17 best oversized men’s t-shirts in 2021: Carhartt, Everlane, John Elliott and more


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 around 2007. Luckily, the oversized t-shirts we’re talking about aren’t the quintuple-XL, dress-length variety. Elizabethan ringing all. rappers were required by law to wear in their music videos. Instead, like the Dickies and Vans everyone wears again, the most radiant tees in 2021 take direct inspiration from ’90s skateboarders: boxy and baggy and weirdly flattering, cut from crisp cotton and heavy which is anything but sloppy.

Since you can suddenly find those bigger, meaner tees everywhere from the mall to the runway, we’ve taken the liberty of searching for the best of the entire fashion spectrum. Here are 17 super comfy and surprisingly chic oversized t-shirts for men to wear right now.


The best vivid oversized t-shirt

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Entireworld organic cotton square T-shirt

The fit (just slightly oversized, a nice way to keep up with the trend) and the fabric (comfortable organic cotton) are both in the spotlight here, of course – it wouldn’t have made a list of Best Stuff otherwise. Probably the biggest selling point of this Entireworld slap, however, is the palette: Beyond that fresh minty number, this exact shirt comes in a dozen eye-catching hues and a whole bunch of breezy stripes. Refuel for the summer.

The best durable oversized t-shirt

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The laid-back Everlane heavyweight crew

If you like a little extra weight for your loose t-shirts, this is the one you want. It’s cut from 6.2 ounce heavy cotton, so you won’t have to worry about anything unwanted showing up on an unexpected windy day or worrying it won’t survive more than a few turns in the day. washing machine.

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The best next-level oversized t-shirt

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John Elliott University T-Shirt

It would be easy to categorize John Elliott as “that slouchy basic dude” – but if that was all the LA designer schtick, we’d just tell you buy some t-shirts from PacSun and call it a day. What helps Elliott transcend those labels – the reason his hoodies, sweatpants, and t-shirts are loved by everyone from LeBron to Whoopi to your friends here at GQ – is his incredible care for the detail. The proportions are demanding: a little more length, but not to the point of resembling a nightgown; a looser neckline that doesn’t dive into the unfortunate territory of the scoop neck. Add in the hell-soft recycled (!) Cotton and that delightfully lived-in washed black, and you’ve got a loose fitting tee that’s definitely worth splurging on.

The best OG oversized t-shirt

Carhartt K87 Workwear Pocket Tee

The mainstays of workwear at Carhartt were ahead of the game on this whole oversized tee movement: their heavy, boxy K87 model has been a staple among power tool wearers and savvy skateboarders for ages. Thankfully, the brand hasn’t chosen to jack up the prices now that the silhouette is in vogue, so you can still pick one up for just $ 17 a piece.

The best affordable oversized t-shirt

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Uniqlo U Oversized Round Neck T-Shirt

Another day, another bang from Christophe Lemaire for Uniqlo U. Three things this shirt has that none of the others we’ve mentioned have: a handy chest pocket the size of a phone; a split hem inspired by a tennis shirt; and a price lower than what you spent yesterday for lunch at Sweetgreen.

The best tall and short t-shirt

Brought to you by a pioneer of the new workwear movement, this hyper-relaxed tee isn’t just big. It’s also cut to the perfect length so you don’t look like you’re wearing a shirt that once belonged to Shaq. Pair it with high waisted chinos or ripped jeans and vintage Jordans and you’re good to go.

11 other t-shirts we love

Dickies Short Sleeve Pocket Tee

Partial to Dickies on Carhartt? They also make killer t-shirts.

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Noah Recycled Cotton T-Shirt

Noah’s heavyweight t-shirts are made from 100% recycled cotton.

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Lady White Co Athens T-shirt

That really cool guy you know who always looks impeccable in a plain t-shirt? He’s wearing this.

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Beams Plus Jacquard Stripe Pocket T-Shirt

Major Sand vibrations.

Knickerbocker Ribbed Pocket T-Shirt

In addition to a relaxed primo fit, a wide ribbed texture gives this tee a sleek drape that’s hard to find in a tee.

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Kirkland Signature Crew Neck T-Shirts (6-Pack)

Trim above for maximum relaxation.

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Acne Studios Relaxed Fit T-Shirt

A raised plain t-shirt for an ever so subtle flex.

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COS relaxed fit hemp t-shirt

If your main goal when putting on an oversized t-shirt is optimal temperature regulation in hot climates, this t-shirt is for you. The 100% hemp construction makes it very airy and breathable, like carrying a refrigerator, only a lot lighter.

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Mooji Mooji Oversized Cropped T-Shirt

Vintage vibes fresh out of the rack without any real mileage.

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Everybody.World Recycled Cotton Boxer Bin T-Shirt

Squareer, shorter and greener than the majority of t-shirts you’ll come across, the cropped fit works well with high waisted (or showing a small tummy) pants.

Gap Oversized Pocket T-Shirt

Beg, just begging, to wear with wide khakis and moccasins.
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Celine Homme + Tyson Reeder printed cotton jersey T-shirt

When is a T-shirt more than just a T-shirt? When it’s a work of art.

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FGS Originals Classic Pocket T-Shirt

Heavier than the beefy t-shirts they brag about, this one is for people who like them dense and loose.

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