Cigar Aficionado

"Yankee Doodle went to town riding on a pony, stuck a feather in his cap and called it macaroni."

Hidden in that lyric, known to every child, is the key to understanding American style.

Some history will help. A British army surgeon penned the ditty while serving in the French and Indian War, meaning to poke fun at the rough-hewn colonialists he encountered. Yankee Doodle was a rube riding his farm animal to town from the country. Macaroni was the slang for the young London swells who had made the Grand Tour of Europe and returned from Italy with a taste for the finest menswear and presumably pasta as well. The joke is that our hero, this country bumpkin, thought a feather in his cap was the height of fashion. But far from being insulted, Americans made the tune their marching song when they fought the War of Independence.

A Brit had inadvertently made the Americans' fashion statement for them: a great look involves cheek, insouciance and minimalism, all rolled into one. The restive colonials were what they were, and they didn't need flowing Italian silks or elaborate uniforms to be dandies -- or, for that matter, to win the war. Sometimes all it took was a feather in the cap. Even if we rebels occasionally still kowtow to the fashion monarchs of Europe, that easy approach to fashion is the hallmark of all that's best in American style.

"The great lie is that Americans don't understand fashion," says Martin Nicholls, from his perspective as a New Zealand-born Brit and Savile Row-trained tailor most recently employed in the New York outpost of Dormeuil, the Paris cloth concern. "You may have an inferiority complex, but I love America because it's full of contradictions and ironies. You needn't dress to define who you are. In Europe, dress was a form of social segmentation. They used uniforms to stop social climbers. Americans never have."

While what is now the business suit may have been invented in England some 200 years ago as a takeoff on sporting outfits, it was the Americans who made it universal, made it stick and made it easy. Had it been left to Savile Row and its virtuoso custom tailors, the look would never have been affordable but for a privileged few. Around the 1820s, America developed ready-to-wear suits that the majority could afford as well as fit into consistently. Then Americans wore them to work, and suddenly the world had a uniform in which to do business -- a good start for a planet that was rapidly becoming industrialized.

America's contribution to the suit in of architecture was, true to form, the sack suit. While the English model of the suit was all about form and strictures -- tight waists, sharp shoulder -- which, truth be told, was ultimately unflattering for many physiques, suit makers on these shores made the uniform easy. The classic American takes -- Brooks Brothers, Hickey Freeman, Hart Schaffner & Marx, Ralph Lauren, Tommy Hilfiger, and so on -- have been close to shapeless with soft shoulders, but somehow imbued with an elegance that transcended strict lines. The fabrics, too, have always said comfort. Americans showed up at the office in linens, seersuckers or whatever felt right, and today super fabrics and all-season cloth are making it easy for travelers to do business anywhere.

But it was when America was at real work that it made perhaps its greatest fashion statement: blue jeans. Developed to stand up to the rugged toil of 49ers and cowboys, no garment bespeaks casual style more eloquently than denims. Even the florid dandy Oscar Wilde recognized that when he toured America and pronounced the Rocky Mountain miners the only well-dressed men in the country. Soon dungarees crept into every walk of life and reached across the globe as the international symbol for the laid-back look of the United States. They reached their peak in the 1970s when designers like Calvin Klein made them form-fitting for the disco age, but blue jeans as shapeless tros will always be in style -- even when paired with black tie and cummerbund. Logical extensions of dungarees as casual pants are Levi's 501s and khaki tros, even when realized in a hyper luxurious way, such as done by Bills Khakis.

Americans even managed to make formal wear easier. Before 1886, the black tailcoat with white tie was the uniform for formal occasions. But that year, Griswold Lorillard, a tobacco fortune scion, arrived at the Autumn Ball in Tuxedo Park, New York, an enclave of the super rich, wearing a coat with no tails and eliciting both shock and delight. Some say the Prince of Wales had introduced the style a year before, but clearly it was Grissy, the prankish American, who was able to carry it off, for the black dinner jacket is now called a tuxedo. "The tuxedo was legitimized in Europe," says Nicholls, "but it was born in America."

The twentieth century brought jazz and cinema, America's other original art forms. With them came dress that was at once stylish and fun. Bebop musicians, with their zoot suits and berets, played their wardrobes as irreverently as their flatted fifths. The rockers who displaced them came in all sorts of packages, from the outrageous Elvis looks to the unkempt-beatnik-in-sweatshirt approach, but one thing was clear: the days of performers and audience uncomfortably cinched into monkey suits were gone forever.

While the movies have given us their share of elaborate costumes, the styles that actually came out of Hollywood were always easy. The movie stars were seen at play in elegant but simple casual wear. Clothes for lounging were the invention of a class of people who wanted to seem at leisure even as they worked hard. And on the silver screen, those who dressed stiff were always consciously portraying just that. Or they were gangsters, trying to seem legitimate in their illegitimacy. The guys we rooted for took it cool and light. Fred Astaire may have danced through countless movies in white tie and tails, but his lasting impression on fashion was made with the sports clothes he wore so effortlessly. Then again, Astaire could make tails seem effortless.

Then America invented the teenager. It started with Andy Hardy and his puckishly flipped-up caps, made its way through the malt shops, prep schools and discotheques, until it was universally recognized that here was an age demographic free to develop its own fashion. The awkward years were no longer awkward as teenagers eschewed both children's clothes and adult garb for their very own look. And the look was typically flippant. Who else could go through life with shirttails out and shoelaces dragging? Even the supposedly straitlaced preppy look was a goof, all layers and draped on sweaters, duck shoes with no socks paired with blazers. When the quintessential teenage generation -- the baby boomers -- grew up wanting to be nonconformists just like all the other guys, they insisted on retaining their easy fashion approach, and we got the business casual look.

And so the distinction blurs between what is work and what is play. "Leisure time in America is big, despite the fact that Europe has more holiday time," observes Nicholls. Americans attack leisure time when they can get it in a whole assortment of outfits meant to telegraph comfort and fun. Hence we have technical fabrics, like Gortex, used as a fashion statement. When we're on actual vacation, out come the clothes that say, "the hell with it": wild T-shirts, shorts and Hawaiian prints, as though we've all just arrived at Disneyland. The clever marketers behind the Tommy Bahama line of tropics wear have touted their company philosophy that "life is one long weekend" by creating the fictional and eponymous Tommy character, who bops through life from one island resort to the next in luxury duds made for playtime.

Neither do Americans care much if their dress is appropriate to what they are doing. Hardy Amies, sometime couturier to the queen of England, once sniffed that he would never make a hacking jacket unless it were actually intended for riding. The American approach is the polar opposite, according to Nicholls. "You wear rugby shirts, but never for rugby." Sometimes the result of such desultory behavior is really quite odd. The button-down shirt, made emblematic of staid business attire by Brooks Brothers, was originally a Brit garment for polo playing (the shirt collar wouldn't flap in your face).

Yet despite the contradictions and anomalies, Nicholls points out, "of all the influential people in the fashion world, almost half the top guys are American. And it will stay that way as long as you don't take it too seriously."