Lori Cheek’s custom hats put individuality ahead of trends
Lori Cheek is the Founder & Creative Director of Cheekd, a boutique hat brand making one-of-a-kind, custom-embellished hats with vintage details. In this conversation, Cheek explains how pop-ups and face-to-face customer reactions helped build the business, and why creative ambition needs to be balanced with costs and customer demand.
Put your work in front of real customers early and pay attention to their reactions. For a creative business, developing a distinct style also means watching costs and understanding what customers want.
What’s the short story of how your business started, and what makes it genuinely different from the other options your customers have?
I’ve always had a creative streak. I spent 16 years in architecture before jumping into the startup world, and I’ve always loved fashion, vintage treasures, and finding ways to make ordinary things extraordinary. CHEEKD grew out of that passion. I started transforming hats with vintage brooches, feathers, ribbons, and unexpected details, creating pieces that feel more like wearable art than everyday accessories. Alongside my signature hat collection, I also curate an eclectic mix of vintage fashion, jewelry, and accessories. What makes my business different is that I’m not interested in mass production or following every trend. I love discovering pieces with character and giving them a new life, whether that’s a one-of-a-kind hat or a fabulous vintage find.
How did you win your first customers, and where does most of your new business come from today?
I started by putting my designs out into the world at local pop-ups, markets, and events around Louisville and Southern Indiana. There’s something incredibly rewarding about watching someone try on one of my hats and immediately light up. Those face-to-face interactions helped me build my first customer base, and word of mouth has been huge. Today, I have more than 32 hats at Whiskey Thief Distillery in Frankfort, Kentucky, and also sell at Mood, a curated vintage and contemporary fashion boutique in downtown Jeffersonville, Indiana. A lot of my new business comes through pop-up events, local partnerships, social media, and people discovering my hats while they’re out enjoying themselves. I love that the business has grown so organically, one conversation and one hat at a time.
What’s one decision that changed the direction of your business, and one mistake that taught you the most?
One of the best decisions I made was getting out from behind a screen and selling my designs in person. After years in the tech world, I had forgotten how exciting it could be to connect with customers face-to-face and see their reactions in real time. It completely changed how I thought about growing the business. One lesson I’ve learned is that I can sometimes get carried away with the creative process. I love hunting for unusual pieces and experimenting with designs, but I’ve had to learn that running a creative business also means watching costs, understanding what customers actually want, and knowing when a design is finished. Sometimes less really is more.
What has changed in your industry or in what your customers expect over the last couple of years, and how have you adapted?
I think people are craving individuality more than ever. There’s so much mass-produced fashion out there, and customers are looking for pieces that have personality, tell a story, and don’t look like everything else on the shelf. I’ve also noticed how much people enjoy being part of the creative process. That’s why I’m expanding into custom designs and interactive hat bar experiences where customers can choose their own ribbons, feathers, and embellishments. It’s not just about buying a hat anymore. It’s about creating something personal and having fun doing it.
If you were advising someone starting out in your industry today, what would you tell them to do first, and what would you tell them to ignore?
Start creating, put your work in front of real people, and pay attention to their reactions. You don’t need a perfect website, a huge following, or an enormous budget to get started. Some of the best feedback I’ve received has come from simply showing up at an event and talking to customers. I’d tell people to ignore the pressure to look like a big, established brand right out of the gate. Focus on developing your own style instead of copying what’s already popular. And don’t underestimate the power of starting small. You never know what one customer, one event, or one unexpected opportunity might turn into.
Thank you to Lori Cheek and the team at Cheekd for sharing what actually worked with Leaders Perception readers.
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