This high school senior already has his own clothing line. His favorite rapper, Lil Baby, is a fan

PHILADELPHIA -- When Gavin Pennington was a middle schooler, he and his little brother had pictures of the rapper Lil Baby as their phone backgrounds, and posed with fake money acting like they were in one of his music videos. Now just a few years later, Lil Baby wears clothes that Pennington made.

“For him to just wear the clothes, it was just mind blowing. It was a full circle moment,” he said.

Pennington, a senior at St. Joe’s Prep in Philadelphia, is the founder of the upscale streetwear clothing brand, The Illest Club. Even though he started the brand just a year and a half ago, Illest Club has already exploded in popularity. Pennington, his family and friends have shipped the hoodies, sweatpants, T-shirts and other items out from the makeshift warehouse of his parents’ basement in Voorhees across the country, and as far as Europe and Australia.

The Illest Club even has the approval of the high fashion cognoscenti. Pennington, 18, debuted his clothes last month at Philly Fashion Week, with models working the runway in over a dozen Illest Club looks

“He stepped into it so fully and so committed and passionately. I don’t think there’s many people that would have done that and that’s what makes him special,” said Sonia Pennington, his mother.

Both of Pennington’s parents are entrepreneurs and own several businesses, including a dance studio, a restaurant and an outdoor events venue. They said that their son has had the same entrepreneurial spirit his whole life — when he was 8 years old, Pennington came home from school one day with a wad of cash. He told his parents that he was going to be selling shoes to his classmates now, and enlisted his mom to go shopping with him at Ross and TJ Maxx for nice sneakers on the cheap that he could flip.

“We were like, wait, we have to call parents,” Sonia said.

When he was older, Pennington made money cleaning and decorating his classmates’ shoes, and reselling popular clothing items. “He’s always wanted to create something and build something,” she said.

Sonia and her husband Damon have taught him entrepreneurial essentials as Illest Club has scaled up, like marketing and budgeting, but they’re impressed with the feel and savvy he already has for running a business.

“For us, I think it’s just so mind blowing because the things that we learned along the way, we see him in a lot of ways innately just picking up,” she said.

When Pennington told his family he was thinking of starting a clothing brand in August 2023, he had their full support. His little brother, Gabriel, even gave him some money to help launch the brand. Pennington made his first designs on his phone, and figured out the basics of the intricate world of manufacturing and sourcing materials through research and a willingness to make mistakes.

“I was going to make a way for it to work out,” he said.

Pennington said he’s always viewed The Illest Club as a brand defined by eye-catching embellishments and designs that make traditional streetwear pieces feel unique. The name is a reference to the inversion of the word “ill” from 80s and 90s hip-hop to describe something cool. Pennington said he liked the idea of bringing back something older and making it his own.

Illest Club’s aesthetic — of bold graphics and distressed materials — and its story have caught on so quickly that Pennington now sees other kids at school wearing his clothes every day. When Pennington and his St. Joe’s teammates played in the semifinals of the Philadelphia Catholic League last month, the student section filled up with kids wearing Illest Club.

Sometimes orders have gotten so overwhelming that Pennington has hired a fulfillment company to handle shipments and inventory. For his back to school collection this year, he received over 1,000 orders in just a few days.

The Illest Club’s next collection is out this month, with the drop of the new Virus #004 collection and a restock of some items from the Virus #003 collection, at theillestclub.com.

Even though he’s atop a growing business, Pennington said he plans to go to college next year, hopefully to Howard University. His parents have long stressed the importance of education to him and his brother. “You don’t ever want to sit in a room where everyone around you has more information about your business and they’re basically running it for you and telling you what to do,” Sonia said.

Illest Club will continue to evolve and expand, too. Currently, the clothes are sold in two stores — at Free Press, at 305 N. 15th Street in Philadelphia, and another in Ohio — but Pennington said he wants his clothes in stores around the country and the world.

“In a year and a half I’ve accomplished so much, but I only want to accomplish more,” he said.