Whitney Port (Seasons 1-4)
Then: Whitney was Lauren’s lovable, fashion-focused work friend (first at Teen Vogue and then at People’s Revolution). She was asked to model in one episode, and we all cringed when she tripped. Although they tried to integrate Whitney into the casts’ social lives in the later seasons, it was clear she was most interesting at work.
Now: Whitney did her own Hills spin off called The City about her move to NYC to work for Diane von Furstenberg (and later People’s Revolution, again). The show ran for two seasons before ending in 2010.
Whitney has her own clothing line, Whitney Eve, and she’s set to judge Season 7 of Britain & Ireland’s Next Top Model.