Naples barbershop closing after 74 years on Fifth Avenue

Oliver’s Barbershop, a Naples icon on Fifth Avenue, faces an uncertain future after over 70 years in business.

The barbershop, passed down through generations, is being forced to close its doors. Matthew Cross, the current owner, shared his dismay at the situation.

“I’m supposed to just pack up and get my business done and everything out within three months and not make any money. I mean, I’m not. I’ll leave everything in this shop and just work until May 1 if I have to,” said Matthew Cross.

For Matthew Cross, this barbershop is more than just a business. His daughter, Ivy Cross, also spends her days there, painting and engaging with neighboring shops.

“I’m sad we’re never gonna see our shop in a few weeks,” said Ivy Cross, who is five years old.

The community is also mourning the barbershop’s loss. Robin Joy, an employee at Silver Eagle, expressed her sadness.

“They come because of him, not just because of the haircut,” said Joy. “It really is a whole different way of operating, and I’m heartbroken that he’s being pushed out by big business because that’s what’s happening to all of us, little guys.”

The barbershop’s closure comes at a difficult time for Matthew Cross, who recently lost his father, Oliver Cross. Despite the challenges, Matthew Cross remains hopeful.

“It’s going to be a rough, difficult transition. But they said everything happens for a reason, so one door closes and another one opens,” said Matthew Cross.

He is considering starting a mobile barbershop as his next venture.

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