Though she had already been acting in made-for-television movies and shorts for nearly a decade, Angelina Jolie shot into the public eye in 1999 thanks to her performance in Girl, Interrupted (and also, in part because of her Golden Globes appearance that same year in a clingy sequined Randolph Duke gown). The look marked the actor as one to watch on the red carpet, and more than two decades later, it’s a status she maintains. Though these days, Jolie’s red carpet appearances have been far fewer, every once in a while she treats us and steps out in another classic Jolie look. Over the years, the actress has perfected her style, sticked with sleek silhouettes, neutral colors, and the motto, “When in doubt, call Donatella.” Versace has been her go-to for decades, and it’s easy to see why—their atelier team just knows how to show off Jolie, whether it’s by draping her in velvet or their signature metal mesh.
It’s been a little while since we’ve gotten a new Jolie red carpet moment, but luckily, she has some projects in the works that will mark her return to the press circuit very soon. In the meantime, let’s take a look back on 25 years of Jolie’s looks, from 1998 to now.
2021: Eternals UK Premiere
Jolie provided a unique, voluminous take on suiting in custom Valentino haute couture.
2021: Rome Film Festival
The actress returned to one of her favorite designers and wore Atelier Versace for the premiere of Eternals at the Rome Film Festival.
2021: Eternals Los Angeles Premiere
Jolie’s Eternals press tour was filled with great looks, including this draped Balmain resort 2022 dress.
2019: Maleficent: Mistress Of Evil London Premiere
Perhaps the magic of Disney got to her, because the custom Ralph & Russo couture gown Jolie wore to the Maleficent: Mistress Of Evil was a bit of a departure for the actress.
2019: Maleficent: Mistress of Evil Los Angeles Premiere
Jolie has proven she loves Versace’s metal mesh, so she wore a dress made out of the fabric yet again to the Maleficent LA premiere, setting it apart from the others with a scorpion broach placed on her hip.
2019: Dumbo Premiere
Looking almost like a bride, Jolie stepped out in a slightly more demure look—a white Atelier Versace dress—for the Dumbo premiere.
2018: Critics’ Choice Awards
While it is rare to see Jolie in white, she also embraced the color at the 2018 Critics’ Choice Awards, attending the event in a strapless, draped Ralph & Russo dress, decorated with a bust of feathers.
2018: BAFTA Awards
Jolie also tapped the Ralph & Russo team to dress her in a one-shoulder velvet gown for the BAFTAs.
2018: Golden Globe Awards
The actress returned to her favorite color and designer for the Globes in 2018, wearing a black dress from Atelier Versace featuring a sheer top layer and feather details.
2017: First They Killed My Father Premiere
It’s rare to see Jolie in a classic ballgown silhouette, but the color and simplicity of this Dior fall 2017 couture dress places it squarely in the canon of Jolie’s personal style.
2015: Critics’ Choice Movie Awards
This silver silk Atelier Versace gown looks like it was poured right onto Jolie before she hit the red carpet.
2014: Unbroken Premiere
Jolie almost never wears prints, so it was quite the surprise to see her in this Gucci Premiere black and white lace dress at the Unbroken premiere.
2014: Maleficent Premiere
While this Atelier Versace dress may look to be made of leather, it was actually constructed out of rubberized silk.
2014: Academy Awards
Jolie embraced a bit more sparkle and wore a beaded Elie Saab fall 2013 couture gown to the 2014 Oscars.
2014: BAFTA Awards
Every actress has a Saint Laurent tux phase, and Jolie’s hit around 2014 when she wore this cool, relaxed take on menswear to the BAFTAs.
2012: Academy Awards
Thank to that leg, this black, velvet Atelier Versace dress may be Jolie’s most famous red carpet look of all time.
2012: Screen Actors Guild Awards
While this black dress with a draped neckline is Jenny Packham fall 2011, the metallic, liquid-like fabric almost makes it seem like another one of Jolie’s favorite Atelier Versace creations.
2012: Golden Globe Awards
It isn’t often Jolie wears color on the red carpet, so even the pop of red on her Atelier Versace dress at the Globes in 2012 was a welcomed surprise.
2011: The Tree of Life Premiere
Pre-2012, though, Jolie did embrace color just a bit more. Take this blood-orange, one-shoulder Jenny Packham dress she wore to The Tree of Life premiere.
2011: Cannes Film Festival
Jolie looked gorgeous in a rich, chocolate brown Atelier Versace gown at The Tree of Life premiere during the Cannes Film Festival.
2011: Golden Globe Awards
Seeing Jolie in this gorgeous, emerald green Atelier Versace dress has us wishing the actreess would start embracing color again.
2010: The Tourist Premiere
Versace changed things up when it came to their fabric choice, and put Jolie in a white, cashmere dress for the premiere of her film, The Tourist.
2010: Salt Premiere
A little black dress never goes out of style, and Jolie could easily wear this sequin Versace mini to an event today.
2009: Academy Awards
While originally, this Elie Saab dress was presented on the runway in white, Jolie had it made in black for the 2009 Oscars.
2009: BAFTA Awards
Jolie loves to throw just a hint of color into a look, and at the 2009 BAFTAs, she embraced neon yellow with the help of this Armani Privé midi dress.
2009: Screen Actors Guild Awards
While the front of this Max Azria dress was pretty simple, the open back provided some necessary intrigue and allowed the actress to show off her tattoos.
2009: Golden Globe Awards
Jolie wore a silver Atelier Versace dress with a slit to the Globes in 2009.
2008: Kung Fu Panda Premiere
A pregnant Jolie posed with her costar, Jack Black, at the premiere of Kung Fu Panda at the Cannes Film Festival in a green, Max Azria atelier gown, which showed off her baby bump.
2008: Screen Actors Guild Awards
Jolie’s love for vintage is nothing new. Back in 2008, she wore a strapless, vintage Hermes gown to the SAG Awards, which she attended with her then-boyfriend, Brad Pitt.
2007: Cannes Film Festival
Jolie expanded her color palette to canary yellow with a St. John gown, upping the glamour with a train and dramatic half-up ‘do.
2007: Golden Globe Awards
Once again in St John, Jolie attended the Globes, this time wearing a gray strapless dress with a matching shawl.
2005: The Good Shepard Premiere
The actress added a bit of sparkle to her repetoire, attending the premiere of The Good Shepard in an embellished Reem Acra dress.
2005: Mr. and Mrs. Smith Premiere
Clearly, Jolie was inspired by her character in Mr. and Mrs. Smith when she picked this leather, halter neck Versace dress for the premiere.
2004: Shark Tale Premiere
Jolie went for a more casual look for the Shark Tale premiere, pairing a cheetah print trench with jeans and red, pointed toe heels.
2004: Cannes Film Festival
The actress enjoyed another classic suiting moment at the premiere of Shrek 2 in 2004.
2004: Academy Awards
Jolie has always had a penchant for the classic movie star silhouettes, and the Marilyn Monroe inspiration of this Marc Bouwer is undeniable.
2003: Lara Croft: Tomb Raider – The Cradle of Life Premiere
The actress went simple for the premiere of the second Lara Croft film, attending the event in a brown, low cut dress with a gathered bodice.
2003: BAFTA Awards
Jolie looked gorgeous in a green, satin halter neck Colette Dinigan dress at the BAFTAs in 2003.
2002: Golden Globe Awards
Once again opting for a simpler look, Jolie attended the Globes in a black, strapless dress with her then-husband, Billy Bob Thornton.
2001: Lara Craft: Tomb Raider Premiere
Jolie really looked like Lara Croft when she attended the Tomb Raider premiere in a tank top and leather pants.
2001: Academy Awards
The actress’ exploration of menswear began years ago, when Jolie wore a white Dolce & Gabbana suit to the Oscars.
2001: Golden Globe Awards
Similarly, Jolie’s love affair with Versace is decades old, and she’s been wearing the brand since at least the 2001 Globes.
2000: Gone in 60 Seconds Premiere
Jolie once again went casual for a premiere, wearing a tee and leather pants while holding onto Thornton.
2000: Academy Awards
Looking very much like Morticia Addams, Jolie took home her first Oscar in a black, long-sleeved Marc Bouwer dress while on the arm of her brother, James Haven.
1999: Girl, Interrupted Premiere
Jolie attended the premiere of her film, Girl Interrupted, in a long, blue-ish gray coat with her hair pulled back.
1999: Screen Actors Guild Awards
A blonde Jolie attended the SAG Awards in a white, off-the-shoulder dress.
1999: Golden Globe Awards
Once again taking her brother as a date, Jolie attended the Globes in a sparkling Randolph Duke dress.
1998: Emmy Awards
The actress also wore Randolph Duke to the Emmys the year prior, arriving in a nude dress with a sheer, embellished skirt detail.
1998: Golden Globe Awards
Jolie took home her first Globe for her role in George Wallace while wearing a silver, one-shoulder midi dress.
1998: BAFTA Awards
The actress attended the BAFTA Awards in 1998 with her then-husband, Jonny Lee Miller, while wearing a simple black dress and sheer over shirt.