Frank Sinatra was known for his impeccable appearance, and his friends say he had strict standards when it came to how he looked.

He always wore suits that were tailored to perfection, was diligent about personal hygiene, and made sure his hair always looked neat and well-groomed. However, as his hair began to thin, he had to resort to toupees.

He had a collection of hairpieces at home, but he also wanted to make sure he always had extras on hand.

To ensure this, Sinatra hired a woman to carry his hairpieces around for him, and he paid her very well for this job.

According to Shirley MacLaine, Sinatra’s friend, Sinatra was very particular about his appearance.

Even though he was known for staying up late drinking and gambling, he never wanted to look like he had.

MacLaine wrote in her memoir, “My Lucky Stars: A Hollywood Memoir”, “They splashed on their cologne, each dousing himself with his favorite brand (Fabergé’s Woodhue for Dean). Their white shirts were crisp and new, the ties well chosen, the suits expensive and impeccably tailored.”

She also questioned why people like Sinatra were so obsessed with cleanliness, “Why was it that they who consorted with gangster types and worked hard at entertaining people insisted on being perceived as so clean? It was a fundamental obsession with them and one that endlessly fascinated me.”

To make sure he always had a hairpiece on hand, Sinatra hired a woman named Helen Turpin to carry around roughly 30 of his hairpieces in a bag for him.

Gay Talese, wrote in an article for “Creative Nonfiction”, “He also wore, as everybody seemed to know, a remarkably convincing black hairpiece, one of 60 that he owns, most of them under the care of an inconspicuous little gray-haired lady who, holding his hair in a tiny satchel, follows him around whenever he performs.

She earns $400 a week.” Talese also provided more information about Turpin in a letter to The Atlantic, “I was astonished to hear that Sinatra had such an employee, and she replied that she’d been doing the job for three years, and that he paid her $80 a day, and it ended up being on average $400 week, or about twenty grand a year — not a bad living, she added, since it consisted of nothing more arduous than carrying 30 or so hairpieces around in her satchel.”

“She let me peek into the satchel, and she added that Sinatra himself had another 30 hairpieces that he himself kept for use when she was not around.”

Turpin accompanied Sinatra to most professional venues, including movie sets, concerts, and nightclubs. To put it in perspective, $20,000 in 1965, when Talese met Turpin, roughly equates to $180,000 in 2022.

Despite the fact that Sinatra paid well for the safe transport of his hairpieces, those who knew him said the quality of his toupees declined over time.

Jerry Roman, who worked on Sinatra’s hair for The Manchurian Candidate, said, “He used to have some exceptionally good hairpieces. But later on he got very sloppy. In his last five years he went into a synthetic piece which really did not look very natural.”