The Best Men’s Henley Shirts to Buy Right Now

There aren’t all that many style essentials that we think look great on every guy, but one of the best men’s henley shirts is absolutely one of them. Worn by style legends of the past and the present, favored for rugged style situations, grueling activities and even more leisurely pursuits, the henley is, quite simply, one of the coolest shirts a guy can own. That’s just a fact, so be sure to read up on why we love a henley shirt, and why you need to add one to your arsenal alongside other tried-and-true staples (be it a classic Oxford shirt or one of the best wool T-shirts).

The henley is the rare type of shirt you can wear just about anywhere, with the exception of a black tie dinner, an ultra-formal meeting or a seriously buttoned-up office. Don’t believe us? Just try one of our favorite picks (more on that in a second) and see for yourself. But why do you need one of the best new henleys, and why now? To understand the rugged utility and timeless style of the henley shirt, it’s worth going back in time just a bit to the garment’s humble origins.

The henley shirt functions in much the same way today, and although it’s been ages since henley shirts were first worn

The henley shirt was first worn all the way across the pond in Great Britain, and specifically in Henley-On-Thames, preferred by rowers as a sporting shirt and later, by gentlemen of all sorts as an undershirt. The button placket, usually three or four buttons these days, helped the collar keep its shape beneath a starched shirt, and when worn on its own, it offered ventilation or added warmth depending on how the buttons were used.

The henley shirt functions in much the same way today, and although it’s been ages since henley shirts were first worn, the style is still popular, and worn pretty much everywhere stylish, dependable clothes are trusted. the best men’s henley shirts provide just the right dose of utilitarian style and performance-minded design.

Henley shirts are made out of a wide variety of fabrics, too — there’s something to suit every preference, and that’s the case no matter if you prefer moisture-wicking merino wool, insulating thermal stitching or something else. If you’ve already got a rotation of long-sleeve crewneck shirts though, why do you need a henley shirt? It all dates back to when the buttons of the henley shirt served that noble purpose for rowers. You can still use the buttons of a henley to ventilate your upper half, and those buttons also look much more visually interesting than a crewneck collar.

It’s sort of like the difference between wearing a plain white T-shirt and a T-shirt with a pocket. One of the best pocket tees, for instance, is just ever so slightly different from a tee without a pocket, which can look more like an undershirt (although every guy still needs one of the best white T-shirts, to be sure). It’s also akin to wearing one of the best V-neck T-shirts, because it’s the design details, like the collar design, that elevate the henley above your rotation of standard T-shirts. To keep it simple: A well-curated wardrobe needs a henley or two, or three no question about it.

It’s a garment with history, heritage and rugged appeal, plus a spirit of adventure (just think of the famed style aficionados who’ve worn henleys through the years, be it James Bond in No Time To Die or a real-life fashion hero like Ryan Gosling). How to find the best one for you? We’re glad you asked – keep these tips handy to perfect the fine art of wearing a henley.

What to Look for in a Henley for Men

  • Find the right fabric: Like your favorite T-shirt or any other garment worth wearing consistently in your wardrobe, it all comes down to the fabric you’re wearing closest to your skin. As we mentioned, henleys made out of material like merino wool (which is moisture-wicking, anti-microbial and especially useful for performance) are going to serve you differently than a henley made out of, say, soft slub cotton. Henleys made with a thick thermal knit are going to serve as an insulating layer when teamed with a flannel shirt and waxed trucker jacket, for example, while some softer cotton henleys are more suited to be worn casually on their own or underneath a puffer jacket or shirt jacket for style that’s more lightweight and breathable. Any style you choose should suit your own lifestyle and daily needs.
  • Don’t be afraid to invest: Buying one of the best men’s henleys shouldn’t be wildly expensive, nor should it be a style move that leaves you hanging onto a cheap henley. Although they’re a wise purchase in the moment in terms of saving a few extra bucks, the best men’s henley shirts don’t often come from fast-fashion brands. Companies that, instead, offer quality fabrics and construction are worth the higher price tag. We’ll focus on the best men’s henleys as made by reputable companies you can trust across the board. Rugged style has never been more well-made than it is right now.
  • Stock your closet accordingly: The search for one of the best men’s henley shirts is a fun one, yes, but it can be time-consuming if you don’t know where to start (that’s where we come into play). When we talk about finding the right henley, the above factors are important, but let’s take things a step further. We say that if you find a henley you really love, one you can wear constantly and from a brand you trust (and in the right fabric!), well, don’t be afraid to stock up. Find colors that work for you to go along with your preferred style or styles, and before you know it, you’ll have a rotation of shirts to be worn with everything from a blazer to a flannel shirt to a denim jacket. The henley, folks, is just that good.

Now that you’re all squared away and ready to embark on a trek to find the best men’s henleys, well, we’ve got a few ideas of our own in mine to lend a helping hand. Rugged, throwback style with a modern flair is close at hand with the best men’s henleys.

The Best Henleys for Men to Buy Right Now

Flint and Tinder Marled Henley

Flint and Tinder Marled Henley

We already turn to the fine folks at Flint and Tinder (the in-house brand at Huckberry) for a little bit of everything imaginable, from waxed jackets to underwear to T-shirts. This henley is yet another perfect addition to the brand’s truly all-American line of style essentials, made from a heavyweight marled cotton and featuring thick ribbed cuffs and a grey color that goes with everything from blue denim to chore pants. All you need now? Rugged leather boots, which you can also find at Huckberry.

Proof 72-Hour Merino Long-Sleeve Henley

Proof 72-Hour Merino Long-Sleeve Henley

We keep singing the praises of merino, a fabric derived from Merino sheep that’s exploded in popularity in recent years. Merino wool keeps you cool while also insulating when you need it, and the design lends itself to everything from joggers to T-shirts and of course, one of the best men’s henleys. This shirt is also made and sold by Huckberry, so you can be sure it’s up to snuff and gets that crucial seal of rugged, adventure-minded approval.

Vuori Ease Performance Henley

Vuori Ease Performance Henley

You get all sorts of options when shopping for a henley, and that includes henleys meant to deliver plenty of performance and reliable appeal, not unlike henleys worn by old-school rowers. Vuori has updated the time-honored style with fabric that’s distinctly modern however, which means you can wear this moisture-wicking henley with workout shorts to squeeze in a training session, or you can wear it with tailored joggers for laidback lounging. Either way, it’s the right henley shirt for whatever your day holds.

Buck Mason Pima Curved Hem Henley

Buck Mason Pima Curved Hem Henley

We simply can’t get enough Buck Mason in our lives and our wardrobes, and we think you’ll tend to agree once you try out one of the best men’s henleys from the famed American retailer. It makes sense that they’d turn the henley into a rugged and modern staple, complete with soft pima cotton and a neat curved-hem design that makes it easy to wear all on its own (preferably with faded Buck Mason jeans, naturally). Buck Mason is the kind of brand to shop when you want to stock up on multiple favorites of any item, this classic henley shirt included.

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Beau is Brooklyn-based style and lifestyle writer. He covers menswear, gear, spirits, craft beer and music. When not writing, Beau can be found shopping for vinyl or sipping on a Brooklyn beer.


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