Keep It Moving | with Keola Rapozo
No handouts. No blueprint. Just movement.
That’s how Keola Rapozo built one of the most iconic clothing brands in Hawaiʻi—from a kid hustling in Kahalu’u to co-founding FITTED, a streetwear staple woven into the identity of the islands.
His story doesn’t shout. It doesn’t need to.
Because when you grow up with little, action becomes instinct. Not for the likes. Not for validation. But to survive. To build something that outlasts the struggle.
Keola and His Father
In the early ’80s, his family couldn’t afford a Christmas tree. So they cut one down themselves from the ridge in the back of Waiahole Valley. They even made their own ornaments—crafted from kamani nuts. Then they sold them at craft fairs across the islands to make ends meet.
“We’d show up the night before, set up our tent, set up our booth, and then sleep down there. The next morning we would set up our stuff and we’d open for business that weekend. And that’s how we survived in those early days.”
That’s where it started. Creating something from nothing. From watching his mom and stepdad craft by hand and hustle every weekend to make ends meet, Keola learned early:
Resourcefulness is its own kind of wealth.
While his friends were coasting, Keola was crafting. Inspired by music. By color. By design. He didn’t need approval, he needed to express something real. Even if it meant being misunderstood.
“My friends and people I grew up with was very template…I was into different stuff.”
Different isn’t easy. But it’s honest.
He didn’t fold to fit in. He leaned in. Fashion wasn’t just clothes, it was his medium. His language. His way of influencing without preaching.
“They’re like, what are you doing? You are getting a little crazy with the way you dress. I was wearing crazy colors… I remember wanting to influence my community through that. So my path became creating fashion.”
And that path wasn’t smooth. It was built on the quiet discipline most people don’t see. No glamorous startup story. Just couches and late nights.
At one of the lowest points in his life, broke, heartbroken, and sleeping on his sister’s couch after losing his mom, Keola kept moving.
He didn’t know exactly where he was headed, but he knew standing still wasn’t an option.
He was juggling three jobs: valet by day, graveyard shifts at the gas station, and an unpaid internship at Tori Richard squeezed in between.
All while going to school full-time.
His life wasn’t flashy. But it was focused. Most nights after 8 PM, instead of partying with his friends, he was alone at the gas station, pulling out rulers and patterns and practicing sewing.
“All I would do is my homework. I would make patterns and measure stuff.”
Even then, when others saw chaos, he built routine. He picked up a rule from a college librarian that changed his life: don’t leave campus without doing your assignment.
Focus. Finish. Move forward.
“That right there changed my entire outlook.”
No excuses, just progress. Every single day.
Soon came the call. An idea from a friend, former pro skater Rene Matthyssen.
“He said, you and me, we’re going to open one hat store.”
No money. No product. No plan. Just one small yes. One leap.
FITTED was born in the cracks of struggle. Bills unpaid. Phones disconnected. Ramen dinners. Clothes in trash bags. Still, he stayed in motion.
“We finally made enough money that both of us got our phone paid. That was a huge moment.”
But, it wasn’t about the phones. It was about the momentum. About proving that what they were building had weight.
Now, FITTED isn’t just fashion. It’s fabric. Of place. Of people. Of pride.
Keola designs in layers. Each piece has a purpose. Layered, intentional, and rooted in identity.
His deepest fear now?
“The day that I can’t create…is the day I am no longer useful. I’m so scared of that expiration date that I constantly have to keep moving forward.”
So he moves. Always forward. Always building. Not to chase relevance. But to stay alive in the work.
His advice to you: start with what you have. Stay in motion. And never let comfort replace purpose.
Enjoy Keola’s story? Check out our Instagram, @RISEHI for more inspiration from people who are designing their own path to success, or sign up for our newsletter to stay updated!