Review: ‘The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’ “

The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’ by Bill Zehme

My rating: 3 of 5 stars

I have a complaint about the mostly amiable “The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’.” It has nothing to do with Bill Zehme’s occasionally purple prose, or the sometimes overly fawning tone, or the rambling organization.

It’s the layout.

Many years ago, when I lived in the New York area and took the train to work, there were people who would put on a pair of special gloves before opening their New York Times or Wall Street Journal. Why? They didn’t want to stain their hands with newsprint ink.

I wish the publishers of “The Way You Wear Your Hat” had thought of this.

The many chapters – “Pallies,” “Style,” “Broads” among them – begin with black pages laden with white print. There are also occasional lists and anecdotes (“His New Year’s Resolution Toasts,” “Francis Albert Sinatra Recalls His Debut on Earth”) also done in white-type-on-black. And that’s not to mention the type itself, which veers between frilly headings, random copperplate boldface, and pull quotes (aside from the standard text).

It’s infuriating to read. It feels like a jumbled scrapbook presented by your overly enthusiastic uncle. You just want him to take a deep breath and get his stories straight.

Too bad, because “The Way You Wear Your Hat” has some good stories. There’s a complete backgrounder of how the Rat Pack formed (it was mainly Humphrey Bogart’s doing; Sinatra inherited it, but preferred to call it “The Clan”), how fastidious Sinatra was in fashion (the precision of his cuffs, his fondness for Yardley’s English lavender soap and the color orange), how loyal he was to his friends. It’s fine, as far as it goes. It would have made a fine article, and in fact, that’s how it started.

However, as a book it’s too much of not much. Even in 1997, when it was published – not long before Sinatra’s death – Sinatra’s ways had vanished in a mist of cigarette smoke and Jack Daniel’s (two of his favorite things). His voice was still a precision instrument, his albums part of the pantheon, but though he may have been able to teach younger generations a thing or two about manners, he comes across no less a throwback than the beatniks and longhairs he disliked. After all, when’s the last time you heard a woman described as a “broad”?

Sinatra is one-third of Zehme’s “Trinity of Cool,” along with Johnny Carson and Hugh Hefner, and though all three have something to teach in their diffidence and style, all three also seem part of a vanished age, like black-and-white visitors to our HDTV universe. (Carson, whose wit is timeless, probably comes off as the most contemporary.)

Zehme is a fine and clever writer – he once did a story about Warren Beatty in which he timed Beatty’s prodigious pauses – but he lays his admiration for Sinatra on thick. This isn’t a biography – it’s more slices of life – but it still feels distinctly one-sided. There are gentle reminders of Sinatra’s vicious temper, but they’re heavily cushioned with stories of the singer’s generosity and (occasionally) remorse.

If you’re looking for a Sinatra biography – as I am, something fair-minded and comprehensive (in other words, not Kitty Kelley’s “His Way”) – you’ll want to go elsewhere. If you want a book to browse through, “The Way You Wear Your Hat” will fill the time with some nice anecdotes. If you want to lose yourself in some classic performances, there are any number of Sinatra LPs to pull up on your favorite streaming service (or, if you want to go old-school, to place on your hi-fi).

After all that, if you do pick up “The Way You Wear Your Hat,” you may want to reset the type. Frank wouldn’t like it if your fingers are blackened. He probably would have worn those newspaper gloves.

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