Yes, oversized men’s T-shirts are back. But don’t worry: We’re not about to tell you to start dressing like Soulja Boy circa 2007. Thankfully, the oversized tees we’re talking about are not of the quintuple-XL, Elizabethan-gown-length variety that all ringtone rappers were required by law to wear in their music videos. Instead, like the Dickies and Vans everyone’s wearing again, the raddest tees in 2022 take direct inspiration from ’90s skateboarders: boxy and baggy and strangely flattering, cut from crisp, weighty cotton that’s anything but sloppy.
Since you can suddenly find these bigger, badder T-shirts everywhere from the mall to the runway, we took the liberty of searching out the very best from across the fashion spectrum. Here are 21 exceedingly comfortable—and surprisingly chic!—oversized men’s T-shirts to cop right now.
The Best Affordable Oversized Tee
Gap might be making headlines for its more recent collaborations, but the brand’s main line is still putting out the kind of affordable, evergreen styles it’s famous for. This relaxed-fit pocket tee doesn’t come with a double scoop of clout, but it’s also available to buy whenever you want, no wait necessary. We’ve spent years trying to crack the science behind why a simple pocket can make a T-shirt go from feeling like underwear to a thoughtful top layer in its own right during the warmer months. The data is still rolling in, but the point remains: you can wear this with just about anything in your closet and never feel underdressed. Load up on a handful of ’em in classic white now, and then pivot to Nantucket-ready pink when summer really hits its stride.
The Best Vintage-Looking Oversized Tee
Pre-distressed clothing makes for a controversial topic of conversation in the fashion world, but it’s a debate we’re ready and willing to have. The thing is, you could absolutely find a cool ripped T-shirt scouring eBay, but you’ll likely never come across one as perfect as John Elliott’s. And finding it again in the wild? Nearly impossible. The L.A.-based designer geeks out on old clothing, which is why the tasteful holes and rips you see here are added in places where, you know, they’d actually occur out in the real world. We wouldn’t recommend doubling-down on the distressing when it comes to pants, though—instead, opt for either clean, dark denim or some gussied-up mesh shorts.
The Best Subtle Flex Oversized Tee
When it comes to logos, best to err on the side of subtlety. The sans-serif typeface on Balenciaga’s tonal T-shirt is so discreet you’d almost miss it…which is kind of the point. Demna—the mononymous creative mastermind behind Balenciaga’s hot streak—is, above all else, a master of silhouette, tweaking and re-tweaking the familiar tropes of the modern fashion lexicon until they take on a startling new relevance. In his hands, the humble tee is elevated to the realm of high fashion via a couturier’s eye for proportion, a nifty trick few designers manage with his particular brand of winking humor. If you’re going to drop $600 on a tee, it might as well telegraph your allegiance to the biggest designer on the planet—no matter how long it takes for anyone to notice that logo.
The Best OG Oversized Tee
The workwear stalwarts at Carhartt were ahead of the game on this whole oversized tee movement: their weighty, boxy K87 model has been a go-to among power-tool-bearing professionals and in-the-know skateboarders alike for ages. Thankfully, the label hasn’t chosen to price gouge now that the silhouette is in vogue—so you can still pick one up for just $17 a pop.
The Best Cropped Oversized Tee
Brought to you by a pioneer of the new workwear movement, this hyper-relaxed tee isn’t just big. It’s also cropped to a perfect length so you don’t look like you’re wearing a shirt that used to belong to Shaq. Pair it with high-waisted chinos or thrashed jeans and some vintage Jordans and you’re good to go.