The Unofficial Preppy Handbook

Wading through the surf in khaki shorts and a button-down with the sleeves rolled up, JFK had a casual breeziness that has had a lasting effect on American fashion designers in the past four decades. The youngest US president was the first major political figure to ditch the suited uniform that so many of his predecessors adopted, introducing the laid-back elegance of navy blazers to the White House. Given his privileged upbringing, this sartorial distinction came naturally to him, and he rocked it with aplomb. “That guy took every nerdy, hokey, ridiculous element of East Coast Ivy League waspy, preppy clothes and somehow made them feel cool,” quips Band of Outsiders’ Scott Sternberg, who borrows and twists many of these elements for his collections. For spring, Sternberg reinterpreted his muse as a California surfer with dip-dyed shirts and a range of pale polo shirts. Michael Bastian, the former men’s fashion director at Bergdorf Goodman, has tapped into this classic American look since launching his eponymous line in 2006. “It’s a perfect uniform for men—you know you will never look inappropriate,” he says. Patrik Ervell was also on the preppy trail for spring, showing pastel jackets, cuffed slacks and neat round-collared shirts for a contemporary take on country club attire. With blue-blood style ever-present on the catwalks, it’s no surprise that the sidewalks of Williamsburg, Brooklyn, and Silver Lake, Los Angeles, teem with hipster-prepsters in chinos, checked shirts and Sperry boat shoes—perhaps listening to Columbia-educated indie poppers Vampire Weekend, who have co-opted this geek chic, on their iPods. Of course, for American sports casual there’s no better master than Ralph Lauren, a former salesman at Kennedy’s frequent outfitter Brooks Brothers who truly defined preppy style in the latter half of the 20th century and continues the tradition today.