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13. JFK, Jr. and Carolyn Bessette-Kennedy

It goes without saying that preppy runs in the Kennedy family, and JFK, Jr. is no exception. In 1996, he married Carolyn Bessette, at the time a publicist for Calvin Klein, and the two garnered instant media attention for their style and, of course, the Kennedy name. Here Carolyn and John, Jr. are photographed at the Municipal Art Society's presentation of the Jackie Onassis Medal to Stephen Swid in New York, April 1998.