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 as I continue to WFH a few days a week. 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. 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.