I first met Tommy Hilfiger around 1990, when he was already well known in the fashion industry. In the late 1960s he’d been a teenager in upstate New York, but he wanted access to fashionable clothing that he couldn’t find in local stores. So he and some friends would drive to New York City, buy dozens of pairs of bell bottoms and other hippie clothing, drive back upstate, and sell the clothes from the trunk of his Volkswagen. Before he was 20 Tommy and a partner had opened a basement shop called People’s Place, which grew into a small chain of stores. By the mid-1980s Tommy had moved to New York City and found a backer to launch his own brand: classic East Coast clothing with a casual, carefree twist inspired by time he’d spent in California. In 1985 his ad agency put up a billboard in Times Square that compared Tommy Hilfiger to Calvin Klein, Ralph Lauren, and Perry Ellis. It was a bold statement, but it put him on the map—and he had the creative vision to deliver on it.

A version of this article appeared in the July–August 2015 issue (pp.33–36) of Harvard Business Review.