When you think you’ve got a solid grip on your footwear rotation, perhaps filled with pairs you love to wear, it can be fun – yes, fun! – to throw a little something different in the mix. This is where the Chelsea boot comes into play.
In my experience, Chelsea boots toe the line between rugged and refined based on the style you shop – perhaps that’s why I find myself wearing some form of pull-on Chelsea boots nearly every single day of the week.
While I’m willing to bet you’ve got rugged work boots, classic chukka boots and perhaps some lace-up captoe or wingtip boots, the best men’s Chelsea boots take your footwear collection to another level.
And if you’re like me, it seems there’s never really a bad time to break out some Chelsea boots (except the high heat of summer, when it’s a better bet to wear something like casual loafers). I prefer to step into my Chelsea boots for just about any style situation, be it a rock concert (I favor Blundstone boots) or an evening whiskey bar visit (I opt for a pair with a sleek, dressier silhouette).
Particularly during the fall and winter, Chelsea boots amp things up a bit – they signal refinement and sleek style – the sort of dressy appeal that can be worn with tailored trousers or chinos.
Not every pair of Chelsea boots is as dressy as those black leather FRYE boots I just discussed. In fact, these handsome suede Chelsea boots – made by family-owned Astorflex and sold by rugged style purveyors Huckberry – definitely lean more casual.
It seems you can always leave it to Huckberry to know what its customers want, and in my experience, they tend to knock it out of the park every time.
Huckberry brought the Astorflex brand to even greater prominence, and in my time wearing Astorflex Chelsea boots, it’s a well-deserved honor – durable, dependable, comfortable and utterly classic (yet modern).
It comes down to the springy, soft crepe rubber sole for plenty of comfort and laidback style, along with the all-natural aged leather upper. Team these with your favorite pair of faded jeans and a classic henley to nail a casual, everyday look.
It’s hard to find a better value on the market for Chelsea boots than New Republic’s fan favorite Sonoma Boots. They retail for under $100 when on sale, with some serious style points that make them look like a much more expensive pair of boots.
I can’t help but appreciate the mix of style points, value and comfort for that price tag, and I prefer to wear my Sonoma Suede Boots in a more refined, yet no less versatile fashion with blue jeans or with grey chinos.
The use of tan suede is eye-catching and stylish, especially when paired with deep navy blue jeans or olive chinos, while they sit atop a comfortable crepe rubber sole for all-day comfort.
Blundstone boots are legendary in my book, and if ever you’ve worn these ridiculously dependable pull-on boots to tackle yard work or take on a rugged fall cabin getaway, you know the drill.
I mentioned that I wear mine as often as I possibly can, be that for brewery visits, rock concerts or Brooklyn park strolls. The leather is relatively supple right out of the box, the sole itself absorbs shock and stress for springy comfort, and they look even better with a bit of wear and tear on them (at least, in my experience wearing Blundstone boots).
In fact, I’ve got three pairs currently – and very well might be in the market for a fourth.
The Australian company has made these boots for decades, using tough yet supple leather and a slip-resistant outsole to provide traction and reliable performance seemingly no matter the weather. Get a no-frills black pair and wear them to handle chores – then, clean ‘em up and wear them to a dive bar or rock concert, because they can nearly do it all.
You’ve perhaps spotted plenty of pairs of Western boots out and about these days – all things Western are truly fashionable right now, be it your rugged Western shirt or a Wild West-inspired trucker jacket.
Tecovas has been leading the charge for about a decade now in terms of sharp, affordable Western boots, and the Tecovas Chance Chelsea Boots are a nice change of pace if you don’t want to quite go full-on cowboy in your next #OOTD.
In fact, they’re more dressy and refined than one might expect, with a stacked heel and a clean, sharp silhouette. Rich bovine leather makes the difference, too.
Grenson has been a standard bearer for some of the finest footwear in the world for decades, with impeccable British craftsmanship and design leading the way. Its boots are premium (with a price tag that reflects that approach), but it’s an investment you won’t regret.
The Declan is an elegant boot that calls to mind the Chelsea boots favored by The Beatles, built on the company’s custom elongated last for a dressy finish. The studded rubber sole delivers crucial traction, but it’s the sleek, black leather that elevates these into a suit-ready pair of boots.
The Chelsea boot is a statement-making set of footwear, and that’s certainly true when worn alongside your best navy or charcoal suit.
Beckett Simonon’s Bolton Chelsea Boots are made to rise to the occasion, with Italian leather and an expertly crafted design that’s all about tailored refinement. Specifically, they’ve honed in on a tapered design that makes them supremely well-suited to, yes, dress in your Sunday best through fall and winter.
The latest and greatest from Huckberry’s own Rhodes Footwear blends a few key components: The sleek and easy-to-wear styling potential of a Chelsea boot, plus the rugged dependability of a tough work boot.
They’ve reinforced these boots with roughout leather made to withstand abrasion and get better with age. And for good measure, they sit atop a lightweight outsole that delivers some serious spring in your step. If you want a pair of Chelsea boots to wear with jeans, get this pair ASAP.
Taylor Stitch hits the right balance between road-ready, hard-wearing and yet remarkably stylish with the handsome Ranch Boots. Think of them like a hybrid between a dressy Chelsea boot and a moto boot, with resoleable construction – after years of wear – and heavy-duty elastic detailing.
I’ve been seriously impressed with my pair over the years – they’re rugged and tough as hell, yet the leather isn’t overly stiff out of the box. The design is ultra-sturdy, with a no-slip Vibram mini-lug outsole.
The Saddle Tan leather will also only get better the more you wear this pair as I’ve found over the years. Plus, it’s helpful that they look right at home with navy Taylor Stitch chinos.
Some Chelsea boots are every bit as streamlined and sleek as your go-to dress shoes, and FRYE certainly hits the mark with the Tyler Chelsea Boots.
For starters, the premium black leather upper gives them a bit of rock star sheen, especially when worn with black jeans or even a navy suit (yes, navy and black work well together – James Bond would approve).
The use of rubber in the leather outsole gives them a bit of hard-wearing sturdiness, while the leather-lined footbed will mold to your foot over time.
You can tell pretty quickly, in my experience, when a men’s clothing brand cuts corners in making Chelsea boots. That’s certainly not the case with Adelante, which uses time-honored practices and precise attention to detail in handcrafting these boots in Guatemala.
Each pair is finished by an expert craftsperson using richly designed materials, like full-grain leather and resoleable Goodyear welt construction for long-lasting durability. It’s a difference you can feel, as I’ve had my Adelante boots for years – they’ve certainly only improved with age.
It might seem uncanny to head to Clarks for a pair of Chelsea boots, since the brand is so well-known for its iconic chukka boots. I’ve found Clarks boots to be remarkably comfortable and well-made at every turn though, and if you favor a slightly dressier pair of boots from the well-known British brand, the Clarkdale are a solid step up.
The crepe rubber outsole carries on the brand’s penchant for comfort, while the rich brown suede is a suitably fall-ready material that should team up stylishly with burgundy corduroys, tan chinos or timeless faded blue jeans.
KOIO is best known for its well-crafted approach to sneakers, using rich European leathers and custom designs to turn the sneaker into a pair that’s so cool, it can even be dressed up with a suit (seriously).
Its Trento Boots are another step in the right direction, carrying on the company’s carefully considered approach to footwear.
The toe shape is razor-sharp, the rich suede upper is luxurious, and they’re handmade in Italy for the ultimate in footwear excellence. Plus, the price tag isn’t all that bad considering what you’re getting in each box.
Chelsea boots work well with tailored blue jeans or wool pants and an Oxford shirt for business casual looks. While I’d advise against pairing Chelsea boots with, say, lounge pants, plenty of casual, biz casual and tailored looks will look even better with the right set. The elastic side design makes Chelsea boots easy to pull on and even easier to wear, and materials like suede and rich leather give you options.
For instance, you can pair shades of brown with navy blue chinos or light wash jeans, and common colors like black Chelsea boots wear perfectly with light grey denim, olive chinos or – of course, black jeans. I even style tan Chelsea boots with black, grey or blue denim – or even olive chinos. You can’t hardly go wrong with Chelsea boots, and that’s why I personally can’t get enough of ‘em.
They add a dash of on-trend edge, they signify you mean business and hey, the best Chelsea boots are just downright cool. These are the pairs we’ve got our eyes on right now.