Larry Herrington has stood behind his barber chair in Ocoee for 50 years

When children walk into Larry’s Barber Shop for their first haircut, three things are guaranteed: They get their picture taken and can have it permanently taped onto the red-brick wall, they receive an official “Graduation to Manhood” certificate from Larry himself, and they get the cut on the house.

This is the way it has been for five decades — ever since Larry Herrington started working at the barber shop in the Ocoee Shopping Center, where Silver Star and Ocoee Apopka roads meet. The shopping center is one of the city’s oldest, and tucked somewhere near the middle is the nondescript storefront where Herrington has spent his days since graduating from barber college in 1968.

He initially worked at the shop, renting a barber’s chair from the owner, Willy Williams. When Williams retired about five years later, Herrington bought the establishment from him, renamed it and has operated it ever since.

Ocoee certainly was a smaller city 50 years ago, with a population of roughly 2,000.

“When I came here in 1968, a kid could walk by and I’d know who he was,” Herrington said. “A dog could walk by and I could tell you whose dog it was.

“When I came in here, Ocoee had four policemen (and) a volunteer fire department,” he said. “I used to know everybody, and now I don’t.”

Besides Herrington’s shop, the shopping strip boasted a Boogarts grocery store, Pounds Pharmacy, several clothing businesses, a jewelry, restaurant, laundromat and hardware store.

“Me and the laundromat are the only survivors,” the barber said. “I’ve seen this strip build up, and I’ve seen it go down. And I’ve seen it built up again.”

When Herrington got his start in the business, he said, costs were minimal: “A dollar and a quarter for a regular haircut and a dollar and a half for a flat top. And if you couldn’t cut a flat top at that time, you were out of business. I’ve seen (hairstyles) go from flat tops, to hair over the ears, to flat top ponytails. And now it’s back to regular haircuts and flattops.”

Those remain his specialty, and he said he has no desire to learn the different trending hairstyles.

“I don’t need to keep up with that anymore,” he said.

FROM SALUTES TO SCISSORS

Herrington, the oldest of seven children, was 11 when his family moved to Winter Garden from Alabama. After attending Lakeview High School, he joined the military like his father and four of his brothers.

Two years later, in 1967, he returned to Florida and attended a barber college in Orlando under the G.I. Bill. The owner was Jack Carter Sr., whose son, Jack Jr., currently operates a barber shop in Winter Garden.

He completed his schooling in nine months and began what would become his lifelong career at the Ocoee barber shop.

CUTTING FOR GENERATIONS

There are families who wouldn’t go anywhere else for their haircuts, some for four and five generations, including the family of Ocoee resident R.V. Henry.

“A … girl called me from New York and said, ‘Larry this is so-and-so, and we have a set of twin boys, and we want to come down in June and have you cut their hair.’ That makes six generations (on their father’s side), four on her side.”

One of his first customers, he said, was Lowell Boggs, who was a teacher. He still is cutting Boggs’ hair 50 years later.

He could be considered the Ocoee politicians’ barber, as he has used his clippers on former mayors Lester Dabbs and Scott Vandergrift and current Mayor Rusty Johnson.

“It’s always been like a family,” Herrington said. “First thing I ask new customers, ‘Where are you from? How many kids do you have? What kind of job do you do?’ And then we go from there. That’s how I treat these people — like family.”

No one makes an appointment; they simply show up.

As Herrington cuts, the barber and his customers talk shop, and the conversation, more times than not, gravitates toward local history.

“We talk about the old times and what it looked like then,” he said. “Mr. (Hartle) Bowness once said, ‘I used to sit outside my place at night, when everything was flat from here to Winter Garden, and I used to stay open until I saw the last light go out in Winter Garden because they might buy 15 cents worth of gas.”

The east wall of the barber shop is a testament to Herrington’s popularity. Taped to the red-brick wall are probably 100 faded yellow Polaroid photographs of first haircuts. Many of the young clients, such as Wilson Swope and the Sanders triplets, are teenagers and young men today.

When Polaroid cameras gave way to digital cameras and smart phones, many mothers printed their own photos and brought them back for Herrington’s wall of fame.

Framing the pictures are mounted fish, an old equestrian harness and other novelties given to him by friends.

Herrington is 75 and can’t stand as much as he used to, but he still manages to make a living at his barber shop, where he continues giving his customers a decent haircut, friendship and conversation.

“I have a place to come to and a place to talk,” he said. “I have guys who come in for a few minutes and talk, I have guys come in and play some music for a little bit. It’s changed because … we used to sit around and talk about fishing and hunting and girls and now we talk about surgeries and doctor’s appointments.”

Several guitars sit in the back room, ready to be strummed at a moment’s notice when a friend walks through the door and wants to play a few tunes.

“If you love what you’re doing, you’ll never work a day in your life,” Herrington said. “And that’s how it is with this shop.”

A GOLDEN CELEBRATION

To mark the momentous occasion of 50 years of service to the community, Herrington’s wife, Martha, and two daughters, Sandy Hendrix and Amy Lindsey, surprised him with a party at the shop.

On Saturday, June 23, the barber opened his doors that morning and started cutting hair. A little later, he noticed that many of those same customers were returning, as were dozens of other clients and their families.

Hendrix said he was overwhelmed by the turnout, which included his pastor, Jeff Prichard, as well as Ocoee Commissioner Rosemary Wilsen and Mayor Johnson, who presented a proclamation.

“It’s been a great 50 years,” Herrington said. “And I’ve enjoyed every minute of it. I just love people.”

After standing behind a barber chair for so long, many people would be discussing retirement. But not Herrington. Not yet.

“When I walk in here and it’s not fun anymore, then it’s time to go home,” he said.