Why the Henley Is Fall’s Most Unexpected Trend. Here’s Why You Should Care

THEY’VE BEEN CROPPING up everywhere. All over my social media feed, featured across men’s runway collections at Fashion Week, seen on Hollywood heartthrobs like Michael B. Jordan, and so forth. If you haven’t figured it out by now, I’m talking about the henley. This once-overlooked wardrobe staple has found new popularity, showing no signs of slowing down as it becomes one of fall’s most surprising menswear trends. And quite frankly, I’m here for it.The henley hasn’t traditionally been the sexiest shirt in a guy’s wardrobe. For years, it’s been the tee you’d throw on for a lazy Sunday or wear underneath a flannel. But somewhere along the way, the fashion crowd decided it deserved another shot. Its roots go all the way back to 19th-century England, where it started as an undergarment before becoming a go-to for rowers in Henley-on-Thames, hence the name. Who would’ve thought a shirt with such humble beginnings would eventually become a fashion obsession on my Instagram timeline?Here’s what I love about the henley: It does more heavy lifting than your average T-shirt without trying to be anything fancy. You get the simplicity of a crewneck, the button placket of a polo, and just enough texture to make an otherwise basic outfit feel put-together. And while the classic cotton version is still very much in rotation, ribbed, waffle-knit, and thermal styles are giving guys even more ways to wear it. If you need further proof that the henley is having a moment, just take a peek at the runways. For Fall/Winter 2026, Paul Smith sent a model down the runway in a white henley tucked into wide-leg black trousers, while Isabel Marant took a more layered approach, pairing a light blue henley with a navy corduroy jacket.I’m a firm believer that proportions can make or break an outfit, and the henley is no exception. My favorite way to wear one is with baggy jeans or relaxed trousers. The contrast between a fitted top and roomier bottoms creates a flattering silhouette. And if you’ve spent the past few months putting in work at the gym, a henley is one of the easiest ways to show off those gains without looking like you’re showing off. The closer fit naturally accentuates your chest, shoulders, and biceps, especially when you leave the top button or two undone. Just remember, there’s a fine line between fitted and too tight.Raymond Hall//Getty ImagesWhether you’re dressing one up with trousers and loafers or keeping things casual with loose jeans and boots, the henley proves that sometimes the most unexpected trends are the pieces we’ve had in our closets all along. And it’s about time this one received its flowers.More Men’s Fall EssentialsBest Polo Sweaters | Best Sweaters for Men | Best Chinos for Men | Best Hoodies | Best Men's Pajamas | Best Boots for Men | Best Corduroy Pants for Men | Best Crewneck Sweaters | Best Joggers | Best Sweatpants | Best Underwear | Best Travel Pants | Best T-Shirts | Best Cardigans for Men | Best Zip-Up Hoodies | Best Leather Jackets | Best Bomber Jackets for MenAs the Style and Reviews Editor for Men's Health, Joseph covers all-things fashion and grooming. Previously, Cheatham was a commerce editor for Spy, and he has written for Travel + Leisure.