In the canon of Americana, Tommy Hilfiger is right up there with apple pie and the 4th of July. "When I first started as a designer, I wanted to make the preppy look feel modern and fun with my own twist," he says. "Using new fabrics, fits, and bright colors, I wanted to break all the rules and write a new chapter of classic American cool." Make that chapters. This season’s installment is a "mix of collegiate prep and an irreverent take on British sartorial tradition," he says. Inherent in the houndstooth knits and Prince of Wales checked shearlings: an Old World meets Ivy League sensibility. As for what happens next, the rest is still unwritten."Annie Leibovitz, Conde Nast Archive/Corbis"