Lupita Nyong’o

Most celebrities don’t get their Oscar red carpet fashion moment right the first time, but that wasn’t the case for then-budding actress Lupita Nyong’o. Lupita stunned everyone when she wore this baby blue gown from Prada to the 2014 Oscars where she won Best Supporting Actress for her role in “12 Years a Slave”.

The flowy dress, which features a low neckline, was an elegant piece fit for an Oscar awardee. In the movie, Lupita may have struggled with bankruptcy as slaves, but that night at the Oscars, she looked like a princess from a noble family in a fairytale.