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Your T-Shirt Doesn't Need to Be Tight. Try an Oversized One

Go big or go home.

man in richer poorer relaxed tee
Richer Poorer

We're long removed from the era of tall tees and ultra-wide JNCO jeans, but oversized T-shirts haven't completely disappeared. Bigger fits are in, a trend triggered by the comfort we grew accustomed to during the pandemic. Relaxed-fit dress pants, chunky sneakers, big bucket hats and, of course, boxy tees are everywhere.

How to Wear an Oversized T-shirt

The secret to pulling off an oversized T-shirt is to remain relaxed-fitting in the rest of your outfit. Oversized tee? Try wider-fitting chinos and substantial sneakers. If you contrast an oversized T-shirt with skinny jeans, you're not proving you aren't the Michelin Man underneath; you're toying with your silhouette too much. It'll just look odd. That being said, your wardrobe shouldn't be a metaphorical Matryoshka doll, with each subsequent piece being bigger than the last. Try to keep a balance throughout. So, one last time, if your shirt is oversized, try to pair it with regular-fit jeans and Chelsea boots or a basic sneaker.

What to Avoid

You want it to be oversized, not big. It's important to always order true to size. Because the T-shirt is designed to be, well, big, going a size up will take it too far. You'll no longer look like you dressed this way on purpose, but that you simply don't know your size (or how clothes should fit). Save your droopy, dress-length T-shirts for bed time.

Here's a good way to be sure your shirt isn't too big: the sleeves shouldn't hang past your elbows, and the tail shouldn't go beyond the bottom of your butt.

8 Oversized T-shirts for Men

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Best Overall Oversized T-shirt
Richer Poorer Relaxed Tee

Richer Poorer's Relaxed Tee is just right: not too long or too boxy, but roomy. It has oversized neck and sleeve stitching, dropped shoulders and a pigment-dyed, vintage-tinged look about it.

Best Upgrade Oversized T-shirt
Darryl Brown DB T-shirt

Darryl Brown sources most of his inspiration for his eponymous label from workwear. This made in USA tee speaks to this influence, but thoughtfully mixes in some streetwear, too.

Best Budget Oversized T-shirt
Standard Cloth Shortstop Tee

Where the sleeves hang depends on your arm length. (Some folks can be 6'0" but have a 6'4" wingspan.) Standard Cloth's Shortstop Tee has sleeves that should hit right at your elbow (or slightly above it), which is exactly how an oversized tee should fit.

Everlane The Premium Weight Relaxed Crew

Everlane's entry isn't quite oversized, but maybe a little big. It won't fit like your skinny-slim compression shirts, or even like an undershirt, but rather differently because of its weight and how it's cut. The shirt is heavier — 6.2 oz — and has dropped shoulders. The weight helps it hang better.

Uniqlo U AIRism Cotton Oversized Crew Neck T-Shirt

Designed by Christophe Lemaire, founder of his own eponymous luxury label and artistic director for Uniqlo U, the AIRism Oversized Crew Neck T-shirt calms concerns that the additional fabric needed to make a shirt oversized will make you overheat. AIRism Cotton is super breathable and soft.

Kotn Relaxed Crew

With a slightly scooped (aka bigger) neck and dropped shoulders, Kotn's Relaxed Crew is clearly oversized. It comes in three colors and sizes XXS through XXXL.

Abercrombie & Fitch Essential Oversized Pocket Tee

A&F might've once specialized in form-fitting tees and tight jeans, but the brand has grown — literally. It sells several oversized items — including this tee. It has a pocket on the front and a thick, raised collar.

PS Basics Loch Solid Boxy T-Shirt

Look at the hems where the sleeves were attached. They're pretty far down, right? Those are called drop shoulders, a term for shifting the sleeve further down the arm. Combine this design choice with the tee's natural roominess and you've got an oversized tee to a tee.

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