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Ivanka Trump & Jared Kushner
She may not be an actual princess, but Ivanka Trump certainly behaves likes one. While other socialites like Paris Hilton and Kim Kardashian chose to skip college in favor of starring in sex tapes, Ivanka Trump went to business school, making her about as smart as a former model/heiress can be in the U.S. After designing her own jewelry collection (and famously rubbing elbows with Prince Harry at a polo match,) Ivanka married fellow Ivy Leaguer Jared Kushner in 2009 and sought out Vera Wang to design a wedding gown that was inspired by the dress that Grace Kelly wore when she married Prince Rainier. The couple is expecting their first child this summer, reportedly a baby girl.