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 and fall, 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 14 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.
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 to find something decent.
To be completely honest, it’s unlikely that you’ll find a fantastic pair of well-made resolable Chealseas for under 100 bucks. At this pricepoint, I’d definitely consider getting a pair of factory seconds, or a lightly used pair from online or a thrift store.
With that said, here are a few of our favorites that ring in at under $100:
Bruno Marc Suede Chelsea
Bruno Marc’s versatile Chelsea boot is an all-around great option, especially when you consider it’s only about $55.
You can choose from 9 colors, which is quite the variety at this price range. A breathable suede upper delivers a classic look while the EVA foam footbed keeps your feet comfortable.
If you’re after a casual suede boot for less than $100, the Bruno Marc is a fantastic pick.
Amazon Essentials Men’s Chelsea
Amazon Essentials is a cheap, no-nonsense brand, but there are some surprisingly decent pieces in the lineup.
The Essentials Chelsea is one of the better clothing items. It’s 100% synthetic, but the material is pretty high-quality for the price, and the color has a nice richness to it.
Realistically, these aren’t made for wearing all day long throughout winter. These are best for the guy who only needs to pull out a pair of Chelseas on certain occasions. But for that use case, these Essentials make a lot of sense.
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.
New Republic Sonoma 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.
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.
Clarks Clarkdale Gobi Chelsea Boot
Clarks is an immediately recognizable name in the world of footwear, so it shouldn’t come as a shock that the brand makes some excellent Chelseas.
The company’s Clarkdale Gobi Chelsea offers the same premium build quality you’d expect from a Clarks shoe. The boot is available in both suede and leather options, which is a nice plus, and the range of colors has something for everyone.
Blundstone BL550 Classic 550 Chelsea Boot
For many people, the name Blundstone is synonymous with Chelsea boots. The brand’s unique design elevates the traditional Chelsea look.
While Blundstone has a sizable catalog, it’s hard to go wrong with the Classic 550 Chelseas. These boots feature Blundstone’s typical design, complete with the double loops, and a subtle bit of asymmetrical stitching as a finishing touch.
You have plenty of color options (17 as of this writing!) and a good range of sizes to choose from. Keep in mind that Blundstone uses Australian sizing, so if you’re in the US, you’ll need to convert your foot size to AU.
Check out our review of the Blundtone Classic 550 if you want to learn more.
Best Men’s Chelsea Boots $200 and Up
Want a more luxurious Chelsea boot made of the finest materials? Here are our top picks for boots that cost $200 and up.
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 the slim, more formal silhouette of dress shoes like Oxfords 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
Oliver Cabell’s design philosophy is simple: the brand makes timeless shoes for men. One look at their Chelsea boot makes that apparent. This is a classic Chelsea boot done really well.
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.
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.
Idrese Harvey Chelsea Boot
Idrese is a new-ish direct-to-consumer footwear brand that may not be as well known as some of the major players on this list but is still worth your consideration.
They have a couple of Chelsea boots in stock, but we think their suede, crepe sole Harvey is an excellent choice.
This is a casual Chelsea boot, but it’s not chunky or oversized. The organic crepe sole makes it very comfortable, and the Italian suede feels premium.
The Blake stitch construction makes this boot lightweight without sacrificing longevity, as these Chelsea boots are still reasonable.
If you stamped some gold lettering on the side of these boots, we might be fooled into thinking they were Common Projects…
Speaking of the devil, while 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.
Grant Stone Chelsea
According to some experts, Grant Stone makes Alden-quality boots without the Made-in-USA price tag (they’re manufactured in China instead).
These Goodyear-welted Chelsea boots are sort of a mix of rugged and refined. The dark “earth” Commander leather is definitely rugged, but the shape and sole style make this a slightly more casual boot.
With a leather welt, midsole and insole, and a rubber outsole, these Grant Stone Chelsea boots are pretty much ready for anything.
Koio is probably best known for its Capri sneaker that’s often touted as a Common Projects alternative, but that’s not the only Koio shoe that should be on your radar.
Enter the Koio Trento. This elegant Chelsea features blake-stitched construction and leather certified by the Leather Working Group. Like all Koio shoes, the Trento is made by hand in Italy.
Considering the Trento’s specs, it’s pretty impressive that these boots can be found for under $300. If you’re after a Chelsea that balances design and durability, this could be the one.
Astorflex Bitflex Chelsea Boot
This Huckberry exclusive is a hidden gem that offers a ton of premium features at a startlingly affordable price.
The Astorflex Bitflex is handmade in northern Italy using beeswax nubuck leather and 100% natural crepe soles. Since the boots are hand-finished, there’s natural color variation, meaning each pair is unique.
Another element that stands out is the tapered, asymmetrical goring that gives the boot a nice balanced profile. It’s a nice bit of flair that makes the Bitflex stand out from the rest.
You can pick up a pair for just $215, which feels like a bargain for what you get. That said, if you’re after the beeswax nubuck, be aware that there’s only one colorway offered (which is the dark chestnut pictured here).
Taft Jude Boot
If you’re familiar with Taft shoes, then you’ve probably seen the brand’s maximalist take on footwear. However, Taft also offers some subtler shoes.
The Jude Boot is one of those subtler options. It’s a minimal Chelsea boot made from Spanish suede using blake construction. The creamy beige tones of both the boot and the goring give the Jude a classy appearance that contrasts nicely with dark trousers.
The only noticeably loud aspect of the Jude is it sole, which features rubber inserts for extra traction. The large dots and half-and-half heel are quite eye-catching, but they also serve a highly practical purpose, and who can argue with that?
Allen Edmonds Liverpool
Allen Edmonds needs no introduction, so we’ll get right to the point: the company’s take on the Chelsea is a characteristically excellent boot.
The Liverpool is one of the most handsome Chelsea boots out there thanks to its graceful silhouette and refined leather upper. You also get bench welt construction and soft cork insoles for a durable, comfortable shoe.
At $495, it’s undoubtedly a luxury choice, though it’s backed by the brand’s highly lauded craftsmanship. This is pretty much an endgame dress boot, so if it’s within your budget, the Liverpool is worth serious consideration.
This Chelsea from Meermin is another great dress boot choice. Between the muted two-tone colorway and the subtle stitching, it’s even more minimal than the average Chelsea.
It’s made from hand-stained Italian suede, and in true Meermin fashion, the sole is Goodyear welted. You can pick from 8 color and material options, so you’re not limited to suede.
Meermin also offers every size from 4.5 to 15, including half sizes, which is fantastic for guys whose feet are smaller or larger than average.
R.M. Williams Comfort Craftsman
If you want to pull out all the stops and treat yourself, then this Chelsea from Australian heritage brand R.M. Williams might fit the bill.
The Comfort Craftsman is the brand’s signature Chelsea silhouette that’s made from a single piece of leather and features a welted non-slip sole. The boot is made by hand from start to finish and is crafted to last.
It bears a hefty $495 price tag, but that figure is admittedly softened a bit by the painstakingly handcrafted construction.
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!