There’s a feeling of tradition when you find yourself wearing a piece of clothing that Walt Whitman or Mark Twain might have worn. Of course, if either was seen in a henley, it was likely as underwear. The henley has been around since at least the mid-19th century when it was named for Henley-on-Thames, the town west of London that hosted the Henley Royal Regatta, where the collarless-styled shirt became popular with rowers who brazenly wore them right out in the open — no overshirt or boat jacket required.
In the early 20th century, the henley caught on in American baseball, too, with uniforms sporting the comfortable, unrestricting open-necked style, and it slowly asserted itself decade-by-decade, gaining a deeper foothold in our collective wardrobe. Today, the henley is the ubiquitous weekend uniform for Hollywood’s best dressed men, and sees countless interpretations in everything from sweaters to hoodies. But the classic, collarless button-up henley remains a versatile layer, worn under, over, or of course, all alone: laid back, comfortable, and timeless.
Grayers Double Cloth Henley
Grayers Double Cloth Henley is perfect for layering up in the fall. “All of our henleys have something special going on,” says Peter Georgiou, founder of the brand. “Our double cloth henley is inspired by a 1950s fabric we found in our archives. We spun yarns to create a heather slub texture with a double cloth oatmeal interior.” With a contrasting chambray placket and its two thin layers, it’s soft under a shirt or jacket, but a nice weight for covering as a top or middle layer. “It’s actually the perfect cross between a henley and a light-weight sweater,” Georgiou says. “We got the balance right.” [$75; Grayers.com]
Billy Reid Pensacola Henley
“With classic pieces like the Henley, which have been more signature pieces for us, we try to focus on maintaining the fit we’ve established, and use new fabric developments like yarn heathers, yarn dyes, stripes and textures — to keep it fresh,” says the eponymous designer, Billy Reid. With various versions, from his heirloom collection henleys to the different iterations of his Pensacola henley, he does just that. The Pensacola Natural has a yarn-dyed, reverse slub texture in its eye-catching stripe, with contrasting cotton sheeting in the collar and four button placket. [$69; billyreid.com]
Carbon2Cobalt Kinetic Henley
Carbon2Cobalt out of Santa Barbara is fond of the henley, featuring over a dozen unique variations. From clean, simple staples to character-rich heavier weights, they let the henley loose for a parade of expression. As founder Matt Cooper relates, “The Kinetic Henley was based on my desire to create a more rugged shirt. I’ve always liked the look of a henley neckline, but thought most options in the market were better as an under layer, not built to stand on its own.” The Kinetic is sturdy and perfect as a top layer, with rough edges, triple stitch reinforcement tape, and two layers of fabric. “It’s a rugged and manly exterior,” he adds, “with a soft, comfortable knit that embodies how I think most guys want to dress.” [$89; carbon2cobalt.com]
Homespun Knitwear Coalminer Contast Henley
J.Crew offers a handful of henleys from Vancouver’s Homespun Knitwear, which have gone back to its roots — inspired by the hard-working undershirts of the early 20th century, worn by “coal miners, iron workers and railroad men who relied on clothing that worked as hard as they did.” Unrefined cotton slub gives these henleys a sturdy feel and makes them ideal for their original purpose under a shirt, sweater, or jacket — but works on its own once you start peeling off those layers. Their Oldtimer Henley has cuffs on the sleeves for a vintage look, and the Coalminer Henley is an ode to the classic workshirt. [$95; jcrew.com]
Outlier Merino Ribbed Henley
Keeping their designs clean and minimal, Outlier from Brooklyn presents its straightforward henley in a superfine ribbed knit merino. “Some pieces just need to happen. We knew we’d be doing a henley the minute we first started working with merino.” While Outlier’s Zque certified New Zealand merino is great as a base layer, keeping you warm without leaving you clammy and uncomfortable if the weather shifts, Outlier agrees that it’s also “nature’s finest performance fabric.” Their henley is ideal anywhere in any climate, under a jacket or with a light sweater thrown on top. [$148; outlier.cc]
For access to exclusive gear videos, celebrity interviews, and more, subscribe on YouTube!