The Lessons of J.F.K.

Every president has left a mark on American style, from Harry Truman's penchant for Hawaiian-style sport shirts to Dwight Eisenhower's cropped military jackets and Ronald Reagan's custom-made Hollywood glamour. But it was the simple sartorial gestures of John F. Kennedy that really shaped 20th century American style. The images are iconic now—a rolled-up sleeve, an untucked shirt, a shaggy head of hair—like something out of a J.Crew catalog or a Ralph Lauren advertisement. But in 1961, Kennedy's confident, carefree style was a radical departure from the copycat boxy gray suits and felt hats that had defined men's fashion for previous generations.

Among other things, Kennedy banished hats for men, even disposing of the top hat for his inauguration speech. He also traded in the three-button suit for a baggier two-button style (to accommodate his back brace) and reintroduced the casual blue blazer both in the White House and on trips to Hyannis Port. Less well known is that for all the unself-conscious air that his wardrobe conveyed, J.F.K. went to the trouble of having much of it made by a tailor in London, a sartorial standard he had come to appreciate as the son of U.S. Ambassador Joe Kennedy and one that his wife Jackie and sister-in-law Lee Radziwill thought should be the natural beginning point for a man of style.

But Kennedy's cool factor—the sunglasses and convertible cars—was all his own, and it's what made his look memorable. "The ease of his style made it really look like he didn't think that much about it," says menswear designer Thom Browne, who has been indirectly influenced by the Kennedy look in his work for his own label and for Brooks Brothers' Black Fleece collection. "He had a pure sense of American style that was so masculine and appealing. I think people are starting to appreciate that style again."

Some designers have even gone so far as to collect Kennedy possessions. Diego Della Valle, president and ceo of Tod's, the Italian shoe and handbag manufacturer, purchased Kennedy's 1930 Marlin boat in 1998. But it is from Kennedy's clothing cues that they draw inspiration, including his preference for chinos, polo shirts, two-button suits and Ray-Ban sunglasses. "His unstudied sense of style is a constant touchstone when I design my men's collections each season," says Michael Kors. "He ushered in a whole new era of style—a convergence of Old World elegance and casual modernity."