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The Chelsea boot is one of those items of footwear that’s never truly gone out of style since its inception, way back in the Victorian era. Sure, they’ve been more popular at some times than others—they were a core part of the look of London’s Swinging 60s scene—but you could wear them in pretty much any decade and feel good about it. We’ve rounded up our current favorites, so put down those tennis shoes and check out the best Chelsea boots for men.
Our top picks for the best Chelsea boots for men
Best customizable Chelsea boots: R.M. Williams Comfort Craftsman Boot
Leather boots can be quite the investment, so you want to be sure you’re getting exactly what you want. Dimitry Loiseau, founder and chief editor of REGARD magazine, advises checking out R.M. Williams’ Comfort Craftsman pair of Chelsea boots, since there’s not only four colors to choose from (black, and three distinct shades of brown), you can also choose from three different widths—narrow, regular, and wide.
Specifications:
- Sizes: 2-18, with half sizes
- Fabric: Leather, with rubber sole
- Colors: Black, dark tan, chestnut, rum
- Price on publish: $539
What we like:
- Lots of options for finding the exact right pair.
- Handcrafted from a single piece of yearling leather.
What we don’t like:
- Expensive.
The bottom line:
A classic-looking boot, with enough customization options to give you a modern shopping experience.
R.M. Williams Comfort Craftsman Boot
Best value Chelsea boots: Hunter Refined Chelsea Boot
Did we mention that these boots can get expensive? If you want the flash shoes without the cash blues, try Hunter’s great-looking pair. “It’s rare for a quality Chelsea boot to come in lower than $200,” says Roger LaGrone, founder of Alexander Noel. “This one is durable, waterproof and vegan.” They may be made from natural rubber, rather than leather, but you’ll be glad of that when the weather turns wet and soggy.
Specifications:
- Sizes: 7-13
- Fabric: Natural rubber
- Colors: Black
- Price on publish: $155
What we like:
- Inexpensive for Chelsea boots.
- Waterproof.
What we don’t like:
- Not leather.
- A small number of customer reviews claim they run a little large.
The bottom line:
An all-rubber alternative to the traditionally leather boot, with a lower price tag to match.
Hunter Boots | Men's Refined Slim Fit Chelsea Boots 13 Black
Best waterproof Chelsea boots: Cole Haan Warner Waterproof Chelsea Boot
As a certain cartoon pig is so fond of saying, “If you jump in muddy puddles, you must wear your boots!” You might not necessarily want to get these boots covered in mud, but rest assured that if you do get the urge to go for a splash, your feet will stay dry throughout. Recommended by Loiseau, they’ve also got traction-enhancing lug soles, so you won’t be slipping over in those puddles, either. Overall, these are a comfortable and sturdy alternative to men’s walking shoes for winter.
Specifications:
- Sizes: 7-13 (half sizes up to 11.5)
- Fabric: Leather and textile upper, rubber sole
- Colors: Black
- Price on publish: $220
What we like:
- Sturdy.
- Waterproof.
- Comfortable foam insole.
What we don’t like:
- Only one color option.
The bottom line:
A solidly constructed and comfortable boot that will take the worst the weather can throw at it.
Cole Haan Women's Warner Grand Waterproof Chelsea Boot, Black, 10.5
Best luxury Chelsea boots: Magnanni Leather Chelsea Boot
Despite being our luxury pick, these aren’t the most expensive boots on this list, but they’re not cheap, either. LaGrone, however, believes you get what you pay for, saying, “Magnanni is known for its quality and craftsmanship, yet this boot is still reasonably priced. It features a rubber sole and leather shell, alongside all the classic features of a Chelsea boot.” They certainly do look luxurious, it must be said, especially the deep, rich cognac version.
Specifications:
- Sizes: 7-13, with half sizes
- Fabric: Leather, with rubber sole
- Colors: Black, cognac
- Price on publish: $398
What we like:
- Beautifully crafted boot.
- Made from water-resistant Italian calfskin.
What we don’t like:
- Runs large–recommended to order a size down.
- Expensive.
The bottom line:
An elegant and attractive boot, with all the subtle attention to detail you’d expect from a high end brand.
Magnanni Leather Chelsea Boot
Most versatile Chelsea boots: Blundstone Dress #063
If you’re spending a couple hundred bucks on boots, you ideally want a pair that can be worn with multiple different types of outfits. For that, LaGrone suggests trying Blundstone’s Dress #063, which he describes as, “Durable yet chic.” The boot—available in four pleasingly distinct colors—is sleek and simple enough to work with a smart-casual outfit, but could easily be dressed down with jeans and a sweater (or hoodie).
Specifications:
- Sizes: 4-13 (half sizes up to 11.5)
- Fabric: Leather, with TPU outsole
- Colors: Stout brown, black, rustic brown, rustic black
- Price on publish: $214.95
What we like:
- All four colors are attractive.
- On the lower end for price.
What we don’t like:
- A minority of customer reviews complain that they’re a little tight and narrow in the toes.
The bottom line:
A Chelsea boot that would look good with virtually any outfit, with four distinct colors to choose from.
Men's Dress Chelsea Boots, Black #063
Best Chelsea boots for wide feet: R.M. Williams Gardener Boot
Chelsea boots probably aren’t the first choice of footwear for the wider-footed gentleman, but they can work if you choose the right pair. Loiseau recommends R.M. Williams’ Gardener Boot, which is available in either its regular form, or a more accommodating wide version. Crafted from a single piece of oiled kip leather and featuring a sturdy rubber sole, they’ll be more than up to a spot of gardening, too.
Specifications:
- Sizes: 2-16, with half sizes
- Fabric: Leather, with rubber sole
- Colors: Black, brown
- Price on publish: $539
What we like:
- Durable.
- Comfortable.
What we don’t like:
- Expensive.
The bottom line:
A pricey but meticulously-crafted boot, suitable for those with wider-than-average feet.
R.M. Williams Gardener Boot
Best chunky Chelsea boots: Common Projects Chelsea Boot
Chelsea boots tend to be on the slimmer side, especially compared to the more oversized boot options out there, like Doctor Martens or Caterpillar. If you want a chunky Chelsea, though, Loiseau suggests Common Projects’ offering, which maintains the classic sleek shape of the upper, but sits it atop a gratifyingly beefy sole. If you’re not sure whether you’re feeling like a punk or a mod, your feet, at least, can sit somewhere in between.
Specifications:
- Sizes: 7-14
- Fabric: Leather, with rubber sole
- Colors: Dark brown, black
- Price on publish: $672
What we like:
- Unique look.
- Beautiful grained leather.
What we don’t like:
- Very expensive.
The bottom line:
A stunning–but also stunningly expensive–piece of footwear that combines the elegance of a Chelsea boot with the heft of a work boot.
Common Projects Chelsea Boot in Dark Brown at Nordstrom, Size 11Us
Best work Chelsea boots: Blundstone Lug #2238
This suggestion very much depends on the kind of work you’re doing—digging ditches in a pair of boots that costs over $200 seems inadvisable, at best—but if you refuse to sacrifice your style on the job, these are durable enough to keep up, at least. “This chunky boot is great for working in unpredictable conditions,” says LaGrone. “It has a grooved sole to help prevent slipping and is made from waterproof leather.”
Specifications:
- Sizes: 4-14 (half sizes up to 11.5)
- Fabric: Water-resistant leather, with rubber sole
- Colors: Black, rustic brown, rustic black
- Price on publish: $234.95
What we like:
- Tough.
- Slip-resistant lug sole.
- Steel shank.
- Shock-absorbing heels.
What we don’t like:
- A small number of customer reviews say they run a little large.
The bottom line:
A sturdy, no-nonsense boot designed to keep your feet safe and dry.
Common Projects Chelsea Boot in Dark Brown at Nordstrom, Size 12Us
What to consider when buying Chelsea boots for men
There are various factors to keep in mind when purchasing Chelsea boots, and Loiseau says to pay special attention to the following:
Material
High-quality materials, Loiseau explains, are vital in order to guarantee long-term durability and comfort. “Chelsea boots that are made of premium leather exude sophistication and age beautifully over time,” he says. “I encourage ethically sourced leather or vegan alternatives, which reflect values of sustainability.”
Price
Boots can be expensive, but if it’s a pair you’re going to wear for years, it may well be worth the initial investment. “Research brands offering exceptional craftsmanship without breaking your budget,” Loiseau suggests. “Investing in well-made pairs will save you money in the long run because they will last you longer!”
Function
Obviously, you’re going to want to think about where you’ll be wearing your boots—are you looking for a pair for formal occasions, casual nights out, or both? Loiseau points out that the boot’s sole, grip, and overall construction all need to be equally considered when making your selection.
How we selected the best Chelsea boots for men
We chose our entries here by following the advice of our trusted experts, who have years of experience in the world of shoes and men’s clothing brands more generally. We also ensured that each of our entries was highly rated by customers, only including those with positive reviews, touting comfort, fit, look, and durability.
What is the best color for Chelsea boots?
“When it comes to fashion choice, color is one of the most subjective elements,” says LaGrone. “For shoes, men tend to veer on the safe side, sticking to dark neutrals that can match everyday attire. Most people have the least amount of shoes compared to other clothing pieces in their wardrobes, so it makes sense they want them to be as cross-functional as possible. However, given the leather construction of Chelsea boots, there are many colors available, and the elastic banding on the ankle provides the option to add an accent color. Glossy blacks and browns, suede medium browns, and deep burgundies are all very popular and classic colors for a Chelsea style.”
What are the different types of Chelsea boots?
“The Chelsea boot has a long history, dating back to the 18th century, and its style has changed a lot since,” says LaGrone. “The basic premise of the Chelsea boot is that it’s a boot that can be easily slipped on without the need for laces or buckles. For this reason, it also quickly gained popularity.”
“All Chelsea boots are ankle boots, characterized by the elastic band and ankle pull tabs,” continues LaGrone. “As established, they can vary in material, with the most common men's styles featuring leather. But other types would be rubber, exotic skins, patina finish, shell cordovan, suede, and various fabric materials. Other characteristics may include having heeled, platform or chunky-sole Chelsea boots, however, these are most commonly seen in women's fashion. For men's fashion, most of the variation will be in the toe design, whether it is pointed, rounded or squared, and whether or not it features a wingtip design. Any styles that begin to veer away from the elastic band and ankle tab styles would be classified as just ankle boots, and not a type of Chelsea boot.”
Below, Loiseau breaks down a few common styles of Chelsea boots, and how to recognize them:
Classic Chelsea Boots
“These boots boast an elegant silhouette, with elastic side panels for ease of on/off wear as well as a rear pull tab, providing quick on/off. Known for their timeless appeal.”
Brogue Chelsea Boots
“These boots feature elaborate brogue details, like perforations or wingtips, that add sophistication and character to their classic Chelsea design.”
Suede Chelsea Boots
“Crafted of soft suede rather than leather, these Chelsea boots provide a casual and relaxed aesthetic, perfect for creating stylish yet laid-back looks.”
Chelsea Boots with Rubber Soles
“While traditional Chelsea boots feature leather soles, rubber-soled ones provide enhanced traction and durability, making them suitable for various weather conditions.”
Frequently asked questions (FAQs)
What are the best brands for Chelsea boots for men?
Loiseau has a few recommendations, as follows:
Grenson
“This iconic British brand is known for their expert craftsmanship and commitment to ethically sourcing leather products, offering classic and modern Chelsea boot options.”
R.M. Williams
“R.M. Williams of Australia is well known for making boots crafted with superior materials that combine sustainability with ethical production methods, to provide long lasting shoes and boots. They prioritize sustainable practices for production to guarantee product durability for years.”
Common Projects
“This luxury minimalist brand prides themselves on using clean lines and premium materials in their Chelsea boot designs, meticulously hand-crafted, often featuring subtle yet distinctive gold serial number branding.”
Thursday Boot Company
“Offering fashionable Chelsea boots made of ethically-sourced materials at an excellent value-for-money price point, Thursday Boot Company stands out with stylish yet cost-effective footwear solutions that meet both affordability and craftsmanship criteria.”
Are Chelsea boots still in style?
“Chelsea boots are absolutely still in style,” confirms LaGrone. “Both the traditional style and reworked, trendier options are loved by the shoe community.”
What kind of pants should I wear with Chelsea boots?
“Chelsea boots look most flattering when paired with a tapered ankle slack,” says LaGrone. “Of course, for work-boot styles and function, denim pants will often also be paired with Chelsea boots.”
Are Chelsea boots considered formal wear?
“Certain Chelsea boots can certainly be dressed up for more formal occasions such as dinner parties and business events,” says LaGrone. “However, the Oxford loafer remains the most common formal shoe for men's fashion [see our guide to the best loafers for men for more]. If you’re looking for a more formal Chelsea boot, I recommend opting for a glossy leather finish.”
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