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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 2021 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 17 exceedingly comfortable—and surprisingly chic!—oversized men’s T-shirts to cop right now.
The fit (just slightly oversized, a good way to ease in to the trend) and fabric (comfy organic cotton) are both on point here, of course—it wouldn’t have cracked a Best Stuff list otherwise. The biggest selling point on this Entireworld slapper, though, is probably the palette: Beyond this minty fresh number, this exact shirt comes in a baker’s dozen of fetching hues and a whole bunch of breezy stripes. Stock up for summer.
If you like a little extra heft to your loose fit tees, this is the one you want. It’s cut from thick 6.2 ounce cotton, so you won’t have to worry about anything unwanted showing through on an unexpectedly breezy day or be concerned it won’t survive more than a couple of rounds in the washing machine.
It’d be easy to pigeonhole John Elliott as “that slouchy basics dude”—but if that was the L.A. designer’s whole schtick, we’d just tell you to buy some tees at PacSun and call it a day. What helps Elliott transcend those labels—the reason his hoodies and sweatpants and tees are beloved by everyone from LeBron to Whoopi to your pals right here at GQ—is his staggering attention to detail. The proportions are exacting: a little extra length, but not so much that it feels like a sleep shirt; a roomier neckline that doesn’t dip into unfortunate scoop-neck territory. Toss in the soft-as-hell recycled (!) cotton and that exquisitely lived-in washed black, and you’ve got yourself a slouchy tee truly worth splurging on.
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.
Another day, another Christophe Lemaire banger for Uniqlo U. Three things this shirt has that none of the others we’ve mentioned do: a handy phone-sized chest pocket; a tennis-shirt-inspired split hem; and a pricepoint lower than what you spent on lunch at Sweetgreen yesterday.
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.
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