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 relaxed fit pocket 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

John Elliott Folsom oversized T-shirt

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

Balenciaga medium-fit 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

Carhartt K87 workwear pocket T-shirt

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.

16 More Oversized Tees We Love

Dries Van Noten medium weight oversized boxy T-shirt

Dries Van Noten, the feted Belgian designer famous for his bright prints and patterns, doesn’t work with black all that often. So when he does, it’s worth paying attention. Bonus points if you commit to the bit and pair this with flowy pants and sandals.

Our Legacy new boxy T-Shirt

“Boxy” doesn’t have to mean comically gargantuan. Case in point: this exactingly-cut tee from the Swedish design gurus at Our Legacy.

Wardrobe NYC oversized T-shirt

Wardrobe NYC specializes in the kind of garms that make up the building blocks of your everday rotation. Looking for the perfect heather gray oversized T-shirt to rock with swishy shorts or slim—but not skinny!—jeans? Look no further.

Jil Sander oversized T-shirt

When it comes to plain white tees, too many brands overlook the all-important width of the crewneck. Not Luke and Lucie Meier, the husband-and-wife duo charged with revitalizing Jil Sander. Theirs comes with a classic skater tee fit and a snug neck that’ll hold up over time, keeping you locked in on the prize: getting fits off.

Ninety Percent boxy organic cotton T-shirt

If the cool blue hue wasn’t enough to convince you, Ninety Percent promises to donate a whopping, well, 90% of the proceeds here to the charity of your choice. Who doesn’t love a come-up with a happy ending?

Abercrombie essential oversized pocket tee

Muted earth tones? Retro-leaning stripes? Abercrombie’s pocket tee proves the brand is officially putting the kibosh on the bicep-strangling styles of old.

J.Crew relaxed hertiage oversized T-shirt

J.Crew’s ’90s-indebted tee comes in range of bright, saturated colors, ready-made for your next trip to Malibu. No guarantee they’ll help you hobnob with the glitterati at Nobu, but at $50 a pop you’ll have plenty of extra dough to splurge on black-cod miso.

Nike premium boxy oversized T-shirt

Big, boxy tees deserve a spot in your gym lineup too. Nike’s version is a far cry from the NFL Combine—it’s as sleek as you’d expect from the first name in performance sportwear, and might actually make you excited to pump some iron.

Willy Chavarria oversized T-shirt

The ideal version of a thrift store come-up, down to the biker-inspired graphic and ’90s fit. Who said badasses can’t be cozy?

Cos regular fit boxy T-shirt

If you’re looking to completely ditch your slim fit tees in favor of their new oversized counterparts, you’ll need an option you can buy in bulk. COS’ $30 version keeps the trim sleeves, but swaps the longer length for a cropped body you’ll never have to worry about tucking.

Dickies short sleeve pocket tee

Partial to Dickies over Carhartt? They make some killer tees, too.

Lady White Co Athens T-shirt

That really cool guy you know who always looks impeccable in a plain tee? He’s wearing this.

Kirkland Signature crew neck t-shirts (6-pack)

Size up for maximum relaxed-ness.

Mooji Mooji oversize crop t-shirt

Fresh-off-the-rack vintage vibes without any of the actual mileage.

Everybody.World recycled cotton boxier trash tee

Boxier, shorter, and greener than the majority of tees you’ll come across, the cropped cut works well with high-rise pants (or showing off a little midriff).

FGS Originals classic pocket t-shirt

Heavier than the self-touted beefy tees out there, this one is for people who like ’em dense and baggy.



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