Angelina Jolie's Best Old Hollywood Looks That Prove She's The Ultimate Movie Star

Since she became a household name, Angelina Jolie has proven time and again that she's not like the rest of Hollywood. From the roles she chooses to her array of meaningful tattoos and her international humanitarian efforts, Jolie is absolutely one-of-a-kind — something she also reveals in the clothes she chooses to wear.

"I've never been to a fashion show or Met Ball my entire life," Jolie told Harper's Bazaar in 2023. "I love individuality and I love freedom." In September 2023 when talking about Atelier Jolie, Jolie shared her thoughts on how what one wears is truly a form of self-expression. "Because we live in our clothes, it is so much a part of who we are, and something that's important to explore, especially for young people," Jolie told Vogue. "I've always wanted to take my family to a place where I can say: Does your clothing really represent you? Absolutely you? And do you love it?"

It's this mentality that Jolie brings to her red-carpet choices. She's not dressing for us, she's dressing for herself, and the old Hollywood looks she continues to wear prove she has her unique movie star style down to a science.

In 1999, Angelina Jolie won the Best Actress Golden Globe for her performance as supermodel Gia Carangi in the HBO film, "Gia." Although she was still very early in her career, she had nailed what it meant to rock an old Hollywood look with this sparkly, fitted, floor-length gown. While we didn't know it then, that dress was just the beginning of gown choices that would make Jolie look like she'd been plucked out of the '40s or '50s.

In 2001, Angelina Jolie showed up to the Golden Globe Awards in Beverly Hills rocking another full-length gown. This time around, it was a rose gold number from Versace. This appearance was during her Billy Bob Thornton era, as she has his name tattooed on her arm; this was just the beginning of all the dozens of tattoos to come.

If you thought only Marilyn Monroe could pull off a white satin dress with a deep V-neck, you were wrong. In 2004, Angelina Jolie attended the 76^th Annual Academy Awards in a Marc Bower gown that was very reminiscent of the one Monroe wore in the "Seven Year Itch" during the scene where the subway famously blows up the skirt of her dress. Jolie's look included a matching wrap and one less tattoo, having divorced Billy Bob Thornton in 2003.

When Angelina Jolie showed up at the 68^th Annual Golden Globe Awards in a gorgeous emerald green gown by Atelier Versace, proving that the old Hollywood look doesn't always have to be a neutral color. With her long dark hair and striking eyes, the color combination was stunning. To make sure the emerald gown was the focal point, Jolie kept her makeup subtle, staying away from the red lip she often dons. 

Even if you didn't watch the 84^th Annual Academy Awards, you've probably seen the photos of Angelina Jolie posing with her leg prominently out. Once again in Atelier Versace, Jolie's leg didn't just become the star of the show, but the subject of many memes that followed. "I had a more complicated dress and I wore the more comfortable dress, which was that one, and I think I was just so comfortable that...," Jolie told Extra in 2019. "I think when you feel comfortable, when you feel yourself — which is very much the theme of [Maleficent: Mistress of Evil], and we know this in life — you embrace it. And sometimes, maybe it appears to be a thing, I don't know." 

Just a year after opting for a preventative double mastectomy upon learning she had an 87% chance of developing breast cancer due to the BRCA1 gene, Angelina Jolie found herself behind the camera, directing "Unbroken." When she attended the premiere of the film at the Odeon in London, she wore an off-white dress by Ralph & Russo and a very demure and sweet matching cape. Definitely something that Audrey Hepburn would have donned during her career.

In August 2024, Angelina Jolie and her family walked the red carpet at the 81^st Venice International Film Festival for her role in "Maria," a film about legendary soprano Maria Callas. Jolie hadn't been to the festival in almost 20 years and made up for lost time in a gorgeous custom Tamara Ralph gown, a faux fur stole, and bright red lips. The whole look wasn't just old Hollywood, but an absolute nod to Callas who would have worn the same thing. In fact, her brooch reportedly belonged to Callas back in the day, as did the Cartier panther brooch that Jolie wore during her time in Venice.