if you must

10 Hats That Won’t Make Me Cringe

Carrie Bradshaw, in a hat that does make me cringe. Photo: HBO

Hats mortify me. Not my hats — I don’t have hats. Your hats. Often, walking around New York, a city with a lot of looks and therefore a lot of hats, I am struck with the sudden urge to lie down with my hands over my eyes: That’s because your fedora is giving me a mean case of secondhand embarrassment.

I don’t believe you should wear newsboy caps or driving caps or Panama hats or bowler hats, ever. I just found out what a fiddler cap is, and I don’t want you to wear one. Don’t wear slouchy beanies that scrunch up in the back, especially if you’re wearing it indoors with a henley and no coat. Don’t wear beanies that sit on the tip-top of your head like a condom: I won’t be able to stand it.

Utility hats are fine. If it’s sunny, wear a baseball cap. If it’s cold, wear a beanie. If you’re fishing, wear a hiker hat. And if you must wear a hat for fashion — well, I decided to try to find ten hats that I thought you could wear without looking like the kind of person who wears a hat. Searching was terrible for me; there were so many bad hats. But between them, I found three hat categories that made me think, Okay, these hats are fine, you can wear them. Bucket hats (a twofer, they fall under both gorpcore and normcore), floppy beach hats (seen in French films), and berets (ditto, plus they’re on trend). Here are ten hats you should feel free to wear.

Bucket Hats


A cheerful bucket hat. Wear it with a hoodie!

Clyde Bucket Hat in Smoke Vinyl

I think this rain hat might be extremely cool.

Champion Reversible Mesh Bucket Hat

A very ’90s hat is a good way to get in on our very ’90s moment.

Baseball Caps

Cotton & Linen Baseball Cap

An upgraded baseball hat.

Rag & Bone Marilyn Baseball Cap

I think this Burberry-esque hat would look cool with a trench.

Nike Women’s H86 Swoosh Hat

For a (literally) head-to-toe athleisure look.

Sun Hats

Helen Kaminski Tahani Crochet Raffia Hat

This is a perfect little sun hat.

Floppy Straw Look Hat

Cheap and pretty.

Reversible Sunhat

Charming and stripy.


Helene Berman Basic Wool Beret

And last but not least, the only beret you’ll ever need.

The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best women’s jeans, rolling luggage, pillows for side sleepers, ultra-flattering pants, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.

Every editorial product is independently selected. If you buy something through our links, New York may earn an affiliate commission.

10 Hats That Won’t Make Me Cringe