Age: 28 (born in 1980 with the publication of The Official Preppy Handbook)

Call him Chad. Or Chip. Or Holden. Call him whatever you like, old sport, as long as you'll join him for a Bloody Mary by the tennis court while he gabs about the true meaning of power. He is the great American preppy, and while his plaid, country-clubbish influence has ebbed and flowed over the decades, he's never really gone away. In fact, the buttoned-down, wing-tipped, Bermuda-shorted, madras-clad prepster is like jazz or cheeseburgers—a classic American export—and it's during times like these, when everything seems to be in flux, that we always come back to him. Consider the ascendance of Gossip Girl's Upper East Side snot, Chuck Bass, and the steady resurgence of the populist-prep label J. Crew. Consider fashion designers like Michael Bastian and Band of Outsiders' Scott Sternberg, who have turned Ivy League tropes upside down, and Kanye West's evolution into the fresh prince of Nantucket. So prevalent is the preppy virus that it now infects even rock and roll, which has given us a bumper crop of campus bands (Vampire Weekend, Chester French, Ra Ra Riot, MGMT) that look natural in tennis sweaters, rep ties, and Wayfarers. Hell, the stock market has crashed and Robert Chambers is heading back to prison—gentlemen, let's clink our brandy snifters to Sherman McCoy. It's 1987 all over again!

29. LIL WAYNE, CROSSOVER KID >>