Everyone has a defining henley shirt moment. Maybe yours involved watching a grease-stained, taciturn Ryan Gosling cut down everyone that isn’t Carey Mulligan in Drive. Maybe it involved watching Kanye West rock any number of versions while doing a string of internet-breaking press runs in the early 2010s. (Were we ever so young?) Maybe it involved watching your old man tinker with the leaky faucet in the bathroom before throwing in the towel—literally—and finally calling a plumber. Or, hell, maybe it involved reading this here story right now!
Either way, we’ve all got one: the moment that first made you think damn, I should really buy a henley. This is because the henley is far more than a standard tee with a few buttons added in for visual interest (or, for that matter, a polo with the collar lopped off). No, sir. To dismiss it as such would be a grave disservice to notable henley-wearers around the world—Gosling, West, and your father figure very much included. The henley earned its reputation as a go-to layer for men as varied as the three above through its sheer versatility, sure, but also because it boasts a flattering design even the most ardent T-shirt devotee can get behind. Which makes it an ideal foundational piece to build any cold weather outfit around, whether you’re rocking it solo with the heat cranked up indoors or as a base layer beneath all your puffiest winter finery.
So to any and all henley novices out there: welcome to your moment. Relish it. You really only get one. To help make sure you don’t screw it up, here are 20 of the best henley shirts to buy right now. And for what it’s worth, you might want to make like Pops and call in the professionals to take a look at that sink. A good henley can do a lot, but even the best can’t turn you into the handyman you always wished you were.
The Waffle Henley Shirt
Everlane’s henley is made out of a sturdy 100 percent cotton that offers peak coziness without compromising a bit on durability.
Pima Curved Hem Henley
Buck Mason
Buck Mason made a name for itself selling perfectly cut tees with a flattering curved hem. Thankfully, the brand takes that same approach when it comes to cheffing its smash-hit henleys, signature curved hem and all.
Lightweight Waffle Henley Shirt
An elevated take on an otherwise casual style that suddenly makes the henley look a whole lot more like a sweater than a tee.
5 Year Basic Long Sleeve Henley
Looking for a style you could conceivably work out in, but definitely won’t? Look no further.
Long-Sleeve Pocket Henley T-Shirt
The only henley noted connoisseur of good taste Action Bronson swears by.
Long Sleeve Waffle Henley
Wrangler Authentics
A thermal knit in a dusty shade of olive green that hearkens back to the style’s historic popularity with U.S. military members across the globe.
Garment-Dyed Slub Cotton Henley Shirt
Garment-dyed goodness of the brand that very seldom does things wrong.
Logo-Appliquéd Waffle-Knit Cotton-Jersey Henley T-Shirt
Fear of God Essentials
It doesn’t get any more essential than this henley, folks.
Madewell Doubledown Cotton Henley Shirt
You know what’s better than a henley shirt? A striped henley shirt.
Warmknit Waffle Henley
Mack Weldon
This henley is red-hot—and in more ways than one, too.
Triblend Stripe Henley Shirt
Marine Layer
If there is one name to know in the henley game, it is, without a doubt, Marine Layer.
Bamboo Flex Henley Shirt
Cut from a soft, but substantial (body goals!) bamboo blend fabric, this henley isn’t just a warm layer on nippy winter nights; it’ll keep you looking cool throughout the rest of the year, too.
Katahdin Iron Works Bonded Waffle Fleece Henley Shirt
A top for a long day outdoors (or, like, curled up in front of the TV). Let’s just say the inner lining of plush berber fleece is a game-changer.
Muse Long Sleeve Henley T-Shirt
This AllSaints henley is so pure that it should be canonized.
Made in L.A. Short Sleeve Jersey Henley
Todd Snyder
The easiest way to trick your family and friends into thinking you’ve been working out at home throughout the past year? Rock a henley cut to flatter your biceps, no matter how long it’s actually been since you did a single push-up.
Sun-Faded Long-Sleeve Slub Scallop Henley
Scallops: always a treat, no matter how they’re served.
Louis Henley Shirt
Billy Ried
Subtlety, more often than not, makes the most everlasting impact, and this here henley is proof of that credo.
Waffle-Knit Cotton Henley
The Kanye choice—or close to it.
Recycled Cashmere Henley
From the tapered sleeve to the slimming fit to the (most importantly) recycled cashmere, this henley is a must-cop this winter.
Beam Henley Long-Sleeve Shirt
A-COLD-WALL*
If loving ribbed detailing is wrong, I don’t wanna be right.
Barry Samaha Barry Samaha is the style commerce editor at Esquire, where he covers all things fashion and grooming.
Avidan Grossman Avidan Grossman is the Style eCommerce Editor at Esquire, covering men’s fashion, shoes, grooming, and accessories.
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