Frank Sinatra Nearly Attacked Writer Harlan Ellison Over a Pair of Shoes

When imagining Frank Sinatra, the image that comes to mind likely features him in a suit. The celebrity had meticulous standards for his wardrobe and appearance. He also liked others to adhere to his personal standards. When they didn’t, Sinatra got upset. Writer Harlan Ellison saw this firsthand when he and Sinatra nearly came to physical blows over a pair of boots.

A black and white picture of Harlan Ellison with his chin resting in his hand. Frank Sinatra wears a suit.
Harlan Ellison and Frank Sinatra | Denver Post via Getty Images; Bettmann/Contributor via Getty

Frank Sinatra was particular about appearances

Sinatra and his friends in the Rat Pack maintained stringent standards for their hygiene and appearance.

“Cleanliness was paramount to Dean [Martin] and Frank,” his friend Shirley MacLaine wrote in her book My Lucky Stars: A Hollywood Memoir, per Vanity Fair. “Whenever they took me with them for a little side trip to some gambling joints near Cincinnati, I’d sit in their hotel suite, fascinated by the spectacle of them primping for a night out.”

Sinatra showered multiple times a day and rarely wore anything but a suit.

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

Harlan Ellison’s shoes irritated Frank Sinatra

Sinatra was so strict about appearance that he got angry when others didn’t dress the way he liked. On one occasion, he was at a bar when he noticed Ellison. 

“[Ellison] wore a pair of brown corduroy slacks, a green shaggy-dog Shetland sweater, a tan suede jacket, and Game Warden boots, for which he had recently paid $60,” wrote Gay Talese in the article “Frank Sinatra Has a Cold,” per Creative Nonfiction.

Ellison’s outfit bothered Sinatra so much that he walked over to the writer as he played pool.

“Look, is there any reason why you’re talking to me?” Ellison asked.

“I don’t like the way you’re dressed,” Sinatra responded.

The conflict escalated until the two men were standing nose to nose, and Sinatra called Ellison’s not-yet-released movie The Oscar a “piece of crap.” Ellison backed down and left the room before things got physical, though. When he did, Sinatra told the bar manager that he didn’t want “anybody in here without coats and ties.”

Talese summed up the tense exchange.

“The whole thing had lasted only about three minutes. And three minutes after it was over, Frank Sinatra had probably forgotten about it for the rest of his life — as Ellison will probably remember it for the rest of his life.”

Harlan Ellison kept the shoes that upset Frank Sinatra

In 2013, Ellison admitted that he still had the shoes that caused Sinatra so much ire. He kept them preserved in a plastic bag in his closet.

“I was wearing light brown corduroy pants tucked all the way in and I was wearing a brown suede shirt, very Robin Hood–y with laces that went up the chest … very Carnaby Street,” he told Vulture. “I thought I looked very cool. I was getting laid regularly, and Frank Sinatra started in on me and it got very complex.”

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