If you’ve hung out in a cool part of town any time during the last two years, you’ve seen them: trendy men and women wearing trendy hats. No, not fedoras, or beanies, or baseball caps. I’m talking about those felt or straw hats with the stiff, wide-ish brim that every celebrity and generally cool person seemingly acquired overnight some time in 2013. As quickly as they appeared on the heads of famous folk, they started topping trendsetting normal peoples’ heads at dive bars, music festivals, and farm-to-table restaurants.

If you’re anything like me, the first time you saw a friend or acquaintance wearing one of the aforementioned hats, you thought to yourself – or maybe even said aloud – “I wish I could pull that off, but I can’t.” If that’s you, I’ve got good news for: you can pull it off, and I’ll tell you how.

Here are the steps to looking good in a trendy hat:

1. Pick up a hat

2. Put it on

No, I did not forget to add any additional steps. Yes, these are truly all the steps involved. Let me give some clarification… 

“I wish I could pull that off,” is something I used to say a lot. I spent most of my life so far thinking that there were two types of people in the world: people who can pull cool things off, and people who can’t. I, for the record, fell into the “people who can’t” camp. I could never pull off dancing – my body was too stiff and uncoordinated. I couldn’t pull off skirts – my legs were too muscular and bulky. I also couldn’t pull off talking to boys – the coy, flirty things Seventeen Magazine told me to say never felt natural coming from me. To top all of this off, it always seemed like my closest friends fell into the “people who can” camp. I always felt like the less funny, less pretty, less talented friend. Things that seemed natural for them never felt right for me.

For a long time, I allowed myself to not try things because they didn’t fit into this vision I had of myself. I was afraid that if I wore something I normally wouldn’t or said something that was even the slightest bit out of character, people would see right through me and know I was a fraud.

For me, I think that most of the reason I lived in the “people who can’t” camp was because of my staunch perception of myself. I believed I couldn’t dance, or wear skirts, or flirt, or wear hats, and so I couldn’t. But that’s really all that’s stopped me from doing what I wanted in life – my limits on myself.


 I bought one of those trendy hats after a while, and it sat in my closet unworn for weeks. I was nervous to wear it out in public, even though I thought I looked good in it. The first time I finally did gather the courage to wear my hat out of the confines of my house, I was prepared for judging stares or critical comments. Instead, the only comment I received was, “I wish I could pull that off.”

The trick to pulling something off is just doing it. The more you try things you’re uncomfortable about, the more confident you’ll become in yourself and your ability to experiment with your own definition of yourself. It’s hard and weird at first, but you’ll find that people don’t question your authenticity nearly as much as you do. 

One last tip: If you’re still nervous about wearing a trendy hat, or bright lipstick, or really short hair, or any trend, try it out in a place you don’t know anyone first. I’ve found that I’m most nervous that my friends and family will wonder why I’m wearing what I’m wearing or doing what I’m doing. It’s easier to explore a new style or activity who don’t have any previous notion of you for comparison. Take your trend out to a local coffee shop or store, and I bet you’ll be pleasantly surprised how little people worry about what you’re wearing.