Sophia Michaels
Angelina Jolie is known for her bold fashion choices and has often sparked controversy with her daring outfits. Over the years, she’s worn numerous looks that not only captured attention but also reinforced her iconic status as a femme fatale, landing her spots on both best and worst dressed lists.
However, her fashion isn’t the only thing that’s kept her in the headlines. Jolie’s personal life has often been the subject of media scrutiny and scandal. She has been involved in numerous controversies, including one of Hollywood’s most infamous love affairs. Yet, she seems to remain unfazed by the attention.
Nowadays, Jolie has shifted focus towards her children, her career, and various humanitarian efforts since her high-profile breakup with Brad Pitt. Even though the wild days are behind her, her iconic red carpet moments continue to evoke memories, including several audacious outfits that are still talked about today.
Angelina’s Gothic Girl, Interrupted Marc Bouwer Gown
At the 2000 Academy Awards, Angelina Jolie turned heads with a daring, gothic-inspired outfit that broke conventional red carpet norms. Dressed in a striking Marc Bouwer gown with long sleeves and sleek black hair, she embodied a Morticia Addams vibe that set her apart from her peers, who opted for more traditional looks.
That evening, she won the Best Supporting Actress Oscar for her role in “Girl, Interrupted.” However, much of the media buzz centered not on her achievement but on her unusual exchanges with her brother, James Haven. “I’m in shock, and I’m so in love with my brother right now,” she famously said before they made headlines with their public display of affection.
Both Jolie and Haven brushed off the controversies surrounding their sibling bond. “My parents really loved that moment, and that’s what will always matter,” Jolie later commented. Haven clarified that the kiss was innocent and a simple congratulation for her win.
Angelina’s Tomb Raider Leather Look
In June 2001, at the premiere of “Lara Croft: Tomb Raider,” Angelina Jolie surprised everyone by opting for a daring outfit of tight black leather pants paired with a crop tank top. This ensemble, which showcased her tattoos, was a significant departure from typical red carpet attire.
Jolie has always been fearless in challenging fashion norms. Her wedding to Jonny Lee Miller in 1996 illustrated this perfectly—she chose to wear black leather pants and a white shirt adorned with his name written in her blood. She later commented that special occasions needed unique expressions, but their whirlwind marriage ended before long, leading her to reflect on the swift impact of losing her identity in the role of a wife.
Angelina’s Mr. & Mrs. Smith Vampy Versace
At the premiere of “Mr. & Mrs. Smith” in June 2005, Angelina Jolie made a bold statement in a dramatic Versace dress. The gown, adorned with leather and designed to reveal ample cleavage, featured a high slit that added to its daring nature. Interestingly, Jolie and her co-star Brad Pitt only posed for a few group photos together on the red carpet, sparking curiosity due to their on-screen chemistry. This was particularly attention-grabbing as Pitt had recently separated from Jennifer Aniston amid rumors of an affair with Jolie, creating a buzz around their relationship.
Even after some speculation and the need for discretion, the couple later downplayed their romance during filming, maintaining that nothing inappropriate occurred until after the project was completed. However, Jolie eventually confirmed that their connection developed much earlier, sharing her experience of watching the film with their children. “Not a lot of people get to see a movie where their parents fell in love,” she stated in a 2008 interview with The New York Times.
