Angelina Jolie Outfits That Just Didn't Work

When it comes to talent and looks, Angelina Jolie has both in amounts that feel almost unfair. She's mastered old Hollywood looks in a way that other celebrities just haven't, and onlookers know she always brings her A-game to red carpets and other events. Some of her most stunning moments in the spotlight have even made those around her seem to disappear. But, somewhat shockingly, this wasn't always the case.

If you jump back to Jolie's early days in Hollywood, her approach to fashion was ... interesting, to say the least. Granted, Jolie has always had a rebellious streak, especially by Hollywood standards. While she was in her 20s, though, her approach to fashion wasn't just about proving she was an outsider — many times, it seemed as if she honestly didn't care what others might have had to say about what she wore. While that can sometimes be a great thing, Jolie's anti-trend philosophy also led to outfits that just didn't work. "There are more books than clothes in my closet," Jolie told Vogue in 2023. "I'm not someone who likes clothes to consume her life. And I don't love the idea of being 'influenced.'" 

So the next time you're flipping through old photos of yourself, cringing at what you were wearing 10 or even five years ago, know that you're not alone. If Angelina Jolie can have a whole slew of outfits that missed the mark, then so can the rest of us.

In 2000, Angelina Jolie won the Academy Award for Best Supporting Actress for her performance in 1999's "Girl, Interrupted." For the event, Jolie wore a full-length, long-sleeved black gown that made it seem like she was off to summon the dead after the awards show was over. While the goth look is something that never really goes out of style, it's a bit intense for the Oscars — especially if you're nominated and might win.

That was also the night that Jolie cuddled and kissed her brother in a way that left onlookers scratching their head. "My parents really loved that moment, and that's what will always matter," Jolie told Entertainment Weekly in an interview a few months later about her tribute to her brother and the displays of affection.

As far as fashion goes, 2000 was a really rough year for Angelina Jolie. Although her career was certainly taking off thanks to her role as Lisa in "Girl, Interrupted," what she wore was far less successful. For the 57th Annual Golden Globe Awards, Jolie wore a casual white gown and what appears to be a matching, oversized jacket, all of which just washed her out. It's hard to tell if a pop of red on her lips would have helped or hurt the situation.

While one absolutely has to admire the fact that Angelina Jolie showed up to the premiere of her film "Lara Croft: Tomb Raider" in low-rise leather pants that revealed a few of her many tattoos, it's still a look that just didn't work. It may have fit the mood and energy of the movie, but you'd think she would dress up for a premiere of a movie she's starring in. It's also worth noting that this was Jolie's Billy Bob Thornton era — who attended the premiere with her — which may have influenced her outfit choice.

Unless you're a politician making a statement, the monochromatic white look is a hard ensemble to pull off. What makes it even harder is trying to figure out what shoes to wear that make sense aesthetically — and a white, closed-toe shoe definitely isn't it. However, that's exactly the look Angelina Jolie tried to rock back in 2001 while attending the Vanity Fair post-Oscar party with her dad, Jon Voight. It's also a look that really failed her.

In 2007, Angelina Jolie attended a photocall for her film, "A Mighty Heart," at the 60^th Annual Cannes Film Festival in France. Although it's difficult to know what was going through Jolie's head at the time, she may have confused the photocall with casual Friday at the office based on her outfit choice. Even her black peep-toe pumps were a questionable choice for a movie star of her caliber. The only thing about this look that kind of works is the fact that Jolie's makeup is barely there, proving that she's just as gorgeous without makeup as she is with it.