The Molehill

The Molehill

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The Molehill
how to become a hat person
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how to become a hat person

just wear one.

Viv Chen's avatar
Viv Chen
Sep 01, 2023
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The Molehill
The Molehill
how to become a hat person
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Happy September! A yearly subscription is on sale for $60 through Friday night. If you’re a monthly sub, this saves you the difference between a San Francisco latte ($8) and a Santa Fe latte ($5) every month ☕


One of the most common things I hear in fashion internet spaces is “I wish I could pull XYZ off.” I hear this most often in response to (1) haircuts and (2) hats. Something about stylistic choices to the head and the face feels high-stakes, doesn’t it? It’s the first thing we tend to notice about someone, and how we literally interface with another. I’m going to set haircuts aside (because that’s a whole other conversation) and focus on hats in this post.

In America there was a point when pretty much everyone wore hats; it was considered a default part of your outfit. Now, hats are by and large a stylistic accessory (save for practical applications like shade cover and warmth). For a history lesson, check out this piece— “How Cars and Hygiene Killed the Middle-Class Hat.”

I’m a firm believer that hats are underrated and under-utilized as a part of modern everyday fashion. It’s a shame that millinery is becoming a lost art.

Beyond baseball caps, beanies, and the pervasive Bay Area skullcap, I rarely see other types of hats out in the wild. I wanna see feathers! Fringe! So when I do, I always take note. Interesting headwear becomes an immediate fashion statement: it adds shape to your head and face, enhancing the overall “character-ness” of your presence.

All hats from Clyde, my favorite headwear designer.

And I believe anyone can pull off a hat. Being able to “pulling something off” is not based on your physical features, it’s about wearing it until you feel comfortable and confident in it. When you start dressing in ways that look “different” than the norm, people might notice at first and make a comment. If you hate being perceived, this part sucks. But honestly, I’ve found that after sticking with wearing that “different” thing…people get used to seeing you show up in unusual or eccentric ways. You wear the hat until one day you’re just a hat person, and they secretly wish they had the confidence to also be a hat person too.

If you’re hat-shy, I suggest starting with the following baby steps to incorporate head accessories into your outfits:

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