Chubbies Has Built a $100 Million Business With Irreverant, Everyday Man Merch

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The Chubbies brand got its start in shorts and has since expanded into swimwear, polos, pants and an NFL license.

It started out in 2011 as a side hustle for four friends from Stanford University who rebelled against “shirtless men with rippling ab muscles, some standing outside of storefronts coating you with cologne.”

Castillo said in its infancy, Chubbies created product for him and his friends. But now, that lens has been expanded to include a wide range of customers. “The mentality of the past is: hey, we’re really building product and gear for us, and now we’re really focused on this customer that we’ve fortunately nurtured over the course of the past decade, and have the ability to introduce new things to.

From there, the founders spent a number of years opening pop-ups in various places around the country learning about their customer and how to be retailers. But the company has managed to gain a foothold with younger men as well. Chubbies now offers boyswear because its customers started having children and would buy pieces for their sons in bright colors in the smallest sizes possible. “So we said, maybe there’s an opportunity here,” Castillo said.And it’s worked. “We’ve seen really good traction with that,” he said.

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