SARAH JESSICA PARKER: 2000
Yes, Sex and the City was a fashion phenomenon and made SJP into a style icon. But that doesn't mean Carrie Bradshaw's signature look should be attempted off-screen, even by the star herself. And if her ballet-inspired, feathery tutu ensemble wasn't over-the-top enough, that enormous rosette armband pushed this into Scary Bradshaw territory. Hey, at least the shoes are great!