In a world filled with off-the-shoulder tops, cropped turtlenecks, and wide-leg jeans, a beanie seems like the easiest thing to style: You put it on your head. But as evidenced by a friend who seemed truly perplexed recently—“I just don’t know where it should sit on my head or if it should flop over or stick straight up” is an actual, verbatim complaint she texted me recently—it’s not always that simple.
You may thing you’re just not a hat person, but you’d be wrong: Literally everyone, no matter your hairstyle or head shape, can pull off a beanie. It’s just about finding the right one: while we’d never deprive anyone of the newly on-trend pom pom beanie, long faces are better off with something a bit chunkier, and round faces can pull off something tighter. To prove our point, we found 26 models, bloggers, editors, and other stylish folk wearing the winter essential, as well as a similar style to shop.