Topping Off
The Return of Sinatra's Classic Hat, the Fedora
It should look easy, natural, casual.

It may not be entirely accurate to say that clothes make the man, but any Sinatra fan knows that they can showcase the man in a pretty elegant wrapper. And any good wrap job, of course, needs a good bow on top-which is to say, the right hat.

For Sinatra, particularly late in his life, that hat was occasionally a baseball cap. But that's not the topper we associate with him, the lid that became one of his trademarks as it adorned all those classic album covers. The classic Sinatra hat is the fedora. And in many ways, the fedora-the hat that Sinatra made as personal and stylish a signature as authoritative but conversational singing and an immaculate pocket square-is back.

Justin Timberlake wears one even when he's playing golf. Oscar nominee Terence Howard dresses up a pinstriped suit with an impeccable black felt job. British rocker Pete Doherty, often as not a mess in other ways, nonetheless makes a floppy fedora his sartorial trademark. And from the egregious fashion file, The Hills' Audrina Patridge was snapped by the paparazzi frolicking in an L.A. pool not long ago, surrounded by twentysomething lounge lizards whose idea of high fashion was sporting stingy-brimmed fedoras along with their baggy board shorts and abundant tattoos.

This summer, one of the most celebrated hats in film returned in Indiana Jones and the Temple of the Crystal Skull, complete with a moment in which Harrison Ford's young sidekick, Shia LeBeouf, tried to pick up Indy's battered fedora (and by doing so assume the mantle of the adventurer). Some of the theaters showing that film preceded it with a teaser trailer for The Spirit, a film noir from Sin City and 300 creator Frank Miller; the trailer focused on a few iconic images to define its hero - including, almost inevitably given the genre, a dark fedora pulled low.

Not all of these would please Sinatra. Indiana Jones' battered fedora, after all, is far rougher than Sinatra's impeccable felt Cavanaughs. And few of the new crop of fedora-wearers are worth emulating, at least if you're interested in Sinatra Style.

But the hat, no doubt, still packs a fashion punch. "Donning a fedora puts you in touch with a truly luminous and manly heritage," declared the Art of Manliness website, which calls itself "a blog dedicated to uncovering the lost art of being a man." The classic black fedora, said Edie Orenstein, owner of the trendsetting hat store Edie's Hats on Vancouver's Granville Island, is for "all ages, both sexes and all demographics" - and, she added late last year, the fall of 2007 was the moment when that hat returned with a vengeance.

Before we go further, a note on terms. The classic fedora, the kind sported by Sinatra on album covers ranging from Songs for Swingin' Lovers to Duets, dates back to the late 19th Century; it's generally made of soft felt, usually in black, gray or brown, creased lengthwise on top and pinched in front on both sides.

The variants frequently seen these days, with shorter brims than the classic fedora and a variety of patterns and prints, are often referred to by the British term trilby. Some sources insist that trilby and fedora are essentially synonyms, but for our purposes we'll posit that a fedora is the kind of broader-brimmed hat Sinatra would have worn; a trilby is smaller and trendier, the kind of lid that occupies acres of self space in every Urban Outfitters store these days.

To wear the hat with true Sinatra Style takes some doing. "No one wore a hat like Dad did," Tina Sinatra told Bill Zehme when he was writing The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin', a book well aware that if you want to sum up Sinatra style, you should start at the top.

The trick for newcomers, perhaps, is to make the fedora seem current rather than nostalgic. After all, Sinatra didn't wear one because Bogart had worn one in Casablanca. He wore one because he could tilt it to suit his mood or top any outfit.

Some current acolytes know how to make it work; others don't. When Justin Timberlake is in a vest, with his tie loosely knotted and a black hat tilted just so, he can get away with the look - but when he's on the golf course, the lid can look downright goofy. Jeremy Piven in t-shirt, blazer and a floppy black fedora with a big leather hatband looks like a low-rent pimp; if Brad Pitt occasionally gets away with pairing a t-shirt and fedora, it's mostly because he's Brad Pitt. The singer Usher, on the other hand, can wear a white fedora with a black jacket (something Sinatra would never have done) and make it look right.

Maybe it's silly to insist on fashion rules these days, so we'll just call these guidelines. If you want to carry off a fedora with even an inkling of Sinatra Style, it's best to remember a few things:

Wear it proudly, not ironically. It shouldn't look like a costume, or a pose. It should look easy, natural, casual.

If your head is stylish and the rest of you is rumpled, it's not going to work. A little striped trilby might work with jeans and a t-shirt; a more substantial fedora requires you to show some style below the neck, too.

Remember the old rules. Take it off when you go indoors: lobbies and large public spaces might be acceptable, but private homes and restaurants are not. Don't wear it during a meal. And never, ever (we're talking to you, friends of Audrina Patridge) wear it in the swimming pool.

When in doubt about how to tilt, follow Sinatra's lead. When you push it back and show more forehead, you're showing vulnerability. Pull it down, always with a tilt toward the right eyebrow, and you're darker and more debonair.

Sometimes, it really does come down to the way you wear your hat.

 

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