Not only did Halle become the first African American woman to win an Oscar, but her super-sexy, sheer Elie Saab gown will go down in history. Needless to say, 2002 was her year.
Despite our modern-day tastes, Gwyneth's pink Ralph Lauren dress from the 1999 Academy Awards is often cited as one of the best dresses in red carpet history. Gwyn is also credited for making the color pink cool again. Oh yeah, this is the year she also won an Oscar for her turn in Shakespeare in Love. No big deal.
If you didn't know who the co-creators of South Park were before, you did in 2000. The comedic duo brought their sense of humor to the red carpet via two iconic looks resembling Jennifer Lopez's Versace Grammys dress and Gwyneth Paltrow's aforementioned Ralph Lauren gown.
Let's be real: Not everyone was familiar with the Icelandic singer-songwriter before the 2001 Academy Awards. Today, Björk in her swan dress are forever emblazoned in our minds.
Angelina has been an A-lister of years, but her leg, on the other...hand, went viral seconds after it hit the red carpet. As fierce as it may be, we couldn't help but smile with every new meme.
OK, it was Lupita's red Ralph Lauren cape number from the 2014 Golden Globes that really cemented her place as a style star, but when she showed up at the 2014 Oscars in a blue, Cinderella-esque Prada gown and a beaming smile, we knew she'd had stolen our fashion-loving hearts for good.
Not many actors make a splash on their first trip to the Oscars, but in 2011, everybody was wondering who was the girl in the strikingly simple Calvin Klein dress. Her name was Jennifer, and she won our hearts over and over with her real personality and stumbles in couture gowns.
We know you can't technically have more than one breakout moment, but Gwyn deserves two mentions here. Before Lupita's cape dress or Solange Knowles' Humberto Leon for Kenzo wedding dress, Gwyneth rocked the cape in 2012 Tom Ford. Scratch that, this is the cape's breakout moment.