We hear a lot about cool: this was where it began

As a singer, Frank Sinatra set the standard by which all others are judged. The same was true of his style

TWO MEN are sitting at a bar. Both are drinking bourbon, both are wearing suits. One looks hot and hassled in a creased shirt and crooked tie. The other? He just looks cool.

Some men are like that, they stand out in a crowded room. This one doesn't care about his liver, his lungs or his lover: as the ice melts in his drink and a curl of smoke rises to the ceiling, his eyes glitter with an arrogance that dares any female to approach.

Men like him should only be photo- graphed in black and white. Partly because they're so old-fashioned, and partly because they would love it. Monochrome portraits have a glamour that is both nostalgic and timeless; flattering our barfly with one would make explicit the link with his role model, the young Frank.

Death will do nothing to destroy the mythology that has built up around the boy from Hoboken, any more than did his growing old in disgrace. For 40 years he has been a fantasy figure, remaining for ever young and sharp in the minds of more men than would dare to admit it. Which men among us would pass up the chance to be the hard-drinking, hard-loving bastard that Sinatra was when he hung out with Dean Martin and the rest of the Rat Pack. Not for life, you understand. Just until the hangover kicked in.

"You cannot but admire Frank Sinatra. Whatever else, he had a lot of style." The words, echoed by many this weekend, come from an unlikely source: a young black man with a reputation for being at the sharp end of modern design. But Ozwald Boateng knows when a man looks good. "Even though Sinatra seems old hat, his influence endures," says Boateng. A suit is a social uniform, a formal construction that can hide a personality, but Sinatra was a short man, not conventionally attractive, who showed that the style or cut of the cloth counted for less than how you filled it.

Or how you subverted it, as modern designers seek to do now, and as Sinatra did back then, when the rules were more rigid. "When you watch his films he looks good even when he's drunk. He is comfortable no matter how formally he is dressed. He is one of the best wearers of a suit ever."

A photograph of Sinatra in his prime is a universal shorthand for male cool. Go into any bachelor pad and you can tell whether the owner is a man or a boy instantly, by looking at the pictures on the wall. If James Dean is still walking down the boulevard of broken dreams, expect adolescent petulance. If Frank is smiling down at you, however, the entertainment will be adult. He's there in every new drinking den that knows its iconography, a symbol of reassurance like the Pope in a Catholic home. Everybody knows what it means: you can even see the image of this Italian-American in the London dressing rooms of the French designer Agnes B.

So where does it come from, this mythical status? The cultural commentator Peter York believes it can be traced back to Sinatra's sessions for Capitol Records in the mid-Fifties and the way they were packaged. "The cover of the album Songs for Swinging Lovers showed Frank with a snappy hat and a coat fingered over his back, and was proto-mod. By which I mean it was a popular distillation of all that was cool about Italy, America, jazz and so on, in a way that was much more accessible than the originals."

Vespa scooters are fashionable again, and you can't walk down the street without passing an espresso bar. Classic Italian design endures, and so does our fascination with America. Youth culture fades away but Sinatra's image still supersedes issues of age and class, four decades later. His music was forced out of the charts by rock'n'roll during the Sixties, but he was the king of cool to the mods, who took the Italian influence further with their suited and booted look.

In the decade that followed very few people looked to Sinatra for style, except perhaps Bryan Ferry, the flamboyant lead singer of Roxy Music who wore suits and uniforms when everyone else was in flares. If the version of "My Way" recorded by Sid Vicious meant anything it was a deserved attack on the bloated self-indulgence of a song that can only be sung without embarrassment if one is blind drunk.

It was after punk that Sinatra was thought cool again, as shops like American Classics encouraged a new take on the Fifties look. His name was borrowed by the pop group Frankie Goes To Hollywood and his image by Harry Connick Jr. As men were allowed to be dandies, so they redis- covered the suit and its accessories, from cufflinks and ties to hats and brogues. "If you want to dress that way you can aspire no higher than to look like Frank Sinatra," says Dylan Jones, the commentator who played an enthusiastic part in the rebirth of British style culture at that time. "He was a fantasy figure. There was nothing remotely British about the way he looked."

But the appeal of Sinatra is not about fashion. The Beatles offered mop- tops and the Sex Pistols suggested safety-pins, but neither are seen much these days. The lasting appeal of Sinatra is about what John Lennon had but Paul McCartney didn't, and what Johnny Rotten could only pretend to possess. Bono, lead singer of the group U2, knows what it is, and admires it in Sinatra. Asked to sum him up after they sang together on the album Duets in 1993 he said: "Rock'n'roll people love Frank Sinatra because Frank Sinatra has got what we want: swagger and attitude. He's big on attitude - serious attitude, bad attitude. Frank's the chairman of the bad. Rock'n'roll plays at being tough, but this guy is ... well, he's the boss of bosses. The man. The big bang of pop. I'm not gonna mess with him. Are you?"

Their collaboration was recorded in studios on opposite sides of the Atlantic. It was one of the bolder ideas on the album, the coming together of a man whose eminence in popular music pre-dated and outlasted Elvis, and an Irishman with earrings who liked to dress up as the devil in a gold lame suit. But there was a link between them, a swagger and a poise, a presence on stage and in person, an ability to dominate proceedings without seeming to.

There are other contemporary performers who have that elusive quality we might call Frankness: Tom Waits, a master at subverting the art of the saloon bar singer; Nick Cave, the Australian gothic balladeer; and kd lang, the lesbian crooner. All three would have appalled Frank but their way with a lyric, a suit and an audience would have been familiar.

There is a catch to all this that our barfly should be aware of: to get away with attitude like Sinatra's, you've got to be a genius. Presenting his elder with a Grammy award for a lifetime of achievement, a nervous Bono described him as "this singer who makes other men poets, boxing clever with every word, talking like America. To sing like that, you gotta have lost a couple of fights."