Chelsea boots are timeless and versatile, and almost every guy should have a pair in his collection.
The Chelsea’s sleek silhouette makes for a nice relaxed boot that you can wear nearly year-round. Obviously, they’re ideal for winter, they’re also great shoes for summer if you want a lighter boot to pair with some outfits.
In addition, Chelseas can be dressed up or down with ease. You can wear them with jeans and a jacket for a casual look, or you can dress them up as part of your winter business casual wardrobe. That’s why the Chelsea is one of our favorite business casual shoes for men.
In this article, we’ll look at 13 pairs of Chelseas at various price ranges. If you’re in the market for a pair, then read on for our list of the best men’s Chelsea boots.
Table of Contents
Short on time? Here are our top three picks for the best Chelsea boots you can buy right now:
Read on to see the complete list…
Best Men’s Chelsea Boots Under $100
It’s completely possible to get a nice pair of Chelseas for less than a hundred bucks. Of course, there are a lot of cheaply made shoes out there, so you have to know where to look.
Here are a few of our favorites that ring in at under $100:
#1: Urban Outfitters Dress Chelsea
Urban Outfitters might not be the first brand you think of when you think of Chelsea boots, but they have a pretty appealing option that costs just $89.
Simply called the UO Dress Chelsea, this boot is as no-frills as its name. It’s the traditional Chelsea look we’re all familiar with.
The UO Dress is made from a soft suede and uses rubber for the outsole. It’s available in chocolate (personally, I think it’s more caramelly), olive and tan.
All in all, if you’re pressed for cash, the UO Dress Chelsea isn’t a bad choice.
#2: Dockers Stanwell
Dockers needs no introduction. You already know they make classic workwear-inspired gear, and their Stanwell Chelsea boot is no exception.
This boot is a rugged take on the classic Chelsea silhouette. Think of it as a casual boot that takes inspiration from work boots. The Stanwell uses Dockers’s proprietary Comfort Zone and NeverWet technologies, meaning this boot repels water while keeping your feet nice and comfortable.
The Stanwell also features full grain leather uppers and a multi-cushioned sole. The light stitching seen on the chocolate and dark tan colorways also adds a nice pop of color.
Since this is a more affordable boot, there are a couple of small quality compromises, like using rubber instead of crepe for the outsole. But given that it retails for $90, you’re getting a solid value for the money.
#3: Zara Brown Soft Leather Ankle Boots
Coming in at just under the $100 mark is this pair of Chelseas from fashion giant Zara.
Strangely, Zara doesn’t say that these are Chelseas. For some reason, Zara lumps all of their ankle boots together under one category, so you might not have run into these before if you were just searching for Chelseas.
Like the UO boots, these are simple and to the point Chelseas.
The upper is a blend of leather and elastane to provide a healthy amount of stretch.
These boots are also available in black, and there’s also a brown “athletic” version that features some significant differences, like differently shaped goring and a flatter sole. (Btw, check out this article on black vs. brown boots if you’re having trouble deciding.)
Best Men’s Chelsea Boots From $100-$200
This price range is a real sweet spot for Chelsea boots. This is where you’ll find really well-crafted boots that will last you multiple seasons, but at the same time, their price tags aren’t enormous.
#4: New Republic Harvey Leather Chelsea Boot
New Republic gets a lot of buzz for their affordable boots, and there are good reasons for that. Their Chelseas are surprisingly nice for the price, and they look great to boot (sorry).
New Republic has a few types of Chelsea boots, and many of them are constantly selling out, so they can be hard to find. Thankfully, it seems like the brand’s Harvey boot is readily available via Menlo House.
Featuring a natural crepe outsole, vegetable-tanned leather welt and a padded insole, the Harvey packs a big punch. It’s a minimal, contemporary Chelsea with a touch of stylistic branding on the heel tab. It also has a 100% leather lining, which makes this boot especially soft and breathable.
At $129, the Harvey is a great deal. It’s one of the best men’s leather Chelsea boots you can buy at this price point.
#5: Dr. Martens Felix
If you’re looking for a Chelsea that stands out from the rest, take a look at the Dr. Martens Felix.
This boot takes design cues from rain boots (like galoshes), and its curved broguing that traces the shoe’s shape is a unique touch.
Like most other Doc Martens shoes, its look is somewhere between the military and rock-and-roll styles. As such, it’s more structured (and less sleek) than the other Chelseas on this list.
For this boot, Dr. Martens uses a synthetic material instead of leather. Even though it’s synthetic, the fabric is both soft and durable. The brand’s AirWair Bouncing Soles provide slip resistance and traction, which makes this a great winter boot.
Dr. Martens is well known for its build quality, so for $150, the Felix is a tempting option. This is an ideal boot for guys who want a non-standard Chelsea with a bit of an attitude to it.
#6: Thursday Boots Cavalier
Thursday Boots makes high-quality everyday boots based on classic silhouettes, which is why their Cavalier is arguably one of the best men’s suede Chelsea boots you can buy today.
The Cavalier features weather-resistant suede, Goodyear welt construction, full glove leather lining and an antimicrobial shock-absorbing insole. Even better, they’re handcrafted, so the attention to detail is extreme.
Perhaps the best part is that these boots only cost $190. That’s an impressive price given the quality of the materials and the manufacturing. Think about it: You’re getting handcrafted leather boots for under $200. For this price range, the Cavalier is hard to beat.
Best Men’s Chelsea Boots $200 and Up
Want a more luxury Chelsea boot made of the finest materials? Here are our top picks for boots that cost $200 and up.
#7: Beckett Simonon Bolton
Looking for a suave, refined pair of Chelsea boots? Beckett Simonon’s Boltons might be just what you need.
Slightly taller and more tapered than most Chelseas, the Boltons are more formal than most of the other boots on this list. It evokes shoes like Oxfords and brogues while staying true to the form of the Chelsea boot.
Beckett Simonon is renowned for their meticulous construction, and that’s true of the Boltons as well. The leather is hand-cut, and the soles are hand-sanded, resulting in an artisanal product without the artisanal price.
The Boltons come in at $229, which is quite something considering how well these boots are made. They’re ideal for men who want a dressier boot.
Oliver Cabell Chelsea Boot
This is the shoe you think of when you think of a Chelsea, but there are little touches (like the olive goring) that add subtle flair. Even better, these boots are extremely well made. The upper is Venetian split suede, and the outsole is a custom Italian crepe sole. If that weren’t enough, the shoes are hand-stitched and lasted in Spain.
Surprisingly, these Chelseas are just $238.
#9: Red Wing Shoes Weekender Chelsea
Red Wing is one of the most famous boot brands. Their rugged, heritage-style boots are staples in many guys’ wardrobes. However, their Weekender Chelsea might have flown under your radar.
This relaxed Chelsea is made using stitch down construction for a flexible fit that doesn’t require any break-in time. As the name implies, the Weekender is a more casual boot that prioritizes comfort.
It’s not quite as formal as other boots on this list, but it’s perfect if you don’t need to dress up your Chelseas.
The Weekender will run you $239 and is available in four rustic colors. It’s a solid choice if you’re after a super comfortable Chelsea.
#10: AllSaints Rhett Suede Chelsea Boots
AllSaints is well known for their biker-influenced leather jackets, so it’s no surprise that their Rhett Chelsea boot has a similar vibe.
This black Chelsea boot for men features a textured suede upper, a crepe outsole and the classic Chelsea silhouette you know and love. It fits right into that biker aesthetic, although you could definitely dress it up if you need business casual shoes.
The Rhett is also available in a nice light taupe (with darker, contrasting goring) and a smoky charcoal grey. Of course, black is a classic Chelsea color, but the other tonal options are great if you’re looking for something off the beaten path.
Coming in at $260, the Rhett is a premium product that’s built to last a long time and look good doing it. If the rugged style of AllSaints is your thing, then you’ll want to give these boots some serious consideration.
#11: WANT Les Essentiels Wellington Men’s Leather Chelsea Boots
Montreal-based WANT Les Essentiels is a high-end brand that prioritizes purposeful design. To that end, they’ve reimagined the Chelsea boot in the form of their Wellington.
The Wellington was made with both fashion and function in mind. Notably, it has a much thicker sole for added durability, and the toe features a reinforced mudguard. It’s handcrafted in Portugal using Italian leather, so there’s no doubt this boot will be able to take a beating.
Due to its thicker profile and toe guard, the Wellington has a similar style to Dr. Martens. It’s more rugged than the average Chelsea boot, but it’s not overwhelmingly so, which means you can style it like any other Chelsea.
The Wellington retails for the hefty price of $475, but again, these are handmade shoes built to last. As far as premium Chelsea boots go, the Wellington is a unique, formidable offering that deserves more attention.
#12: Common Projects
Common Projects may be best known for their highly sought-after Achilles
As you’d expect from Common Projects, these boots are minimal and functional yet still extremely stylish. This Italian-made boot features a particularly sleek profile and the brand’s signature foil stamping on the heel.
Although these cost a whopping $515, you’re getting the iconic Common Projects look and quality. You are paying for the name, of course, but these are also really well-made, sleek boots that will hold up to just about anything.
#13: Lavati Chelsea Boot
Ending our list is this premium Chelsea from Italian footwear brand Lavati. These are the most expensive boots on this list at $595, but the attention to detail and build quality is nothing short of luxury.
Handcrafted in Italy, these boots feature waterproof suede, gum trainer soles and an embossed insole. They give off a confident vibe that’s reminiscent of high street brands like Saint Laurent. (These even come with their own travel bag.)
These boots are also really versatile. They can add a touch of swagger to more casual outfits, but when paired with more formal outfits, their sleekness is highlighted. These boots are as close as you’ll get to a perfect Chelsea that goes with everything.
With all of the great options for men’s Chelsea boots out there, it was admittedly pretty difficult to make this list. But you really can’t go wrong with any of these boots. If you’re in the market for Chelseas, definitely consider the boots on this list.
Are you planning on grabbing any of these? Did I miss your favorite Chelsea boots? Comment below with your thoughts!