Pillbox hats are back, and not in a quiet way. Alaïa, Chloé, Altuzarra, and Valentino all put versions on the runway this season, and by the time fall fashion week street style rolled around, the accessory had fully taken over, showing up in leather, velvet, fur, and the classic wool, worn by everyone from show-goers to Pamela Anderson to Elsa Hosk. The reference point is obviously Jackie Kennedy, and that’s exactly the problem and the appeal at the same time.
My honest take: pill hats are genuinely cute on some people and genuinely rough on most of us, and the difference has almost nothing to do with style and everything to do with face shape and hair volume. This is a hat that sits close to the head with no brim to soften anything, which means it needs either a strong jawline, a lot of hair working around it, or the kind of face that photographs well from every angle. On the right person it looks intentional, a little formal, a little theatrical in a good way. On the wrong person it reads like a flight attendant costume from a movie set in 1963.
I would not personally wear one. I’ve tried, standing in a dressing room mirror giving it an honest shot, and it just doesn’t do for my face what it does for, say, Pamela Anderson’s. She’s got the bone structure and the general sense of glamour-as-a-bit that makes a pillbox hat look like a wink rather than a costume. Elsa Hosk pulls it off for a similar reason: strong features, a lot of confidence, a face that can hold its own against a hat with that much presence.
The hat also asks a lot of the rest of the outfit. Because it’s so architectural, it wants a clean, considered look underneath it, not a busy one. The runway versions that worked best paired the hat with something simple, a coat, a tailored dress, minimal jewelry, letting the hat be the one loud thing.
I’d never buy one for myself, but I’ll happily watch other people wear them well. If your face can hold a hat with zero brim and full confidence, go for it, this is your season. If you’re not sure, that uncertainty is probably your answer.