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In the taxonomy of T-shirts, the henley is perhaps the most versatile of the lot. Polos, for instance, have fixed collars that transmits formality almost instantly. On the other end of the spectrum are crewnecks and V-necks, styles that are casual to core. But the henley serves as the happy medium, a topper that meanders between refined and relaxed. It walks that fine line effortlessly. Which is why it has become my go-to on days when I deviate from my uniform of an oversized button-down and want to just chill—but still impart some sense of distinction. 

The henley’s anatomy, the way the style is structured (more of this in a bit), consists of a T-shaped silhouette with a scoop neck that features—and here’s the clincher—a button placket, usually two or three. This design detail gives me the ability to dress it up or down at a moment’s notice. In the office or when the temperatures drop, I keep everything buttoned-up. When the heat rises and happy hour is calling, however, I unfasten it all the way, showing some skin and letting my gold chain necklace shine through. The henley is a style of shirt that is categorically cool. It is effortless. But it didn’t start out that way.


A Brief History of Henley Shirts

The henley was never supposed to be worn on its own—at least not out and about. The style of shirt dates back to late-18th-century England, when it was first used as an undergarment for men. Made from soft cotton, and without the constriction of a collar, it was the first layer of its kind to breathe and move with the body. It wasn’t long until it became the uniform of choice for rowers in the town of Henley-on-Thames, which, since 1839, has hosted the Royal Regatta, the most important rowing race in the world. Eventually, the henley grew to be such an integral part of each tournament that it became a tradition for the losing team to give their shirts to the winners. They literally lost their shirts.

Then, for over a hundred years, the henley was strictly a sporting garment. This was the case until, rumor has it, the 1970s, when American sportswear really gained full steam and a merchandiser from Ralph Lauren reconsidered the henley’s potential. What was once considered underwear, and then simply something to be worn for rowing or workouts, has become a comfortable, cool T-shirt for everyday use.


The Anatomy of Henley Shirts 

Today, the henley is everywhere. It telegraphs the casual ease of a tee, but thanks to its two-, three- or four-button placket, it has just enough design elements to elevate it into something more. Also, the best men’s henleys are no longer just made of cotton; merino wool, moisture-wicking tech fibers and luxurious options such as silk and linen are also available. There are options that you can wear to a party, to run errands, or to lounge at home. While the style has really only been around in its current iteration since the 1970s, it already feels like one of menswear’s most enduring workhorses.


Best Overall Henley

Few brands operate with such obsessive attention to fibers and how they look and feel as Sunspel, so it comes as no surprise that this soft, comfortable henley still has a smart, pulled-together look. And this particular version, made of extra-long Supima cotton and cut to flatter, is as classic as they come. It’s a style that traverses seasons, able to be dressed up or down depending on the scenario on your schedule.

Material: Supima cotton.
Fit: Regular.
Colors Available: 6.


Best Classic Henley Shirt

As we mentioned, the henley’s rise in the menswear pantheon owes a great deal of thanks to Ralph Lauren. No list on the subject is complete with it. The brand constantly offers the style, tweaking it every few years to create pieces that feel both timely and timeless. Prime example: This model, which stays true to the essence of classic henley but is made softer with the use of jersey cotton slub. 

Material: Cotton slub.
Fit: Regular.
Colors Available: 3.


Best Waffle-Knit Henley 

Who can resist the comfortable texture of a waffle knit? This pullover henley, with a traditional round neckline and three-button placket, is made from a waffle knit material that is still lightweight enough to wear in warmer climates.

Material: Cotton and polyester.
Fit: Regular.
Colors Available: 1.


Best Linen Henley

You should 100 percent trust Italian brand 120% when it comes to linen. A White Lotus–style linen muumuu this is not—it’s breathable and soft without sacrificing fit, and it comes with a five-button placket that quietly and elegantly makes a statement.

Material: Linen.
Fit: Regular.
Colors Available: 1.


Best Jersey Henley

Don’t confuse the name of Barena’s luxe Dabon Jersey with the Garden State. It is made of 100 percent cotton and drapes like pure magic. It is also breathable for those sunny Italian afternoons in Capri. And like the best parts of Italian fashion, this henley communicates style and elegance without trying too hard.

Material: Cotton-jersey.
Fit: Slim.
Colors Available: 1.


Best Lightweight Henley 

The name says it all: Todd Snyder’s henley is absolutely lightweight, but not in a way that feels flimsy—the result of the micro-textured cotton slub that has just the right amount of heft and stretch. It can serve as an insulating base layer during the cold months or can be worn on its one when summer arrives. 

Material: Cotton slub.
Fit: Slim.
Colors Available: 1.


Best Luxury Henley

Nobody understands sexy, slinky better than Tom Ford. This long-sleeve henley is exactingly crafted from a truly luxurious stretch-silk satin (there’s a touch of elastane) in a fine gauge knit that hugs in all the right places. Sure, it will cost you, but can you really put a price on luxury? Turns out, you can.

Material: Silk and elastane.
Fit: Slim.
Colors Available: 6.


Best Vintage-Inspired Henley

On the hunt for something with a lived-in look, something that imparts vintage vibes? J.Crew has just the thing. The brand’s long-sleeve henley, which comes in myriad colors, is made of a brushed rib cotton, resulting in a style that’s a throwback to the late ’60s. Slip it under a leather jacket or wear it on its own—there’s no wrong way to don this quintessential piece.

Material: Cotton.
Fit: Regular.
Colors Available: 6.


Best Casual Henley

Elevated basics you’ll want to wear everyday? Nobody does them better than purveyors of New York cool Rag & Bone. This henley perfectly pulls off a casual vibe without being drab, thanks to an attention to the details that matter, including a classic not-too-skinny fit, slightly frayed collar, and colorways that look lived-in.

Material: Cotton-jersey.
Fit: Slim.
Colors Available: 1.


Best Rugged Henley

Everyone is talking about Banana Republic’s new era, and this henley lives up to the hype. It’s made of a hefty jersey-cotton, brushed for extra softness. It’s rugged yet rakish, comfortable yet pulled-together. It will get plenty of mileage in your wardrobe.

Material: Cotton.
Fit: Slim.
Colors Available: 1.


Best Relaxed Henley

We’ve already extolled the virtues of having a henley in your rotation and offered a slew of options, each with distinct qualities for a variety of scenarios. But if you want a style that’s primed for lounging, a shirt that you get some Zzz’s in, look no further than Rhone’s loose and buttery Cloud 9  henley.

Material: Cotton, polyester, and spandex.
Fit: Regular.
Colors Available: 3.


Best Odor-Resistant Henley

Do you always find yourself out and about? Are you prone to sweating? Are you worried about building up a funk? Here to mitigate all that is Proof’s 72-Hour henley. As its name suggests, this shirt is constructed to regulate body temperatures, wick away moisture, and, most importantly, combat odors for up to, well, 72 hours—even after constant wear.

Material: Merino wool and nylon.
Fit: Slim.
Colors Available: 10.


Best Garment-Dyed Henley

Garment-dyed fabric, when made correctly, imbues a given piece with an unmissable riches. The process involves taking, say, an already constructed shirt and dipping it a color, as opposed using pre-dyed fabric. This gives it greater dimension. It gives it a worn-in look, an heirloom quality. And if you need an example, look no further this insulating beauty from Billy Reid. 

Material: Cotton and alpaca.
Fit: Regular.
Colors Available: 1.


Best Raglan-Sleeve Henley

Comfort lovers, take note of this henley from classic American brand L.L.Bean with raglan sleeves, which doesn’t have those pesky shoulder seams, so there’s no bunching or chafing. It’s made from American-grown Supima cotton, with just the tiniest hint of spandex, meaning it has a hint of stretch and an excellent, all-day fit.

Material: Supima cotton and spandex.
Fit: Regular.
Colors Available: 7.


Best Oversized Henley

A two- or three-button henley are the standard options available. But Massimo Alba takes the style a step further by offering five, giving wearers the ability to really unwind and feel that much more relaxed. Not to be outdone, of course, is the very roomy silhouette, which is ideal for reclining by the beach, by a roaring fire, or anywhere that’ll promote R&R. 

Material: Cotton.
Fit: Loose.
Colors Available: 3.


Best Two-Button Henley

The Normal Brand has earned fans across the country for its straightforward, quality basics, and it all began with this one shirt: the Puremeso henley. The brand’s custom cotton, polyester, and spandex blend is ridiculously soft and even undergoes a proprietary extra washing process to make it even softer. It’s as close as you may ever get to wearing a blanket outside of the house.

Material: Cotton, polyester, and spandex.
Fit: Regular.
Colors Available: 6.


Best Insulating Henley

In the colder months, each layer can make a difference. Contemporary brand Mack Weldon prides itself on “radically efficient wardrobing”—particularly this reliable Warmknit waffle-knit henley. It’s woven with Thermolite technology for tons of added warmth (think your favorite fleece or pair of insulated gloves) but with the weight of just a straightforward, cozy henley.

Material: Modal, Thermolite polyester, wool, and spandex
Fit: Regular.
Colors Available: 5.


Best Henley Pack

Every portfolio is all about diversity. Yes, the Tom Ford investment pieces and the fine Italian linens belong in your wardrobe—but so do the lower-cost options that you can feel guilt-free about buying in bulk, wearing to shreds, and getting dirty when the occasion calls for it. The henley, after all, was designed as something to sweat in. Look to Abercrombie & Fitch for an unfussy, uncomplicated pack that fits well, comes in a wide range of colors and more than gets the job done.

Material: Cotton and polyester. 
Fit: Regular.
Colors Available: 5.


Best Tailored Henley

You invest in your suits, so why not invest in a henley from Savile Row legend Anderson & Sheppard? It’s lightweight, with a long sleeve and a relaxed fit that screams “luxe fashion.”

Material: Cotton. 
Fit: Relaxed.
Colors Available: 3.


Best Crochet Henley 

This henley from Vince is made of cotton and polyester, two of lightest fabrics, which makes the use of the word “thermal” feel like a mistake. But it’s not. “Thermal” refers to the type of stitching used to construct the garment, a form of crocheting that creates a double and adds a bit of heft. 

Material: Cotton, polyester, and spandex. 
Fit: Regular.
Colors Available: 1.





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