6 Times Jennifer Aniston Dressed For Revenge

When it comes to revenge dresses, one instantly thinks of Princess Diana and her iconic off-the-shoulder black minidress, which she rocked after her ex, then-Prince Charles, publicly admitted to having an affair during their marriage. But what exactly is revenge fashion? Since Princess Di's unforgettable fashion moment, the term has become synonymous with a spectacular look that one decides to go for after a breakup. And the truth is that every celebrity has at least one incredible revenge-dress moment.

Today, our topic of discussion is Hollywood star Jennifer Aniston, who has dated (and been married to) quite a few Hollywood heartthrobs. While Jen is known for her laid-back and simple approach to fashion, her revenge-dress moments still showcase her strength, resilience, and beauty, which is kind of the entire point of an incredible post-breakup look. From Brad Pitt to John Mayer, these men undeniably didn't have it easy when they saw Aniston looking her absolute best.

In early 2005, news of Jennifer Aniston and Brad Pitt's separation broke, after months of speculation that Pitt was more than just co-stars with "Mr. & Mrs. Smith" actor Angelina Jolie. And while Angelina Jolie had a stunning style transformation, our sole focus is on Jennifer Aniston's post-separation fashion. In October 2005, Aniston showed up to the premiere of her film "Derailed," and all eyes were instantly on her. The champagne halter dress was simple and sophisticated, and the glitter material made it extra glamorous. 

In December 2006, Jennifer Aniston and Vince Vaughn confirmed their separation, and while it seemed amicable, Aniston still couldn't miss a chance for a fun revenge-dress moment. For the premiere of the drama series "Dirt" that month, in which she starred alongside her "Friends" co-star Courteney Cox, Aniston decided to go with a fail-proof classic: a little black dress. Having one in your closet is crucial, and luckily, finding your perfect LBD type no matter what your style is isn't that difficult.

Before there was Brad and Jennifer, the "Friends" star was actually part of another iconic '90s couple. From 1996 until early 1998, Aniston dated actor Tate Donovan. Once they split, she gave us a fun fashion moment at a VH-1 Divas event in New York City. The actor showed up in a maxi skirt and a matching long-sleeved top in slightly see-through material — especially noticeable in flash photography. Whether the look was on purpose or not is something we'll probably never know, but regardless, it resulted in a perfect revenge-dress moment.

After Jennifer Aniston's whirlwind romance with musician John Mayer, the two went their separate ways (before reuniting later that year) in August 2008. Soon after, Aniston attended the Toronto International Film Festival for the premiere of her rom-com "Management." The "Horrible Bosses" star showed up in a little black dress with a halter top that was definitely one of her more daring post-breakup choices.

In early 2018, Jennifer Aniston and actor Justin Theroux revealed that they were getting divorced after almost three years of marriage. A few months later, Aniston attended the American Film Institute's Life Achievement Award Gala in a stunning black gown. While her gown was beautiful and sophisticated, what made the moment even better was that Aniston attended the event with her close friend Courteney Cox. Both ladies wore black gowns, proving that a revenge-dress moment is that much more powerful alongside friends.

In early 2010, Jennifer Aniston and actor Gerard Butler were rumored to have had a brief romance on the set of their rom-com "Bounty Hunter." Neither of the two ever confirmed a relationship, but that won't stop us from looking at Jen's fashion after their rumored breakup. As the actor was promoting her rom-com "The Switch" in the summer of 2010, a specific revenge look instantly came to mind. Aniston showed up to the LA premiere of the project in a skin-tight nude tube top and black miniskirt. The look was effortless and fun, showcasing the star's stunning physique.