CHICAGO, IL — In the heart of Chicago’s Beverly neighborhood, a local entrepreneur is proving that style isn’t just about what you wear—it’s about the soul you put into it. Nate Simon, a 23-year-old with a penchant for bold fashion and even bolder dreams, has turned his personal “drip” into 21 Pineapples, a clothing brand that is taking the Windy City by storm.
More Than Just a Shirt
The name “21 Pineapples” isn’t just a catchy title; it carries a deep personal significance. The 21 represents the extra chromosome shared by individuals with Down syndrome, while the pineapple serves as a universal symbol of sweetness and hospitality.
“I started my own company because I love Hawaiian shirts,” Nate Simon said. “It’s all about love and kindness. I love it, because I love meeting new people. It is my favorite thing to do.”
Bridging the ‘Age-Out’ Gap
For Nate’s mother and business partner, Holly Simon, the brand was born out of a necessity many families of children with disabilities face. In Illinois, students with special needs can remain in the school system until they are 22. After that, the path forward often becomes a “cliff” with few structured opportunities.
“When they age out, there’s nothing necessarily in place for them,” Holly explained. “So, we as parents have to come up with what’s next.”
Observing Nate’s natural flair for fashion and his growing social media presence, the transition to the apparel industry felt like a natural “segue.”
Redefining the Narrative
While the brand celebrates Nate’s journey, Holly is quick to point out that the business is about Nate the man, not a diagnosis.
“Nate’s Nate. He’s not Down syndrome,” Holly emphasized. “Nate Simon is a 23-year-old man who likes to drink beer. He loves to eat, loves to make people laugh.”
Join the Movement
What started as a local project has quickly evolved into a mission-driven brand that resonates far beyond the South Side. With every vibrant pattern and button-down, the duo is stitching together a community based on inclusion and, of course, impeccable style.
Local Impact: Are you rocking the 21 Pineapples look? Supporting local businesses like Nate’s helps create sustainable career paths for Chicagoans of all abilities.
