All the Times Jennifer Aniston Wowed at the Oscars — Including with Brad Pitt!

Aniston’s first Oscars appearance came as she was side-by-side with then-boyfriend and fellow actor Brad Pitt at the 72nd Academy Awards in 2000. The two stepped out together and instantly became an iconic Hollywood couple. That summer, the two wed in a lavish Malibu wedding. The couple separated in 2005 after five years of marriage.

Less than a year after finalizing her divorce with Pitt, the actress walked the red carpet solo at the 78th Academy Awards in 2006. The Friends star looked radiant in a black, scoop neck Rochas gown as she prepared to present the award for Best Costume Design.

Wowing onlookers with a silver Valentino gown, Aniston was accompanied by then-boyfriend, musician John Mayer. The two attended the 81st Academy Awards in 2009. The couple began dating in April of 2008. They split months later.

The actress returned to the 85th Academy Awards in 2013 to present the awards for Best Costume Design and Best Visual Effects. This time, she was joined by her fiancée, actor and screenwriter Justin Theroux. The two began their relationship in 2011, and were engaged in 2012.

Aniston and Theroux’s engagement continued on to their next Oscars appearance, the 87th Academy Awards in 2015, where she presented the award for Best Documentary Feature. Wearing a Versace gown, the actress was all smiles with Theroux. Several months later, the two married at their California residence.

In her first Oscar appearance as a married woman, Aniston attended alongside Theroux as she presented the “In Memoriam” tribute segment. As an international style icon, much of the attention was on Aniston herself, specifically her low-cut black gown and her 20-carat Golconda diamond ring, reportedly worth $1.2 million. Aniston and Theroux announced their separation in February 2018.