In early 1999, Jolie appeared in a glitzy, curve-skimming halter dress, setting off a series of neutral-hued but attention-grabbing red carpet looks.
Angelina Jolie in Randolph Duke at the 56th annual Golden Globe Awards in Beverly Hills, California, January 1999. Photo by Jim Smeal/WireImage.
Looking very early-naughts in an ivory suit, Jolie experimented with the menswear trend in 2011.
Angelina Jolie in Dolce & Gabbana at the Academy Awards in Los Angeles, California, March 2001. Photo by KMazur/WireImage.
She’s always had a penchant for the classic movie star silhouettes, though. They say if you dress the part…
Angelina Jolie in Marc Bower at the 76th annual Academy Awards in Hollywood, California, February 2004. Photo by Frazer Harrison/Getty Images.
This year’s Cannes Film Festival red carpet was all about the canary yellow gown, but Jolie proves she’s a decade ahead of the curve.
Angelina Jolie in Emanuel Ungaro at the premiere of Ocean’s 13 at the 60th annual Cannes Film Festival in Cannes, France, May 2007. Photo by Pool Benainous/Hounsfield/Legrand/Gamma-Rapho via Getty Images.
A hint of that brief flash of color showed up again two years later on the red carpet of the British Academy Film Awards.
Angelina Jolie in Armani Privé at the British Academy Film Awards in London, England, February 2009. Photo by Jon Furniss/WireImage.
The top-and-skirt gown combined with a matching velvet wrap gives the actress an older aura; she’s clearly the same red carpet presence as 10 years prior, but a bit more seasoned.
Angelina Jolie in Atelier Versace at the premiere of The Tourist in Madrid, Spain, December 2010. Photo by Getty Images.
A rare flash of color suits her — they say green is the toughest color, but Jolie pulls off this emerald tone with verve.
Angelina Jolie in Atelier Versace at the 68th annual Golden Globe Awards in Beverly Hills, California, January 2011. Photo by Evan Agostini/NBC/NBCU Photo Bank.
Later the same year, Jolie stepped out in a blood-orange Jenny Packham creation. It’s her color period.
Angelina Jolie in Jenny Packham at the premiere of The Tree of Life in Los Angeles, California, May 2011. Photo by Gregg DeGuire/FilmMagic.
Jolie’s velvet, thigh-high slit Oscars gown stopped the red carpet in 2012; it still might be her best red carpet look ever. (And, once again, with velvet returning to the fore of fashion this year, Jolie proves she’s way ahead of the fashion world.)
Angelina Jolie in Atelier Versace at the 84th annual Academy Awards in Hollywood, California, February 2012. Photo by Getty Images.
Every actress has a Saint Laurent tux phase, and Jolie’s hit around 2012.
Angelina Jolie in Saint Laurent at the British Academy Film Awards in London, England, February 2014. Photo by Getty Images.
While her previous “experimental” looks had involved a pop of color, here, Jolie opts for a rare sighting of pattern on the red carpet.
Angelina Jolie in Gucci Première at the world premiere of Unbroken in Sydney, Australia, November 2014. Photo by Getty Images.
… But for another premiere later the same year, it was back to business as usual in a sleek but conservative white cocktail dress.
Angelina Jolie in Ralph & Russo at the U.K. premiere of Unbroken in London, England, November 2014. Photo by Getty Images.
Though she frequently opts for a polished tumble of hair, here, Jolie keeps hair and makeup neutral, pairing a minimalist look with an equally minimalist Tom Ford gown.
Angelina Jolie in Tom Ford at the WSJ Magazine Innovator Awards in New York, New York, November 2015. Photo by Getty Images.
Classic, classic Angie returns for the premiere of her directorial effort — because even after 20 years of red carpets, some things never change.
Angelina Jolie in Atelier Versace at the premiere of By the Sea at AFI Fest in Hollywood, California, November 2015. Photo by Getty Images.