The other day, I asked a question on Instagram: ‘Are you a hat person?’ Surprisingly, most people made the same confession: “I love hats,” wrote New Englander Cheryl Sparks, “But I always feel so conspicuous.”

I get it, hats are intimating. Yet I have a theory: If you want be a hat person, you can be. You don’t need a certain sized head or the ‘persona’ we sometimes assume hat people have (They’re artistic! They’re outgoing! They don’t mind standing out!). You just have to believe you’re a hat person.

After all, Cup of Jo reader Madison said she always admired hat people but then had an epiphany: “One day, I just decided to become one. Once you wear hats regularly, others start believing you’re a hat person, too.”

If you want to make the jump, here are five hats to play around with:

Baseball Cap
The baseball cap is a gateway hat. Most people start wearing it to cover untamed hair while running errands. But then they catch themselves wearing one to meet friends at the park. And soon they’re wondering how it would look with a silk slip dress, even when their hair is freshly dried. You can take the relationship to the next level with a slogan cap: I wear a similar one, and this one-liner made me laugh. Or, if you’d prefer no catchphrase, this pastel number would go with everything.

Straw Hat
A straw hat is another excellent beginner style because it’s practical (hello, sun protection) but brings personality. Whenever I wear a floppy one, I feel like I should be cruising down Highway 1, admiring Big Sur’s cliffs and crashing waves.

Fisherman Cap
This fisherman cap provides face shade, but let’s be real, I don’t wear it for sun protection. I wear it because it makes me feel like a JLo backup dancer. You can pair this with a black turtleneck and houndstooth mini skirt for a Only Murders in the Building vibe. Or for a more relaxed feel, wear this olive number with a white T-shirt and jeans.

Bucket Hat
The first time I wore this bucket hat, my friend Angela laughed out loud. But I understood. Bucket hats are not designed to look good. Their revival is a playful trend, and I’m going to lean in hard on this 90’s-inspired fashion moment. If you’ve been itching to experiment with a bucket, this understated version would go with any outfit, and if you prefer prints, how sweet are these?

Beret
“Why are you posing like that? You’re so goofy!” my husband Max laughed when he took the photo above. Clearly, I’m not 100% confident wearing berets, yet this winter I am determined to fake it til I make it. If you’ve already mastered wearing these cuties, 1) I am truly jealous and 2) please share your styling tips. Ideally I’ll look more Parisian than Griswold. I’d love to incorporate a beret into my everyday winter uniform. And how pretty is this color?

What about you? Do you wear hats? I’m building up the courage to wear this one in the fall!

P.S. 15 baseball caps for every personality and “how I found my personal style.”

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