Fashion Men's Fashion

The 17 Best Oversized T-Shirts for Men in 2020

Hits: 19

Yes, oversized T-shirts for men 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 2020 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 nine best versions from across the fashion spectrum for you to cop right now.

The Best Vivid Oversized T-Shirt

Entireworld organic cotton boxy T-shirt

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.



Buy Now

The Best Heavy-Duty Oversized T-Shirt

Everlane heavyweight relaxed crew

If you like a little extra heft to your 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.



Buy Now

The Best Next-Level Oversized T-Shirt

John Elliott University tee

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 stuff is 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.

John Elliott


Buy Now

The Best OG Oversized T-Shirt

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.

Buy Now

The Best Sculptural Oversized T-Shirt

COS relaxed cotton jersey sweatshirt

The most voluminous silhouette on this list—but also the most structured, thanks to a burly sweatshirt-like fabric. It’s minimalist, sure, but also distinctly luxe and artful and elevated. In other words, you can show up to all manner of fancy places in this thing, and no one’ll ever wonder why you’re “just” wearing a tee.

Buy Now

The Best Affordable Oversized T-Shirt

Uniqlo U oversized crew neck T-shirt

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.

Buy Now

11 More Tees We Love

Dickies short sleeve pocket tee

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

Buy Now

Acne Studios oversized cotton-jersey T-shirt

The Swedes really know their way around a big, clean-lined basic.

Mr Porter


Buy Now

Noah recycled cotton tee

Noah’s heavyweight tees are crafted from 100% recycled cotton.

Buy Now

Missoni multicolor striped logo T-shirt (was $270, 35% off)

Bigger tees mean more surface area for Missoni’s eye-popping stripes.




Buy Now

Armor-Lux 71990 classic tee

About as universally flattering as any shade of yellow can get.

End Clothing


Buy Now

Club Monaco short sleeve boucle crew

Thanks to its nubby texture and elastic hems, this tee fits just like that sweater polo you’ve been wearing non-stop since the quarantine started.

Club Monaco


Buy Now

Story Mfg. Grateful tie-dyed organic cotton-jersey T-shirt

Advanced-level tie-dye.

Mr Porter


Buy Now

Rick Owens black heavy jersey T-shirt (was $650, 64% off)

You really thought we were going to talk giant tees without a single mention of Rick Owens?




Buy Now

Banana Republic supima cotton boxy T-shirt

Even Banana Republic’s getting in on the oversized action these days.

Banana Republic


Buy Now

120% slim-fit striped linen T-shirt

Drapey and breezy and perfect for summer.

Mr Porter


Buy Now

Visvim jumbo T-shirt

Is any T-shirt really worth $580? Only one way to find out.



Buy Now

Continue Reading

You may also like...

Leave a Reply

Your email address will not be published.

two × 3 =