Elevate Your Fall Footwear With These 17 Stylish Chelsea Boots

men's chelsea boots featured image
Courtesy of Thursday Boot Co.
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Over the last few years, Chelsea boots have risen significantly in popularity in the men’s shoe department—and for good reason. The extremely versatile men’s boot just looks good on its own and pairs well with nearly every single outfit you can imagine. Whether you’re rocking a cozy sweater and jeans look for fall or need a semi-formal shoe to rock at a work function — the Chelsea boot is there for you. Plus, they tend to be built durably and can handle the elements throughout fall and winter, so your feet will stay warm, dry and stylish at the same time.

After the creation of the Chelsea boot in 1851, it went on to be considered the British equivalent of a cowboy boot, and then gained a second life thanks to a little indie rock band called the Beatles.

The boots are still the same now as they were then: made of lighter materials, an elastic center, and a pull tab that makes it so the boots slip on and off with ease. Whether it’s full suede, leather, or rubber, we’ve rounded up 17 of our favorite Chelsea boots on the market. Whether you’re a leather fanatic, a classic dresser or someone who loves to make a statement — there’s a Chelsea boot in this list that will fit your fancy. 


1. Thursday Boot Company Duke Chelsea Boots


Thursday Boot Company is one of those direct-to-consumer brands that’s gained considerable popularity in recent years — but don’t let fancy Instagram ads get to you, as they’re capable of making extremely quality products. Their take on a Chelsea-style boot, known as the Duke, is our pick for the best Chelsea boot around. The moldable footbed contours to your foot over time, the suede itself is water-resistant (should you get caught in the rain) and the footbed has plenty of good traction to it. While we like the versatility of the Dark Olive suede, there are plenty of other colors if you want to change it up — just know this is the boot you should consider first when thinking about getting a Chelsea boot.


Thursday boot company Duke Men's Chelsea boot, best Chelsea boot overall Courtesy of Amazon


2. find. Men’s Chelsea Boot


If you’re totally unsure as to whether or not Chelsea boots are for you, consider this option from the brand find. as it’s under $50. The hybrid look of a Chelsea upper and a sneaker bottom combine for a great blend of both casual and formal. The brown suede version is enough of a neutral too that it will pair exceedingly well with a lot of other clothing options, which means you’ll certainly get great use out of it.

find. Men's Chelsea Boot light brown Amazon


3. Clarks Clarkdale Gobi Dark Brown Suede


A lot of Chelsea boots on this list are suede options, but one of the most luxurious options is this Clarkdale option from Clarks. The rich, coffee-colored suede is a great companion to both lighter and darker outfit hues. The full-grain leather sock liner provides both comfort as well as a smart look. Additionally, the rubber sole gives all-day cushion so you can go straight from the office to date night with ease. And if you’re the kind of person that needs to slot in your own inserts, you can do that with these.

Clarks Clarkdale Gobi Dark Brown Suede Clarks


4. Aldo Relari Chelsea Boots


You don’t need to drop a significant amount of cash to get a high-quality, attractive pair of Chelsea boots. Aldo makes excellent affordable options that retain all of the simple, minimalist ankle boot features you want from this specific style. These Relari boots feature a suede exterior, a round toe and a rubber sole that’ll last you through the seasons with proper care. These boots are easy to wear with any outfit and simple in their design, a major plus. The navy color is a bright, fun move if you’re looking to spice things up — but they also come in black and beige if you want something a bit more classic.

aldo navy chelsea boot Courtesy of Aldo


5. George Cleverley Morris Suede Chelsea Boots


These unique Chelsea boots have been refined by George Cleverley’s English workshop and its craftsmen for years. The buckle in the front is a nice touch over the beautiful brown suede color, and the boot has leather linings inside that will mould to the unique shape of your foot. The soles are also tipped with rubber for stability. The makers also recommend investing in a special brush that removes dirt, scuffs and other marks after each use.


George Cleverley chelsea boots Courtesy of Mr. Porter


6. Dr. Martens Chelsea Boot


Relevant now just as much now as they were back in the 1980s, the Doc Martens silhouette has been a classic style shoe that’s just as beloved by punks as it is by fashionistas. The rugged, rubber sole is instantly recognizable, giving a slight military-inspired vibe to whatever other clothing you pair alongside them. Plus, as a Chelsea-style boot, they’re easy to take on and off and durable enough to wear time and time and time again.

doc martens black Chelsea boot Courtesy of Amazon

7. Taft The Dylan Boot in Woven


This woven Chelsea boot is one of the most unique designs we’ve seen. The beautiful exterior will stand out without making an outlandish footwear statement, and the ankle strap and buckle across the top adds an additional style element to the look. The Jodhpur boot has a sleek silhouette that’s hand-woven in Spain and Burnished with stain and a heating element for a stunning color and finish. The weave is Blake-stitched on top of the leather sole for a durable, comfortable and sleek look that will last you for years. It’ll go great with darker jeans or even a khaki pant in warmer weather.

taft woven brown chelsea boot Courtesy of Taft


8. Hunter Original Waterproof Chelsea Boot


If you love the style and shape of a Chelsea boot but want something that you can wear in the rain without having to worry about ruining it, Hunter’s “Original” Chelsea boot can withstand all kinds of nasty weather. With a strong rubber sole that provides plenty of traction and grip, you won’t slip and slide while walking along. While it’s great to wear as a commuting shoe on those days in which there’s a torrential downpour, they work just as well in the sun for those looking to play with textures in their outfit.

hunter rain chelsea boots Courtesy of Nordstrom


9. Blundstone Chelsea Boot


Decidedly workwear in their look and structure, Blundstones are a rough and tough pair of boots. Expertly made to look to look as utilitarian as possible, Blundstones are chunky — but in a stylish way. Originating from Australia, they’re seemingly a distant cousin of something like Red Wings or other similar heritage boots. The smokey black color is also a nice change of pace from your typical black leather boot. 


Blundstone men's chelsea boot, chelsea boots Courtesy of Amazon


10. Mr P. Heath Shearling-Lined Leather Boots


This stylish take on a winter Chelsea boot from Mr. Porter is definitely a great pick for colder weather if you’ve got a solid chunk of change to spend. Mr P’s are stylish and functional, two attributes you don’t commonly see in one pair of shoes, making them that much more worth the price tag. The intense lace-up design gives a nod to classic hiking boots. They’re handmade in Northampton, England with black leather lined with shearling for additional warmth. The soles are also slip-resistant for icy walks, so you can strut confidently in great-looking boots without worry of a wipe-out.

Mr P leather black chelsea boots Courtesy of Mr. Porter


11. R.M. Williams Yard Boot 365


These chunky, fun, pop-of-color Yard Boots from R.M. Williams are a modern take on the classic Chelsea design and are “built for thinkers, tinkers and creators.” They’ve got a modern, thick sole and heel and come in a few different suede varieties including this quartz color. R.M. Williams’ designer, Marc Newson, pays homage to the brand’s first hard-working and hard-wearing boot of the 1950’s, with the addition of a playful rubber outsole. The elastic gussets that line the boot have an interwoven tug that assists with foot entry, and the addition of Poron padding on top of the full-leather sock lining makes them extra comfortable.


R.M. Williams Yard Boot, light beige Chelsea boot Courtesy of R.M. Williams


12. Frye Men’s Seth Chelsea Boot


Frye’s Seth Chelsea boot is the first leather option on this list, which is fitting given the fact that the brand is well known for its quality craftsmanship when it comes to leather. Unique in its design because of the dip-dye leather, these boots are then burnished by hand in order to give further richness. Offering a rich texture, the leather will get better as it ages and as you wear the boot more.

Frye men's black chelsea boot, chelsea boots Courtesy of Amazon



13. Common Projects Suede Chelsea Boots


Essentially a luxury version of the New Republic Chelsea boots, Common Projects has built a name for themselves around making the best versions of men’s basics. What the shoe lacks in any sort of overt or flashy design features, it makes up for in superior quality and construction (they’re handmade in Italy to ensure to the finest levels of craftsmanship). Incredibly soft to the touch and light wash in their color, they’re a stunning looking pair of boots that will elevate any outfit.

common projects suede beige chelsea boots Courtesy of Mr. Porter


14. AMIRI Suede Chelsea Boots


Okay, these are a serious splurge — but if luxury is the name of your game then we recommend these AMIRI boots from Mr. Porter. The slim, accentuating shape is lifted up by a substantial Cuban heel that’ll boost your height without sacrificing comfort. They’re made in Italy with high-quality brown suede and have elasticated sides that make them easy to put on and take off. The pointy toes and the bright color are evocative of Mr. Mike Amiri’s youth— defined by rock n’ roll culture in California – a cool vibe to emulate if you ask us.

AMIRI Suede beige chelsea boots Courtesy of Mr. Porter


15. R.M. Williams Craftsman Leather Chelsea Boots


Another great R.M. Williams option, this leather Craftsman boot is made by some of the best Australia has to offer, and it shows. The company’s head of production, Mr. Michael Williams, has been with the company since he was an apprentice 40 years ago, and says these boots are his favorite. The block heels give a little lift and, according to Williams, once “you break in a ‘Craftsman’ and the leather then starts forming to your foot, I find them so comfortable.” Take it from him folks, and grab yourself a pair. If you want leather, there’s no better pair.


R.M. Williams Craftsman Leather black chelsea boots Courtesy of R.M. Williams


16. Thursday Boot Company Legend Black Matte Boots


There’s something about matte that’s just so… sophisticated and classy. While getting matte paint on your car seems a bit ridiculous, these black matte Chelsea boots definitely don’t. The black matte surface on the outside comes from their Rugged and Resilient leather that has a Goodyear Welt Construction for durability. These boots also have cork-bed midsoles that form to your feet the more you wear them for comfort. They’re handcrafted and built for men who wear their boots out until they’re on their last leg, so there’s no need to treat them gently.

Thursday Boot Company black matte men's boots Courtesy of Thursday Boot Co.


17. Alexander McQueen Platform Chelsea Boot


If you’ve already got a few really solid Chelsea boots or are looking to add something really adventurous to your lineup, this platform Chelsea boot from Alexander McQueen is worth buying. The chunky sole is of a similar style to recent, popular sneakers but on a shoe that would be totally acceptable in an office environment. Meanwhile, the red stitching and elastic center add even more character to a boot that’s already not lacking in panache. It’s a bold choice for a bold man, but we think you might be up to the challenge.

Alexander McQueen Platform Black Chelsea Boot Nordstrom