With apologies to Clint Eastwood, America's original "million-dollar baby" was born in New York City in 1912. Doris Duke won her nickname as the only daughter of the tobacco and energy magnate, James Buchanan Duke; when he died before her 13th birthday, she became one of the richest—and most independent—young women in the world. She was married twice, to James Cromwell and the Dominican playboy Porfirio Rubirosa, and her company was sought by the likes of Errol Flynn, Truman Capote, Elvis Presley, and Jackie O. Although she eventually donated upwards of $400 million to charities, one of the best-loved stories about this avid traveler and collector of Islamic art involves a Middle Eastern businessman and a jet plane. (She wouldn't agree to his price until he sweetened the deal with two camels; Duke named them Princess and Baby and ordered custom-made trailers for their transport.) She was just as lavish when it came to couture: Cristobal Balenciaga, Christian Dior, and Madame Grès were among her favorites. At six feet tall, with wavy blond hair, a pronounced jaw, and piercing blue eyes, she was a designer's dream. An exhibit celebrating her extraordinary collection, "Jet Set to Jeans: the Wardrobe of Doris Duke," is on display at her "Rough Point" Newport mansion through November 5.

—Sarah Cristobal