It started with a love for loud, colorful shirts. Now, it’s turning heads for a very different reason.

In Chicago’s Beverly neighborhood, 23-year-old Nate Simon and his mom, Holly, have built a clothing brand that’s as bold in purpose as it is in style.

They call it 21 Pineapples.

The name carries meaning. The number 21 represents the extra chromosome people with Down syndrome have. The pineapple stands for warmth and welcome. Together, it’s a message you can wear.

“I started my own company because I love Hawaiian shirts,” Nate said to NBC 5 Chicago. “It’s all about love and kindness. I love it, because I love meeting new people. It is my favorite thing to do.”

What began as a simple idea has grown into something more personal for the family.

“Our kids can go to school here in Illinois till they’re 22,” Holly Simon said to NBC 5 Chicago. “When they age out, there’s nothing necessarily in place for them. So, we as parents have to come up with what’s next.”

For Nate, that “what’s next” came naturally.

“He was noticed on social media for his love for fashion, his drip,” she said. “So, we thought it was an easy segue.”

The brand quickly found its audience, drawn not just to the bright patterns but to Nate himself.

Holly is quick to point out that the story is bigger than a diagnosis.

“Nate’s Nate. He’s not Down syndrome,” she said. “Nate Simon is a 23-year-old man who likes to drink beer. He loves to eat, loves to make people laugh.”

And maybe that’s the point.

This isn’t about labels. It’s about personality, connection, and showing up as yourself.

For Nate, every shirt is a conversation starter. Every interaction is a chance to spread something simple.

“They’re hoping to change the world one funky shirt at a time.”

📸 Credit: NBC 5 Chicago