Hillary Swank won her first Oscar as Best Leading Actress in 2000 for the film ‘Boys Don’t Cry’. She looked amazing. She wore a strapless bronze silk gown from Randolph Duke. She accessorized it with a $250,000 diamond necklace from Asprey & Garrard. The necklace was originally created in 1890 for one of Queen Victoria’s daughters. It can be turned into a tiara.