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 25 exceedingly comfortable—and surprisingly chic!—oversized men’s T-shirts to cop right now.
The Best Affordable Oversized Tee
Uniqlo U’s GQ-favorite T-shirts might get a lot of shine around these parts, but the brand’s main line is still putting out the kind of affordable, evergreen styles it’s famous for. This gently oversized pocket tee doesn’t come with the Lemaire stamp of approval, 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 scoop another handful in zesty shades of pastel when spring rolls back around. At just 20 bucks a pop, it’s affordable enough to stock up on—and way cheaper than the tees in your closet it’s about to supplant. What more can you really ask for?
The Best Extremely-Right-Now Oversized Tee
Demna—the mononymous 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 graphic 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. Balenciaga’s cotton-jersey T-shirt isn’t just oversized—it literally reminds you of its gargantuan proportions with a splashy “XXXL” chest embroidery that’s all kinds of cool…and laugh-out-loud funny. If you’re going to drop $600 on a walking billboard, it might as well telegraph your allegiance to the biggest designer on the planet—and make a few people chuckle along the way.
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 Soft-As-Hell Oversized Tee
As a guy who made a name for himself reworking grail-worthy vintage tees in the 2010s, Jerry Lorenzo is keenly attuned to the nuances that make a T-shirt worth the price of a very long, very boozy night out. Today, the Fear of God designer cuts some of the sickest power tailoring in the biz, but his tees remain the easiest way to buy into his expansive, Kenny G-inspired (!) vision. This one’s technically a pajama shirt, but, like the type of shorts it’s designed to be worn with, it’ll look just as rad during the day. The cotton jersey fabric has a touch of stretch for added comfort, the cut is oversized but not aggressively so, and the tonal leather logo on the back is a flex every T-shirt obsessive you know will appreciate. You could wear it to bed, of course, but if the only people who see you in it are your drowsy-eyed roommates, you’d be depriving that beefy overshirt you just bought of a new best friend. (And if you don’t want to shell out top dollar for the main collection, FOG’s Essentials sub-label sells an absolutely killer 3-pack too.)
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 Artfully 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 and sturdy derby shoes or thrashed jeans and scuffed Jordans and you’re good to go.
The Best Ridiculously Luxe Oversized Tee
It’s a rarified few that can afford to drop a cool $1,000 (we’re rounding down here, but what’s a couple hundred bucks between friends?) on the simplest item of clothing in their closet. Thankfully, Loro Piana has never been all that concerned about catering to the masses. Instead, the pedigreed Italian fabric house focuses on the type of quietly decadent clothing you’re apt to see on Succession, all of it cut from the highest-quality fabrics in the world. Naturally, the brand’s oversized, dropped-shoulder tee comes done up in the absurdly luxe cashmere the company specializes in, with a healthy amount of silk in the mix for added drape. Which means it’s relaxed in the most literal sense of the word; if you’re wearing it, you probably haven’t had a real worry since you made your first million in the ‘90s dot com bust. Dropping a month’s rent on a tee is a fairly ludicrous proposition, sure, but it’s weirdly comforting to know that the option exists—after all, what else is there to aspire to when you’re rapping along to “L to the OG” from the couch?
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