Astaire compared dressing well to putting on a show: You have to rehearse it to get it right. Here are 25 men, 10 from the past, 15 from the present, who have gotten it right.

By Alan Flusser

Dressing well is a rare masculine art. No one is born with a predilection for wearing domes with great style. It is not a subject taught in school or even traditionally considered very manly. It involves small acts of daily courage. Tn the heyday of male elegance, the 1920s and ’30s, the best-dressed lists comprised men who were either royalty, film stars, or socialites. Those who were unusually stylish learned it through a tutorial process, from a father or even a valet, or somehow managed to elevate themselves into a social circle where it could be gleaned from those already in the know.

Although it often seems that the most stylishly dressed men come from a life of privilege, more than two-thirds of the living swells on this best-dressed list hail from less rarefied backgrounds. Fashion has become an equalizer, instead of a definer, of social rank.


Fred Astaire


He could wear a suit from Savile Row or a cowboy Shirt from Woolworth’s with equal flair. Rambling along with his hands in his pockets, the pants just short enough to show his socks, and thus his feet, Astaire was sartorial poetry in motion. One item he popularized was the white Brooks Brothers buttondown shirr, which had been considered somewhat sporty. He wore it pinned, with a in-hand or Windsor knot, even with a dark double-breasted suit and a dressy Macclesfield wedding tie. All of Astaire’s clothes were worn for punctuation and motion; on him they looked as if they were moving even when he was standing still. Nobody wore clothes like Fred Asraire.


Tom Wolfe


Wolfe uses clothes both to attract and to repel. “I love to sit and observe people observing me,” he says. A rather formal man, Wolfe eschewed society’s tilt toward casual clothes during me ‘6os. Si nce then he has presented himself as a modern version of a nineteenth-century Virginia gentleman (he was born there) and remains slightly out of step with modern dress. His clothes are extremely well made. White is his navy blue. When assembled in his two-tone hat and shoes, with Regency cane, he strikes us as a sartorial provocateur who promises that, if we watch, something will happen.


Gianni Agnelli


It’s said that ninety-nine out of a hundred Italians know the name of the pope, but a hundred out of a hundred know the name Gianni Agnelli. As heir to the fabulous Fiat fortune, young Agnelli had a long run in the gossip columns before he arrived in the financial pages. Along the way, the “rake of the Riviera” developed some idiosyncratic dressing habits that have been assimilated into mainstream Italian attire. Agnelli is known for sporting his tie outside his sweater as well as for wearing button-down shirts with their collar buttons undone. Even more impressive, however, is that his habit of wearing his watch over his shirt cuff has been adopted by a seeming majority of well-dressed Italians. The Caraceni-tailored Agnelli is Italy’s substitute for royalty.


Ralph Lauren


No one wears blue jeans and a worn T-shirt, white flannels and a tweed jacket, or army fatigues and a pair of paratrooper boots with more style than Ralph Lauren. He uses his own wardrobe as a canvas, a work in progress, for what he is thinking. He has elevated the taste level of an entire generation. Designers from Christian Lacroix to Marc Jacobs wear his styles. Lauren understands great clothes and how to wear them.


Douglas Fairbanks Jr.


One of the paragons of Anglo-American taste, Fairbanks can still be seen sauntering down Fifth Avenue, turning the heads of admiring women. Sporting one of his impeccably tailored thirty-year-old Savile Row suits, punctuated by a crimson boutonniere, Palm Beach tan, and silver hair, Fairbanks looks every inch the famous Hollywood movie star he is. At the age of eighty-three, Fairbanks is a treasured glass of fashion, mirroring those marvelous Laurence Fellows illustrations that appeared in Esquire during the 1930s.


Spike Lee


Lee dresses the way he makes a films: He takes widely divergent ethnic styles, mixes them together, and creates a synthesis that is universal. His approach to fashion includes both hip-hop street influences and classic men’s-wear motifs. The directorial skill with which he combines them is the key. He favors Annani jackets most of the time, accessorized with Malcolm X cap, secondhand shirt with funky tie, and a Kente-cloth scarf. But he can also be seen in a wool poncho, band-collar shirt, and granny glasses. He is one of the few filmmakers working today with a strong, consistent, personal sense of style. No wonder he has successfully started his own clothing line.


T. Reed Vreeland


Although Vreeland never had the bottoms of his shoes polished, a la Beau Brummell, he did have three diiierent-colored fresh carnations waiting for him each evening on his dressing table. He wore his suits and dinner clothes doublebreasted and nonvented. He did not go in for flamboyant clothes, and what he did own, he owned four or five of, such as navy suits and suede shoes. His gold pocket chain had a whistle for taxis and a four-inch Champagne swizzle stick. When his wife, Diana, the high priestess of American fashion, first saw him, she said that he was the most beautiful man she had ever seen.


–Excerpt of article taken from Esquire Gentleman Spring 1993