Annelli, who runs Gino's Barber Shop, with his son Michael, in Ossining at 7 Pleasantville Road, is planning on retiring soon.
A Cortlandt resident, Annelli said he has cut some customer's hair for more than 40 years. Parents have brought their children to get haircuts and those children eventually have brought children of their own. Annelli even cut the hair of John Cheever.
The barber came to Ossining from Bire, Italy when he was 16. He worked in Briarcliff before opening up his own shop on Spring Street in Ossining. He also worked in a barbershop at the Arcadian Shopping Center. He has been in his current location since 1981.
"I've seen a lot of changes," Annelli said. "From different hairstyles to different people."
Making his customers look good is Annelli's number one goal. He said with every customer he takes his time and makes sure he does a professional job.
"I treat my customers the way I would want to be treated," Annelli said. "I treat them with respect."
Annelli said he likes to get new customers to prove himself but he also values the generations of families that have come into his shop.
Many changes have occurred in the 59 years, Annelli has been in Ossining. Haircuts that used to cost $2 now cost $20. Rent was once $80 a month and now it runs $1,500.
When he first started in Ossining, Annelli said people who were born and raised in Ossining would stay in town, but now people move all over, often due to the high cost of living.
"I used to have customers for 10 to 20 years," Annelli said. "Now it's for four to five years and I don't see them anymore."
Annelli hopes to eventually move to Florida and wants to spend time more time with his wife, four kids and 12 grandchildren. He said he will miss his customers the most.
"I enjoyed talking to my customers and finding out what their hobbies are," Annelli said. "I like to get to know them and listen to what they have to say."
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