versatile colors—brown, grey, tan, and black.

The two-eyelet lace-up design and elastic stretch panels allow for easy on/off. Complete with a cushioned footbed for added comfort and contrast stitching for added style, it’s hard to go wrong with this fashionable boot.

 

Steve Madden Men's Hibrid Chelsea Boot

Steve Madden Men’s Hibrid Chelsea Boot

Since its inception in 1990, Steve Madden has been at the forefront of the shoe industry from day one.

Praised for his undeniable ability to transform high fashion trends into wearable footwear for every occasion; the Hibird Chelsea boot speaks to all of the progressive thinking we’ve come to know and love.

The hallmark of this handsome boot is most definitely the toe shape—not quite round and not quite square looks like it’s the perfect place to be! The result is an elegant boot with a European flare.

Sperry Top-Sider Flex Deck Chelsea

Sperry Top-Sider Flex Deck Chelsea

Sperry’s Top-Sider Flex Deck is a Chelsea boot like you’ve never seen it before.

More akin to a rain boot, these babies will be sure to keep you dry and comfortable. Whether you’re caught in the rain or spending a day near the sea, you can rest assured due to their durable and 100% waterproof exterior.

The cozy micro-fleece lining and supremely cushioned footbed will keep you comfortable from above and below. As if that wasn’t enough, the uniquely patterned sole provides amazing traction on both wet and dry surfaces—a necessity for every outdoorsy fellow.

Wolverine Garrick Chelsea Boot

Wolverine Garrick Chelsea Boot

If you’re looking for an understated Chelsea boot that oozes casual luxury then do yourself a favor and slip your feet in the Wolverine Garrick Chelsea boot.

Where do I even begin with these beauties?

I should be mentioned that these highly-reviewed Chelsea boots bring to mind an effortless masculinity reminiscent of the Marlboro Man. The rich color of the pebbled leather has a perfectly aged look and can be easily dressed up or down. If comfort is a must have, then you’ll be sure to appreciate the thick cushioned foot bed—not to mention the micro-suede lining! A durable rubber outsole provides stellar traction for wet weather making these a perfect choice for the cooler months.

Massimo Matteo Chelsea Wing Boot

Massimo Matteo Chelsea Wing Boot

Is ‘dapper’ your middle name?

Well thanks to Massimo Matteo’s Chelsea Wing boot, it is now!

Crafted in Brazil from premium leather, you’ll want to reach for these all year long. The tasteful wingtip design adds a dash of pizzazz to an otherwise straightforward design. The traditional elastic side panels make for a snug fit and the soft leather lining adds a welcomed boost in comfort. Available in black, tan, and a suave reddish-brown; slipping on an awesome pair of boots has never been easier!

Guess Men's Jibbs Chelsea Boot

Guess Men’s Jibbs Chelsea Boot

For all the guys who love to stay on top of the trends, the Guess Jibb’s Chelsea boot will get you exactly where you want to be.

Since the early 80’s, Guess has been a highly sought after name in both men’s and women’s fashion. In recent years, they’ve really hit the nail on the head when it comes to their footwear. The ‘Jibb’s’ boot is no exception!

This suede boot features the usual slip-on design complete with a classic logo plaque. Planning a weekend getaway? Well, the good news is these are the only pair of shoes you need to bring!

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