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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.
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.
Here, we’ve pulled together 15 of the best henley shirts for men.
Best Waffle-Knit Henley
Onia Waffle-Knit Henley Shirt
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 but is still lightweight enough to wear in warmer climates.
Best Linen Henley
120% Slim-Fit Linen Henley Shirt
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 comes with a five-button placket that quietly and elegantly makes a statement.
Best Vintage-Inspired Henley
Sunspel Paul Weller College Henley Shirt
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. This particular version comes in a vintage style made from substantial cotton pique, inspired by a piece from British rock icon Paul Weller’s archive. Note the curved hem.
Best Luxury Henley
Tom Ford Silk Cotton Rib Henley
Nobody understands sexy, slinky better than Tom Ford. This long-sleeve henley is exactingly crafted from a truly luxurious blend of mulberry silk and organic cotton, 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.
Best Jersey Henley
Barena Venezia New Jersey Henley Shirt
Don’t confuse the name of Barena’s luxe “New Jersey” cotton jersey fabric with the Garden State. It’s 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—particularly with the shirt’s carefully constructed yet effortless curved hem.
Best Casual Henley
Rag & Bone Classic Flame Long Sleeve 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 and the brand’s signature metal buttons.
Best Colorblock Henley
J. Crew Waffle Baseball Henley
Don’t forget about color when building up your quiver of henley shirts. Some colors wax and wane in popularity, but a good color-blocked piece will stand the test of this time, such as this J. Crew option, a throwback to classic baseball jerseys. Slip it under a leather jacket or wear it on its own—there’s no wrong way to don this quintessential piece.
Best Raglan-Sleeve Henley
L.L.Bean Comfort Stretch Pima Henley Shirt
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.
Best Three-Button Henley
Massimo Alba Giamaica Jersey Henley Shirt
The choice of a two- or three-button henley (or more) comes down to two things: what looks better with your proportions and personal preference. If you’re more of a three-button guy, this luxe Massimo Alba option gets the promotions just right. It has a regular fit, mother-of-pearl buttons and is made in Italy from a smooth, durable cotton and poly blend.
Best Two-Button Henley
The Normal Brand Puremeso Two-Button Henley Shirt
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.
Buy Now on The Normal Brand: $65
Best Sustainable Henley
Hemen Biarritz Niko Slim-Fit Striped Organic Cotton-Jersey Henley Shirt
Turn to French cult classic brand Hemen Biarritz for sustainable henleys made from organic cotton. Not only does it have a flattering slim-fit, but it also offers that certain je ne sais quoi.
Best Striped Henley
Banana Republic Brushed Waffle-Knit Henley
Everyone is talking about Banana Republic’s new era, and this henley is a perfect example. It’s made of a waffle-knit material that’s been brushed for extra softness and comes in a smart stripe pattern that will stand the test of time. It’s comfortable yet pulled-together and will get plenty of mileage in your wardrobe.
Buy Now on Banana Republic: $75
Best Insulating Henley
Mack Weldon Warmknit Waffle Henley Shirt
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.
Best Henley Pack
Abercrombie & Fitch Five-Pack Icon Henley Shirt
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.
Buy Now on Abercrombie & Fitch: $75
Best Tailored Henley
Anderson & Sheppard Knitted Cotton Henley Shirt
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.”
