THE JOURNAL
Austin Butler at the screening of Caught Stealing in Puerto Rico, 8 August 2025. Photograph courtesy of Sony Pictures
Almost all of the menswear you love started out as a functional uniform for some occupation outside the fashion industry. Trench coats, blouson jackets, cargo pants and desert boots, for example, can all be traced back to the military. And those Carhartt double-knees you live in would never have been on your radar were they not endorsed by the world’s blue-collar workmen decades ago.
The sports industry has had a big hand in shaping modern menswear, too. And few athletic garments have had such staying power as the classic Henley. Named after Henley-on-Thames, the quaint British town and spiritual home of competitive rowing, the simple shirt once represented the cutting edge of sportswear. Cut from lightweight cotton and featuring a collarless neck opening and short placket with just a few buttons, the Henley was first designed as a base layer, but 19th-century rowers adopted it for its breathability and ease of movement. The Henley soon became standard dress across the sport.
But it didn’t take long for the Henley to expand beyond the riverbanks of Oxfordshire. By the early 20th century, it had evolved into a do-anything, every-guy base layer. In the UK, you might see one poking out from beneath a dress shirt, whereas across the Atlantic, the Henley had been reappropriated as a piece of hardy workwear, often cut from thermal fabrics. Cowboys wore Henleys, the Peaky Blinders wore Henleys. You get the picture.
A century later and the Henley’s vibe has softened, though not completely. No longer just a base layer, the Henley now sits alongside crew necks and polos in the pantheon of everyday T-shirts, but its macho, outdoorsy edge sustains. Just ask the hard men of Hollywood – Idris Elba, Michael B Jordan, Alan Ritchson, etc – who seem to have claimed it as the movie industry’s official muscle tee.
Daniel Craig in No Time To Die (2021). Photograph by LANDMARK MEDIA/Alamy Stock Photo
“Actors in particular love Henleys because they frame the torso in a flattering way,” says London-based celebrity stylist Tom O’Dell. “There’s a reason costume designers reach for them so much. They’re masculine without being stiff, casual without being sloppy and adaptable across eras and settings. My clients usually find them surprisingly confidence-boosting and familiar once they try one on.”
The Henley can be sleek, too. It has a hard-wearing heritage, O’Dell adds, “but in the right fabric and fit, it can be refined. Think fine-gauge cotton or merino under tailoring and it feels intentional.”
O’Dell says that the fabric of a Henley is key to understanding its vibe. “Heavier cotton jerseys or waffle knits give a vintage, workwear edge,” he says, while “lighter merino wool or pima cotton make it sleeker.”
Keep an eye on the hardware, too. Look for corozo or even horn buttons as a tell for quality – and avoid plastic buttons.
Simple cotton Henleys still pervade at the likes of rag & bone, RRL and James Perse, but that refinement that O’Dell describes has also been recognised by high luxury brands, including Brunello Cucinelli, TOM FORD and Loro Piana. In its current collection, ZEGNA has a Henley in its super lightweight Oasi linen, replete with mother-of-pearl buttons, while Loro Piana has reimagined the Henley as a sweater. Cut from chunky cotton, it’s designed to sit off the shoulder for maximum cozy comfort.
Fit-wise, a slim cut is preferable, especially if you’re planning to layer over the top, or if you want it to accentuate your physique. The classic ribbed cotton design, such as that by Brunello Cucinelli, is best for big muscles, O’Dell says. Just make sure it’s not so tight that the placket bulges out or splays open.
“A Henley works best when it’s treated as a foundation piece,” O’Dell says. He notes how the buttons peeking out from underneath a collar can add a little interest to an otherwise low-key look.
“I’d wear it with vintage denim and desert boots, or a nice pair of classic Converse for something timeless,” O’Dell says. “You can even wear it under an unstructured blazer. Or an overshirt, to smarten it up.”
And there’s always the option to take the Henley back to its roots and pair it with chino shorts, a rowing blazer and boat shoes. Although perhaps that sartorial ship has sailed.
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