There’s no reason to be modest about this: I look spectacular in a hat.
Hats occupy the uncanny valley of clothes: they have all the aspects of things one might put on one’s body (softish, cover something up, come in sizes), but a vast segment of the population feels somewhere between uneasy about and repulsed by the idea of actually integrating them into their lives. Whenever I venture out of the house wearing a hat, someone says, “I love your outfit! I wish I could pull that off!”
Can I tell you a secret? There’s no such thing as “pulling it off.” You don’t have to have amazing bone structure or a certain haircut or be between 18-22 or anything at all. The reason you think I look good in a hat is that it’s novel (if you don’t know me) or you’re used to seeing me in one (if you do).
When I was 15, I was at Dot Fox, talking to my style mentor Sally Bird (I know we’ve talked about Sally), and admiring this big, black felt hat. Since I was 15, I said something like, “I love this but I couldn’t ever wear it! I’d feel so silly about how weird I’d look because I am a teenager and think everyone is looking at me all the time and actually no one cares but I think they do.”
Sally said this: “You know what the trick to pulling it off is? You put that sucker on and don’t take it off until everyone is telling you how goddamn stunning you are.”