I Wear a Hat Every Day and Here’s Why You Should Too

It could result in you meeting Bruce Willis!

I Wear a Hat Every Day and Here’s Why You Should Too
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Lori Cheek, a self-professed hat-lover and founder of the dating app Cheekd, tells Best Life why she could never live without her extensive hat collection—and why everyone should turn to hats to boost their wardrobe and their sense of adventure. 

Lori Cheek wearing hats everyday

Lori Cheek wearing a favorite vintage felt fedora.

If you looked through my old photo albums, the first thing you’d probably notice is that I wear a lot of hats. Throughout the years, I’ll appear wearing my grandmother’s bonnets, my older brother’s baseball caps, and fun cowboy hats. Both of my grandmothers were fashionistas in their own right, and I’ve always been inspired by their style. Though they’ve both passed, I continue to wear some of their most fabulous accessories to this day.

As far as my wardrobe goes, hats are probably the thing I’ve invested most in throughout my life. A hat can dress up pretty much any outfit—and I often feel like an ensemble isn’t quite complete without one. I’ve got this crazy hair that sometimes gets a bit unruly, so I’ll often just pop on a hat and head out the door. 

About 10 years ago, I was walking through Soho when I spotted the most beautiful big black fur hat with a black bow inside the Emporio Armani store. The store had just closed and I remember thinking I didn’t care how much that hat cost—it had to be mine. It looked like it could have been straight out of Breakfast at Tiffany’s. The next morning I told my boss I was going to be late for work and I waited outside the store until it opened. Minutes later, that $1,600 hat was mine. It’s my favorite purchase of my life. People stop me on the street in that hat. I met Bruce Willis at a bar wearing that hat. (He sent me a bottle of champagne!) Hats like that one have sparked so many conversations with strangers and I’ve made several friends because of them. 

Lori Cheek wearing hats everyday

Lori wearing her Emporio Armani hat.

I found my other favorite hat seven years ago at a vintage store in Brooklyn. It’s a grey felt vintage fedora with a huge brown feather. I feel straight out of the 1940s when I wear this hat. When hats aren’t already as detailed as that one, I sometimes embellish them with pins, pom poms, gems, and feathers, to help them match my quirky style. 

I’m an entrepreneur and I live on a tight budget in New York City, but hats are the one thing I’ll splurge on. I can’t even house my entire collection at my apartment. I have nearly 100 vintage hats and three cowboy hats stored at my parents’ house in Kentucky and 20 in a storage facility in Brooklyn—and I’ve managed to strategically store about 50 in my apartment in New York.

Raised in Kentucky, I’ve always gone to the Kentucky Derby (my favorite day of the year) and for the past 16 years, I’ve hosted one of the biggest Kentucky Derby parties here in New York. Each year requires a new fabulous Derby hat and I always go full-out. I’ve even started making mini fascinators myself. 

Hats have given me such a sense of adventure over the years that I can’t recommend them enough. Besides covering up a bad hair day, they can transform any outfit—and maybe even your attitude—in a split second!

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