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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 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 20 exceedingly comfortable—and surprisingly chic!—oversized men's T-shirts to cop right now.
The Best Oversized Tees Shopping Guide
- The Best Affordable Oversized Tee: Uniqlo oversized pocket crewneck T-shirt, $20
- The Best OG Oversized Tee: Carhartt K87 workwear pocket T-shirt, $20
- The Best Oversized Tee with a Little Somethin'-Somethin': Buck Mason slub 90s Boxy tee, $45
- The Best Vintage-Looking Oversized Tee: John Elliott reversed cropped tee, $138
- The Best Galaxy-Brain Oversized Tee: Jan-Jan Van Essche O-Project T-shirt, $245
- The Best Outrageously Expensive Oversized Tee: Fear of God Eternal oversized wool-blend crepe T-shirt, $1100
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 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 Oversized Tee with a Little Somethin'-Somethin'
Plucked off the back of a ‘90s silver screen lead, the Buck Mason tee is great for pairing with some billowy trousers and some dressy shoes like an off-duty desk jockey. The 145 GSM cotton jersey fabric is knit in the USA, but what sets apart this Buck from the rest is it's slightly slubby texture. It's the kind of detail that's enough to tell people that something different is going on here, but doesn't knock you over the head like other slubby tees might. And as we head for warmer weather, it's an easy way to toss in some visual interest without resorting to extra layers.
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 Galaxy-Brain Oversized Tee
Jan-Jan Van Essche is a wizard in the fashion world. Though he only just made his debut on the runway, he's had his label since 2010 and has built a dedicated fan base that knows him for his high-level patterning skills, warm and somber color palette, and gorgeous shapes. And when he takes to something as basic as a tee, you can expect it to be well, not so basic. This tee which is part of his newly launched O-Project label, features a breezy hemp blend fabric that's perfect for the equally cavernous silhouette. But what's more fascinating is that the tee is devoid of any shoulder seams which gives it a totally natural shape. So, yeah, the next time someone asks you about your T-shirt, you can just link them to this little blurb instead of giving them a sermon.
The Best Outrageously Expensive 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. And by “easy” we mean the easiest to wear. This bonkers tee is astronomic at $1100 (that's 55 Uniqlo U tees). If you're seriously considering this tee to fill out your basics drawer, you're probably not worrying about much, let alone finding the easiest entry point into Mr. Lorenzo's world. The Eternal tee is made of a gorgeous wool-blend crepe fabric that's been doubled to give the tee a mesmerizing drape that has a structured sway not unlike a Savile Row suit. And like a suit, this puppy is dry clean only (or save yourself some trouble and cop some undershirts).
Plus 13 More Oversized Tees We Love
Everybody.World Boxier tubular Trash tee
Everlane premium-weight relaxed crew
The Row Dlomu wool-jersey T-shirt
Front General Store wide boxy tee
