Here's How to Wear a Comfy, Giant T-Shirt and Still Look Stylish (Seriously)

I don't know about you, but some days all I want to do is put on a roomy, oversize T-shirt and call it a day—especially throughout this WFH period. They're inherently comfortable, cool, and easy to move around in (or hibernate in!) depending on your mood.

But figuring out how to wear an oversize T-shirt without looking sloppy and "undone” can often feel tricky. The last thing you want to do is look like you're about to go to bed (especially once we start getting out and about again). Here at Who What Wear, we fully live by the tenet that a little street style and Insta inspiration is all it takes to jump-start your imagination when it comes to trickier trends. Below we're sharing some cool tips, tricks, and outfit ideas to help you tackle the comfy-cool basic head-on so you can still feel comfortable and look stylish at the same time.

Tuck a loose tee into relaxed tailored pants for a casual-chic look.

Try an oversize graphic tee with a chic miniskirt and mules. Bonus if your colors contrast such as hot pink and lime green.

oversized t-shirt street style


Style du Monde

Add dimension by layering a fitted long sleeve-tee underneath a loose graphic tee. Finish by half-tucking your tee into relaxed fitting jeans.



Don't be afraid to mix prints. Wear an oversize vintage tee loosely over print pants and complete your ensemble with minimalist sandals.

Balance a large tee with tight leggings and pull the look together with an oversize blazer.

Play with layering techniques and try a baggy tee over a knit dress and under a crop top for a cool, fun look.

Bike shorts and an oversize tee are the perfect combo. Whether you wear the tee loose over the shorts or tucked in, give it a cool-girl touch by adding a gold chain belt around the waist. A pop of color will liven up the look.

oversized t-shirt street style


Sandra Semburg

Let a short hem peek out from underneath a long sleeve loose tee. Finish with chunky sneakers and tube socks.

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