Gwyneth Paltrow (1999)
It wasn't the best fitted gown in terms of its bodice, but the pale pink Ralph Lauren was a perfect fit for the moment when Paltrow tearily accepted her Best Actress statue (for Shakespeare in Love) and ascended to the role of Hollywood's crown princess.
Image Credit: Jeffrey Mayer/WireImage
The red carpet at the Academy Awards is a tricky place -- when the fashion's good it's very good, but when it's bad...oh my. Here are our picks of 30 actresses' unforgettable fashion choices -- for better and worse