2005: Hilary Swank

Hilary Swank in 2005 saw her greatest achievement yet when she won an Oscar for her leading role in Million Dollar Baby, directed by Clint Eastwood. While her achievement is certainly front and center, her dress during the occasion is perhaps one of the most well-known and iconic dresses in the history of Oscars. Swank wore a navy blue, a back-baring gown made by Guy Larouche. The gown gave the star a femme fatale look, especially since she had a fit physique, which can be given credit to her training for Million Dollar Baby.

Immediately, the dress was praised by many. It became one of the best dresses, not only during that Oscars ceremony but also in the history of the Oscars. In addition, many had said that the gown is one of the best red carpet gowns of all time. Swank certainly wowed plenty of people back in 2005.