I’m going to go ahead and say it: You speak for us all with this question. And I’m not going to lie, it stumped me for a bit. Because I couldn’t, in good conscience, tell you to put on any ol’ pair of sneakers with your go-to sweats and call it a day.
But after doing a bit of Instagram stalking (after which I can confirm Hailey Bieber is the queen of making sweats look unbelievably cool) and some masked street stalking, too (I only got a few weird looks), I discovered one common thread among the cute looks. It’s all about highlighting the ankle! It sounds simple, but there’s something about a flash of skin (or sock) at the bottom of a loose, casual pant that makes this piece of loungewear feel more like a cool streetwear look and less like something tossed together from the dirty laundry pile.
However, it’s worth noting that this advice works with a pant that’s cinched at the ankle—and doubly so if said pant is slightly cropped to or right above the ankle. This ensures there’s no mess of fabric pooling above the shoe, creating a slightly more streamlined effect while offering plenty of opportunities for bypassers to peep at your purposely exposed ankle.
This leads us to the number-one most flattering kick to wear: the semi-clunky, vintage-inspired sneaker. Not quite a dad sneak, these are more of the technical kicks that are akin to a New Balance 990v5 ($175) or even the thick-soled Nike Air Force 1s ($110). To really maximize the effect and, make you look like Mrs. Beiber, you’ll want to acquire a pair of white tube socks ($15). Not into a statement sock? Try a retro-chic high-top sneaker, like the Reebok Lifestyle F/S Hi ($70) which will most definitely do the job of drawing attention to your lovely ankles.