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The Chelsea boot is a shoe that’s effortless, comfortable and polished. It’s the kind of shoe that never completely leaves the fashion space but instead evolves and changes with the times. Chelsea boots can be dressed up or dressed down, made with fancy and high-quality leather or done up in a rubberized and waterproof outer. They can be sleek, chunky or expertly minimalist. They can be one of your go-to winter boots or something you wear all summer long. Wear them as work boots; wear them as wedding boots. The options are endless.
Whichever way your style leans, you can find a Chelsea boot to match the same kind of feel. “The Chelsea boot is a versatile classic style that comes in all different shapes and fabrications,” says fashion and celebrity stylist Sam Spector. “For example, there are slim, narrow and low-heeled options that will go great with a slim leg and chunkier heel or lug soled pairs that are best with a wide leg.”
Chelsea boots continue to trend in men’s fashion, especially in the fall and winter seasons, thanks to their easy to slip-on design and sleek construction.
What are Chelsea boots?
With roots in England, the Chelsea boot dates back to the 19th century when royal cordwainer, cobbler J. Sparkes-Hall, created a boot with elasticated sides for Queen Victoria. While originally dubbed “the paddock boot” the silhouette became noteworthy thanks to its slip-on construction and sturdy sole.
Fast forward to the 1950s and ’60s and a similar style of boot was worn in the trendy district of Chelsea in London. Young British adults and teenagers began to be spotted in the style, and it was dubbed the “Chelsea boot.” The style became synonymous with the mod scene in the U.K. — a youth subculture inspired by modernism — and eventually took the rest of the world by storm. British bands such as The Beatles, The Rolling Stones and The Who adopted the stylish footwear option, giving the Chelsea boot an avenue to enter the mainstream.
The English boot’s versatility and practicality keep it a perennial favorite footwear option. Over time, countless brands from Blundstone to Calvin Klein have adopted the shape, making the classic style their very own.
The different types of Chelsea Boots
- Suede: This is one of the most common materials for Chelsea boots. Look for sand or brown colors for something you can wear during the warmer months.
- Leather: Leather is a little more durable, if you’re looking for something that can take on tougher weather. Some high-quality and patent leather options are good for dressing up.
- Waterproof: A waterproof Chelsea boot will indeed change your life. It keeps your feet from getting soaked while still being sleek enough to complement the rest of your outfit.
- Lug-soled: Dramatic lug soles on Chelsea boots have been a very popular design element this season, with designers like Prada leading the charge. Lean into the look with something a little chunkier than you’re used to.
Chelsea boots outfits ideas for men
The polished boot has a minimal shape, easy-to-put-on construction and sleek silhouette — all of which make the shoe fun to play around with. They’re perfect to pair with straight-leg jeans of any kind — whether they’re distressed, blue, black or gray. Prince Harry likes wearing Chelsea boots with chinos and a blazer, which is a solid option for anyone heading back into an office. You can also pair a chunky Blundstone boot with workwear pants or chinos for something casual, says Spector. Chelsea boots that are more narrow — maybe in a shinier black or dark brown finish — are easier to wear with a suit or dressier pants (just look to Jaden Smith for inspiration). Spector also likes pairing high-shine, polished boots with velvet and other formal fabrics.
Keep scrolling to shop the 22 best Chelsea boots for men, below.
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Top Chelsea Boots for Men
- Best Outdoor Style: Blundstone 1911 Chelsea Boots
- The Classic: Dr. Martens Chelsea Boots
- Best Casual: Clarkdale Gobi Chelsea Boots
- Best Lightweight Cheslea Boots: Koio Chelsea Boots
- Best Chelsea Rain Boots: Hunter Boots Original Play Chelsea Boots
- Most Comfortable Chelsea Boots: Ugg Biltmore Waterproof Chelsea Boots
- Florsheim Field Gore Boots
- Best Water-Resistant: To Boot New York Hemingway Chelsea Boots
- Best for the Office: Thursday Boots Co. Cavalier Chelsea Boots
- Best Suede Chelsea Boots: Clarks Originals Mileno Chelsea Boots
- Common Projects Winter Chelsea Boots
- Best Designer: Alexander McQueen Leather Chelsea Boots
- Cole Haan Warner Waterproof Chelsea Boots
- Timberland Port Union Chelsea Boots
- Best Brown Leather Chelsea Boots: R.M. Williams Comfort Turnout Boots
- Vince Bonham Water Repellent Chelsea Boots
- Best Chunky Chelsea Boots: Good Man Brand Modern City Chelsea Boots
- Best Affordable Chelsea Boots: Aldo Alencia Chelsea Boots
- Best Brown Chelsea Boots: AllSaints Melos Chelsea Boots
- Sorel Waterproof Chelsea Boots
- Also Consider Best Designer: Saint Laurent Wyatt Chelsea Boots
- Ted Baker London Akeeno Chelsea Boots
Blundstone 1911 Chelsea Boots
Best Outdoor Style
Spector is a big fan of Blundstone’s Chelsea boots. They’re founded in function, meant to be an outdoor shoe that can withstand hard surfaces, rough weather and long-term wear. These are made with a soft, cushioned insole and shock-absorbing lug sole that minimizes impact with every step. The utilitarian pair can be worn for a casual hike or while out on the town. Plus, the two pull tabs in the front and back makes them easy to pull on and take off.
Dr. Martens Chelsea Boots
The Classic
You’d be hard-pressed to find anything more classic than Dr. Martens’ Chelsea boot. It’s a customer favorite, featuring a sturdy leather upper, signature chunky rubber lug sole and signature pull tab. Docs notably take a few wears to break in, but they mold to your foot in the process. The leather is tough but will become soft with time, and the airy footbed is perfectly gentle on the feet. With over 1,200 four and five star reviews, users note that you should size down, as Dr. Martens tend to run on the larger side.
Clarkdale Gobi Chelsea Boots
Best Casual
Comfortable and classic, these brown suede Clarks Clarkdale Chelsea boots are a very solid option for more casual wear. They’re exactly the kind of boots that look great with denim or with chinos. They’re not as chunky as some of the other options on our list but still have plenty of arch support and a molded footbed for all-day comfort. The outer is 100% suede and 100% wearable.
Koio Chelsea Boots
Best Lightweight Chelsea Boots
The brand’s first foray into boots, Koio’s Chelsea boot maintains the high-quality, minimalist construction of its beloved leather sneakers. This silhouette is simple — complete with a suede upper, lugged sole, elastic paneling and pull tab — but is the kind of simple that feels purposeful. It looks especially good with dark jeans, simple T-shirts and bomber jackets.
“It’s become my go-to Chelsea boot for it’s extremely lightweight feel and rugged look,” says Adam Mansuroglu, Director of Commerce. “Koio’s mastery of lightweight-yet-durable construction makes their Chelsea boots an ideal choice for all-weather footwear. Through snow, rain, and sunshine, these simply stunning boots continue to look and feel just as good as they did from the first wear.”
Hunter Boots Original Play Chelsea Boots
Best Chelsea Rain Boots
It’s great to have a lower pair of waterproof Chelsea boots on hand that will keep you dry but cool in the spring and summer. These Hunter Boots Original Play boots are the perfect solution and the pinnacle of reliable rain boots. You just can’t beat Hunter’s foolproof rubber fabric that keeps out wetness during all seasons.
Ugg Biltmore Waterproof Chelsea Boots
Most Comfortable Chelsea Boots
Ugg’s Biltmore waterproof Chelsea boot is one of the many Ugg styles you shouldn’t overlook while boot shopping. Ugg is known for offering comfort, even with its shoes that don’t have a fluffy shearling lining. These are made with a stretchy suede that molds to the shape of your foot. You’ll get full orthopedic-level arch support with Ugg’s signature eNRGY Comfort System footbed. Plus, the full-grain leather outer is completely waterproof.
Florsheim Field Gore Boots
The Florsheim Field Gore boot leans less polished and more work-ready. Available in leather or suede, it features a classic rounded toe and rubberized lug sole to help with traction and keep your feet comfortable all day long. At under $100, these an easy addition to any footwear collection that could use something a little more rugged in it.
To Boot New York Hemingway Chelsea Boots
Best Water-Resistant Chelsea Boots
To Boot is one of Spector’s go-to brands for versatile, affordable Chelsea boots, and there’s no denying the Hemingway style is, first of all, a very beautiful boot. The rugged yet sleek shoe will elevate your entire footwear collection and looks just as good with jeans as it does with anything tailored. Its grayish-black suede finish will blend with many outfits but perhaps more importantly is water-resistant to keep feet dry in inclement weather.
Thursday Boots Co. Cavalier Chelsea Boots
Best Chelsea Boots for the Office
Thursday Boots Co.’s Cavalier boot is stylish and durable thanks to a weather-safe leather upper, which the brand guarantees will only look better with age. The pair also features a full glove leather interior lining and breathable cork midsole for comfort. To top it off, this shoe has a Goodyear welt construction, making the boot water-resistant and resoleable. The black leather finish makes these as versatile as can be, whether paired with trousers and a button-down for work or jeans, a tee and leather jacket for dinner.
Clarks Originals Mileno Chelsea Boots
Best Suede Chelsea Boots
You can’t go wrong with any Clarks Chelsea boot, but we’re especially drawn to the Mileno style. They’re on the chunkier side, with a slightly thick rubber sole, but not so trendy that they’ll feel out of date any time soon. The suede is a light tan that goes with just about everything you could want. We love these with jeans or chinos for casual lunch dates or for more formal drinks outside during the summer. They’ll elevate any outfit in an instant.
Common Projects Winter Chelsea Boots
Common Projects’ winter Chelsea boots are a great upgrade pick if you’re looking to level up your Chelsea boot collection. These top black Chelsea boots for men on the pricier side, but they come with high quality leather and an expert construction to match. The upper is done in a grainy calf leather with elastic sides and two pull tabs for easy wear. The round toe and small but traction-friendly lug sole create a timeless shape you can wear for years to come.
Alexander McQueen Leather Chelsea Boots
Best Designer Chelsea Boots
Alexander McQueen’s leather Chelsea boots are a good example of the trendy, super-thick lug sole construction that’s popular right now. Here, that sole is made even more dramatic done in a rich brown finish that nicely contrasts against the shoe’s shiny black leather upper. The sleek body makes this Chelsea boot work for dressier occasions, too, including with a suit for a trendy take on a formal ‘fit.
Cole Haan Warner Waterproof Chelsea Boots
Cole Haan’s Warner style is certainly the Chelsea boot to buy if you’re often going into an office or find yourself dressing up regularly. These adopt Cole Haan’s signature dress shoe comfort, making them a relief to wear. The sole is lugged, the footbed is cushioned and the sleek black leather upper is waterproof. They look good with a suit or dark denim and a cool blazer.
Timberland Port Union Chelsea Boots
Timberland’s Port Union Chelsea boot brings all the functionality and durability of your standard Timberland boot into something more compact and easy to wear outside of tough work conditions — although it can get along just fine in those, too. The upper is smooth but the sole is thick and rugged sole to ensure your feet stay planted on the ground and not slipping around on any surfaces.
R.M. Williams Comfort Turnout Boots
Best Brown Leather Chelsea Boots
Spector names R.M. Williams a Chelsea boot expert, calling the brand’s Comfort Turnout style especially crowd-pleasing. It has a brown leather upper and elastic paneling that make it both durable and easy to get on. The construction is a little higher in the heel and a bit pointier in the toe, making the shoe feel less clunky and more streamlined.
Vince Bonham Water Repellent Chelsea Boots
Vince Bonham’s water-repellent Chelsea boot is a very good light suede option that begs to be worn in all seasons, but especially in transitional spring and fall weather. That’s because this boot offers protection against the elements while still being lightweight. The tan color works especially well with light and medium wash denims or with navy trousers. The crepe sole is a little more casual-looking but also comfortable — great for situations where you might find yourself standing quite a bit. Plus, these are water-repellent and look as non-clunky as a water-repellent shoe possibly could.
Good Man Brand Modern City Chelsea Boots
Best Chunky Chelsea Boots
Good Man Brand’s Modern City Chelsea boot is one of our favorite takes on the chunky lug sole trend. It’s thick and a little dramatic but still easy and comfortable to wear, especially with something that’s a little more tailored — like cool trousers or a suit. If you’re dressing down the sleek leather pair down, do it with your coolest denim jacket.
Aldo Alencia Chelsea Boots
Best Affordable Chelsea Boots
Aldo’s Alencia chelsea boot is a solid basic Chelsea boot to have — a great option for a first boot or something that’s just effortlessly versatile. This silhouette is streamlined but has a thicker lugged sole, giving you a mid-weight option. The textured rubber on the sole has a solid amount of traction for walking comfortably. Wear these with jeans on the weekends.
AllSaints Melos Chelsea Boots
Best Brown Chelsea Boots
AllSaints Melos Chelsea boots have that rugged, worn-in feel that AllSaints styles are known for. This Chelsea boot has a slightly higher cut, giving it some modern edge. These look good with basically everything, but especially with trendy sweaters, hoodies and jackets. You can lean into the undone feel with a pair of distressed denim or you juxtapose it with a more tailored pant.
Sorel Waterproof Chelsea Boots
Sorel’s waterproof Chelsea boots are lifesaving, and we recommend everyone have a pair on hand for bad weather. The outer part of this Chelsea boot is made of a waterproof cowhide suede, which makes it feel a little less like you’re wearing a full-on rain boot. The sole has a little bit of height to it, which is great for ensuring your feet stay up and out of puddles. Lean into the more outdoorsy feel of the brown-on-brown look of these by wearing them with workwear pants or joggers.
Saint Laurent Wyatt Chelsea Boots
Also Consider Best Designer
Saint Laurent’s Chelsea boots are one of Spector’s favorites for designer boots, and the Wyatt Chelsea boot is an absolute no-brainer for a high-end option. It has a little height in the heel — a look Harry Styles and Jared Leto notably love to wear — making this boot feel all the more streamlined. A slightly pointed adds to their polished effect.
Ted Baker London Akeeno Chelsea Boots
Ted Baker’s Akeeno chelsea boots belong with a suit. The cut is much higher on these than it is on most traditional Chelsea boot styles, giving these a slightly more elevated look. They have a sleek fit on the foot and chunkier sole that makes them feel right on trend.
The best socks to wear with Chelsea boots
We’re big believers in never overlooking your socks, and you better believe that a new pair of boots and a bad pair of socks are a surefire way to get blisters all over your heels. The higher fit of Chelsea boots all but guarantees a low sock will fall down inside them, which can cause rubbing and irritation, says Dr. Raphael Lilker, DPM and owner of the Foot Doctor of New York. Depending on the height of the boot you get, opt for a sock that hits above your ankle bone but not above the ankle of the shoe. Something soft and quarter-length will keep your feet blister-free and your style on point.
Meet the Experts
Sam Spector is a veteran fashion and celebrity stylist who’s worked on editorials for Esquire, Teen Vogue, Men’s Fitness and Interview Magazine and dressed A-list men including Neil Patrick Harris, Ryan Seacrest and Daniel Radcliffe, among others. Also the former fashion editor at Out Magazine, he has a breadth of styling and apparel knowledge, including in the best men’s Chelsea boots.
Dr. Raphael Lilker is a podiatrist and owner of the Foot Doctor of New York, where he specializes in minimal incision surgery for bunion, hammertoes, neuromas, heel surgery for plantar fasciitis and tendon or ligament injuries. His company also creates custom orthotics and Birkenstock sandals for patients with specific needs.
