2000: Hilary Swank

If you’re going to attend the Academy Awards knowing that you have a shot at going home with an Oscar for Best Actress, you better dressed up as a winner. Fortunately, Hilary Swank got the memo and walked down the carpet dressed in this bronze-colored ball gown designed by Randolph Duke.

As you probably expected, the actress did take home an Oscar that night, and her first one, for that matter. Swank looked absolutely gorgeous when she was photographed with her trophy backstage at the Oscars press room. The dress might have even given the actress some degree of good luck as her career skyrocketed after taking home that first Oscar. After that, she’s also had a couple more iconic moments, including her bare-back Guy Laroche dress that she wore to the 2005 Academy Awards. This lady is definitely a force to be reckoned with, both in film and fashion.