When Jim Dolloff was 2 years old, his mother, Marilyn, decided he was ready for his first haircut. She told her husband, Alan, to take their son to the barbershop.

Alan Dolloff has followed that order for 50 years.

“I do exactly what my wife tells me,” he said.

Alan, 80, and Jim, now 52, have gotten every haircut together for five decades.

As a boy, Jim tagged along to the barbershop with his dad. Later, when he married and moved to South Portland, the pair would meet for their regular appointment. Several years ago, Jim and his wife moved into an apartment attached to the Baldwin farmhouse passed down through generations of Marilyn’s family, where Alan and Marilyn raised their children and still live. So when the father and son decided this spring that they needed a trim, they made plans to drive together to Cuttin’ It Close in Standish.

“It’s just something we can do together,” Jim said.


Alan met Marilyn as a teenager at Potter Academy in Sebago. They married when he returned to Maine from the Air Force. They had a daughter and, three years later, Jim was born. Alan calls him “a mama’s boy.”

“When he was born, you couldn’t get her away from him,” Alan said. “It’s been that way ever since.”

Jim’s first haircut was at a barbershop in Brownfield. Alan worried the toddler would cry or fuss, but he sat calmly in the chair.

“He took it home and showed it to his mother as proud as he could be,” Alan said.

Alan taught automotive technology at Westbrook High School for more than 20 years, while his wife ran a bake shop out of the farmhouse for a time. The kids graduated from Sacopee Valley High School. The Dolloffs took road trips together in Maine and, once, to Disneyland in California. Jim hunted and fished with his father and uncle. Both children started their own families in Maine not far from where they grew up.

Leanne Jackson, left, and Donna Kenison, reflected in a mirror, give simultaneous haircuts to Alan and Jim Dolloff.

Over the years, Jim and Alan have frequented a handful of barbershops. After the Brownfield shop, they went to a man Alan dubbed “the hippie barber” in Bridgton for a few years. Then there was the barber who learned how to cut hair in prison and always trimmed too short. They found a father-daughter team they liked for nearly 20 years, but when the woman moved her business to her home a couple years ago, the Dolloffs lost contact with her. When Jim’s sister Lori attended beauty school in her 20s, they offered to be her test subjects.


“Once,” Jim said.

“Only once,” Alan said.

“That’s the worst one we ever had,” Jim said.

“I didn’t say that,” Alan said with a smile.

The Dolloffs were looking for a new shop a couple years ago when Jim spied the red, white and blue “BARBER” banner flapping on the side of Route 25 in Standish.

Allan Dolloff sits in a barber chair while cosmetologist Donna Kenison prepares to cut his hair.

Since then, they’ve been regulars at Cuttin’ It Close. On a brisk April morning, they are the first customers of the day for owners Donna Kenison and Leanne Jackson.


They settle into two chairs on opposite sides of a mirror. Jackson fastens red cape around Jim’s shoulders.

“You want me to cut it how we have been?” Jackson asks Jim. “A little shorter on the sides?”

“Yeah,” he says.

While the father and son share tastes in food (steak) and politics (Republican), they diverge on hairstyle. Alan’s hair settles flat on his head, while Jim’s bristles straight up.

Jim Dolloff,sits while cosmetologist Leanne Jackson wets his hair.

“During the teenage years, I didn’t want the boy’s haircut anymore,” Jim says. “I wanted my hair longer, but he said, ‘You can’t have your hair long, you hippie.'”

They compromised, and Jim kept his hair trimmed below the ears as a young man. Alan’s cut has remained consistent, though one barber gently nudged him to get rid of his combover a few years ago.


“Everybody knew I was getting bald,” Alan says.

Kenison uses scissors on Alan’s hair, while Jackson pulls out an electric razor. The mirror is between Alan and Jim, but they still banter back and forth. Alan tells Kenison about a citizenship award he was soon to receive when Jim interrupts.

“See, I told you he likes to brag,” the son jokes.

“Well you’ve got to have something to brag about,” his father quips.

In addition to his work as a teacher, Alan served decades on the board of selectmen in Baldwin and maintained all the cemeteries in town. He was also part of the town’s fire department and served as chief for 20 years. He’s quick to point out that Jim is following in those footsteps.

Jim Dolloff sits while Leanne Jackson wields the clippers.

His son, who makes coffee extracts for Kerry Ingredients in Portland, has taken his father’s place on the fire department. Jim hopes to run for his father’s old seat on the select board as well.


“These things we do together,” Alan says.

Jim’s cut finishes first, and Jackson uses a hairdryer to blow the short clippings from his shoulders. She hands him his glasses – square lenses with no frames. He puts them on and leans into the mirror.

“Perfect,” he says.

As Jim stands and reaches for his wallet, Kenison uses her hairdryer to send the short hairs on Alan’s shoulders to the floor. She hands him his glasses – larger with round lenses and gold rims. Like his son, he puts them on and leans into the mirror.

“There we go,” Alan says.

The Dolloffs talk with the stylists about the upcoming mud season and the sap they would collect that afternoon. Alan still cuts logs and hay on the 150 acres where they live.


“He’s a hard worker,” Jim says. “He does it by himself, because he doesn’t want anybody else helping him.”

They pay for their haircuts but don’t schedule a follow-up. Instead, they will call in three months or so, when one will look at the other and suggest a trim.

“He’s not only my son, but he’s my best friend,” Alan says as the pair chat afterward.

“I thought Ronny was,” Jim replies with a little smile.

“No, he isn’t,” Alan says mildly. “You are.”

Megan Doyle can be contacted at 791-6327 or at:


Twitter: megan_e_doyle

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