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4. Whitney Port

Whitney Port first made her appearance on The Hills as Conrad's fellow intern at Teen Vogue. The two continued along their shared career path until Port blazed her own trail to New York City to work for Diane von Furstenberg, which resulted in her own spin-off series The City. She currently has her own clothing line, Whitney Eve, and a style book under her belt. 

She is currently engaged to one of the show's producers, Tim Rosenman.