1999: Gwyneth Paltrow

There’s no denying that Gwyneth Paltrow’s pale pink Ralph Lauren gown that she wore to the 1999 Academy Awards ranks among the finest of all time. It’s one of her most talked-about looks, and given that it all dates back to 1999, this is no minor achievement.

Paltrow earned an Academy Award nomination for her performance as Viola De Lesseps in Shakespeare in Love. The actress arrived at the Dorothy Chandler Pavilion dressed in a bubblegum pink taffeta ball gown. The cut has lasted the test of time, symbolizing all that was characteristic of the era. Gwyneth didn’t have a stylist at the time and instead went to Lauren a few days before the event to pick out a dress. It came with a corset-like top replaced with the more wearable one we all know and love. Paltrow pulled her blonde locks back into a neat bun on the right side.  She paired it with a pink shawl and a $160,000 worth of Harry Winston diamond choker, bracelet, and earrings. Well, given her fame and investments, this wouldn’t come as no surprise.