The Way He Wore his Hat

The Way He Wore his Hat

POSTED: May 17, 1998

The singer leans against a building, a gray snap-brim cocked high on his crown. A matching handkerchief is stuffed effortlessly in the breast pocket of his suit coat. The coat is black, of course, not brown. The tie is pulled loose and unashamedly lavender. The smoke from a Chesterfield curls toward a street lamp on a deserted corner. The singer’s eyes are downcast. Love’s gone, or at least gone wrong.

That pose, on the cover of Frank Sinatra’s first 12-inch album, In the Wee Small Hours, is more than 40 years old now. To this day, young men walk into Dietz’s hat store on South Street with photographs of the world-weary kid from Hoboken, N.J., hoping to duplicate The Look.

What Sinatra left with his death Thursday night was a legacy not only of song stylings, but of personal artistry.

He had a code of behavior with its own vocabulary – a tight, somewhat threatening world of pallies and Harveys, gassers and bunters. You were in or you were out. Most were out, but if you were in, you were golden.

Sinatra didn’t suffer tightwads or teetotalers. He duked the maitre d’ on the way out, not the way in, with a couple of big bills folded thrice into small squares. He called his Jack Daniel’s gasoline and was so single-handedly important to the distillery’s fortunes that it gave him an acre of sacred soil in Lynchburg, Tenn. He liked his Jack easy: three or four ice cubes, then two fingers of gas, finished with tap water. The flavors needed time to mix and chill. The glass was important, too. A squat old-fashioned glass pleased him. Nothing towering.

Two years ago, Esquire magazine senior writer Bill Zehme cataloged the elements of Sinatra style in a profile called “And Then There Was One.” Zehme didn’t want all the singer had learned about living to die with him.

“Men had gone soft and needed help, needed a Leader, needed Frank Sinatra,” Zehme wrote.“I wanted to ask him essential questions, the kind that could save a guy’s life. I wanted what might approximate Frank’s rules of order.” In December, Zehme expanded those rules into a full-length book, called The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’.

Sinatra’s rules were his own. The man who owned 60 toupees never had a plastic surgeon fix the scars he bore on the left side of his neck, the results of a crude forceps delivery. “People have suggested to me I ought to hide those scars, but no,” Sinatra once said. “They’re there, and that’s that. Why bother?”

He swore like a stevedore, once calling the women of the Australian press “buck-and-a-half hookers,” but decked a press agent for referring to Judy Garland as a “broad.” He went out of his way to make a lady comfortable. Once, Gay Talese wrote in his classic 1966 profile “Frank Sinatra Has a Cold,” a Life reporter named Jane Hoag, who had gone to school with the singer’s daughter Nancy, accidentally knocked over an alabaster bird during a party in the home of the first Mrs. Sinatra.

“Oh, that was one of mother’s favorite . . . ” Nancy began, and before she could finish the thought, her father glared at her and walked over to the remaining alabaster bird, knocking it off the table, too. He put his arm around the young woman, telling her, “That’s OK, kid.”

He loved some of the world’s most beautiful women, but he didn’t like them to smoke, yawn, wear too much perfume, dress too casually or show too much cleavage. Mia Farrow said he was a gentle hand-holder.

To the hated press in 1965, he said, “If I had as many love affairs as you have given me credit for, I would now be speaking to you from a jar at the Harvard Medical School.”

And how did he wear his hat? Many ways. He played the angles, the higher the brim, the more vulnerable the effect. “The hat was his crown, cocked askew, as defiant as he was,” Zehme wrote in last year’s book.

Sinatra had a snap-brim for all seasons, each made by Cavanaugh. A black or gray felt would do for cool breezes. Palmettos and straws with wide, pastel bands were right for the tropics. Nancy Sinatra told Zehme that her father wore them to hide his hairline, which began heading north when he was in his late 20s.

The way he put it on was a two-handed maneuver, curling the back brim up and tugging the front down, usually a couple of inches above his right brow. There’s a portrait on the back of Zehme’s book that shows the Sinatra of the ’50s walking away from the camera in a snap-brim and raincoat, down a graceless hallway. The hat is tilted rakishly, toward 4 o’clock. That would be 4 a.m., in the wee small hours, when he was often restless and demanding company.

A new doctor once asked him how much he drank. About 36 drinks a day, Sinatra figured, measuring out a fifth of Jack Daniel’s into rounds. The doctor wondered how he felt in the mornings.

“I don’t know,” Sinatra responded. “I’m never up in the morning, and I’m not sure you’re the doctor for me.”

He and his pallies had their own way of talking – it might as well have been Chinese to the uninitiated, a Rat Pack observer told Zehme.

Sinatra once slowed down to translate a few phrases for columnist Art Buchwald. In addition to Jack Daniel’s, gas was a good situation, and a gasser was someone who got things moving. The opposite of a gasser was a bunter. A Harvey was the sort of square who would walk into a French restaurant and ask, `What’s ready?” He could be a Clyde, too – someone from Dullsville, soon to be exiled to Scramsville, on the outskirts of Endsville.

A happening affair was Mothery, leading to the pairing of couples at Ring-a-Ding-Ding time for, if fortunate, a Little Hey-Hey. A bird was, well, the essential equipment, male and female. After nearly drowning in Hawaii in 1964, Sinatra explained simply, “Oh, I just got a little water on my bird, that’s all.”

He was one rare bird himself.


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