top of page

One-woman show: Meet Maddy Pressley, the creator of Charlie and Claire's

All photos courtesy of Maddy Pressley.

When inspiration strikes Maddy Pressley, she needs to write it down right away, even if that means pulling off to the side of the road.

The 20-year-old University of Kentucky student is the owner and creator of Charlie and Claire’s, an online small business that creates colorful and comfortable graphic tees, hoodies and more. Catering to a growing 21,000 Instagram followers, Pressley uses her own experiences as a young woman to connect with her customers and give them the words of encouragement they may need to hear.

While ideas may not always hit her at the most convenient times, Pressley finds that this vulnerability is impactful when it comes to her business designs.

“I feel like I've kind of realized that a lot of the things I go through are just typical teenage girl things,” Pressley said. “So it's pretty applicable to a lot of people, like if I'm going through a heartbreak or a breakup, a lot of people are going to resonate with that.”

Through those difficult times, Pressley has been able to create some of her most popular collections. From hoodies with “dump him” and “you should block him” to self-love affirmations like “give yourself time” and “you are doing fine,” each handmade item is brightly colored with groovy, strategically-placed lettering.

While the young entrepreneur describes Charlie and Claire’s as a “dream come true,” the business almost didn’t happen at all.

“It was such an accident. I was 15 and my mom got me a Cricut for my birthday, and I looked her in the face and told her to take it back because I wanted clothes instead,” Pressley said.

Nevertheless, after being gifted the digital die cutting machine, she got to work on small projects like designing a quote to put on her journal or monogram letters to put on cups. While she says that she can't see herself producing those same kinds of designs today, they are what gained her original traction.

“People at school saw the cups and started asking if they could buy them from me. I would literally carry an extra little bag to school and hand-deliver people’s orders,” Pressley said.

From there, a business was born.

Hoping to follow in the footsteps of some of her biggest inspirations like Tori Gerbig, the creator of Pink Lily, and Diana Harbour, the founder of Red Dress Boutique, Pressley has moved from working solely out of her kitchen to opening her own office in Lexington.

“My biggest business advice is just to try it out, it's not going to hurt. Obviously, I had no idea whenever I was 15 and making water bottles that I would someday have an office, and, you know, maybe do this for the rest of my life. If I had never tried I would never know,” Pressley said.

While her apparel and the thoughtful design that goes into them can serve as inspiration for the thousands that buy from her shop, her impact can also be seen on those closest to her.

Pressley's younger sister Sophie modeling the "never been better" hoodie.

Pressley’s younger sister Sophie has been there the whole time to witness her sister’s business blossom from just an idea into what it is today. In the early days, she recounts the house being “filled with extreme excitement, happiness, and lots of creativity and crafts.”

“My sister is my biggest role model and has been for years. She is my best friend and is someone I genuinely want to be,” Sophie said. “My sister has helped me grow as a person in my happiness. She showed me what it's like to have true friends, love who you are and love your life.”

Pressley has big plans for her “one-woman show” and hopes to even open a brick-and-mortar location for Charlie and Claire’s in the future. You can shop her latest collections and newest arrivals at or visit her on Instagram at @charlieandclaires.


bottom of page