LOUISVILLE, Ky. — As 50 models walked down the runway at Fleur de Flea, Tyler Webb, also known as “Kentucky Boy Tyler,” watched his clothing collection displayed in style.


What You Need To Know

  • Tyler Webb is making luxury streetwear for celebrities, including Cardi B, John Mayer, and Louisville-native Jack Harlow 

  • The 25-year-old hosted his first fashion show, a feat he said is special because it allows his work to be displayed in its full effect

  • Webb felt pulled to host his first show in the state where his passion began

“First show, first runway show ever, here in Louisville, Kentucky, my home state,” Webb said excitedly. “I’m actually about to go sit in the audience and watch the show for the first time, so everything we’ve been working on, it will be my first time seeing it—I can’t wait!”

The Lexington native grew up interested in fashion and spent time designing, drawing and coming up with ideas. Now he’s making luxury streetwear for celebrities, including Cardi B, John Mayer and Louisville-native Jack Harlow. 

“As he got older, he got into sneakers and shoes and the different kinds. And he came to me one day, and he’s like, ‘I want to design shoes, that’s what I want to do,’” said Leeanna Webb, Tyler’s mother. “And so when it was time to look for what he was going to do after high school and stuff, I was like, let’s figure out the perfect fit.”

Following his mom’s support of his dreams, the 25-year-old hosted his first fashion show, a feat he says is special because it allows his work to be displayed in its full effect. 

You can watch the Louisville runway presentation above.

“Normally when I show my clothes off, it’s online. So it’s hard to get that full feeling of everything as a collection, the clothes being lived in, the movement of the clothes, the way a dress falls,” Tyler Webb said. “Like this is so important, it’s the full vision.”

Webb felt pulled to host his first show in the state where his passion began. 

“I really love Louisville’s creative scene right now,” Webb said. “I have a huge group of friends out here, so I’ve been living in LA the past couple years and I knew when I did my first runway show, I wanted it to be in Kentucky.”

He described the experience as beautiful, growing his love for the city where his roots are strong. 

“When he was growing up, he didn’t really have a role model in Lexington, especially. So I feel like he’s created a lot of his own way, and given the community and kids who follow him and stuff a good path to follow,” Leanna Webb said. 

Kentucky Boy Tyler, as he’s known online, said nobody should think it’s impossible to make it big in the arts if you’re from a small state like Kentucky.

“[A lot of people] feel discouraged trying to do artistic ventures, because people feel like they’re at an artistic disadvantage not being from [Los Angeles], not being from New York. It’s a longer fight, but, I mean, it’s certainly possible and you just got to go for it,” he said.  

Webb released his first collection, Piecemeal, in 2021. Last year, one of his creations was on display at the Metropolitan Museum of Art in New York City.