September 1998

For her appearance at the Emmy Awards in L.A.—where Jolie was nominated for Outstanding Lead Actress in a TV Miniseries for her role in Gia—the actress flaunted her boyish pixie-cut and mile-long legs.

March 2000

Few can forget Jolie’s ensemble at the Academy Awards that year. Upon receiving an Oscar for her supporting role in Girl, Interrupted, she delivered an intense, heartfelt speech while clad in a goth gown designed by Donatella Versace.

March 2001

Ever the style chameleon, Jolie made quite a stir in 2001 when she appeared on the Academy Awards red carpet wearing an all-white Dolce & Gabbana pantsuit.

June 2001

For the L.A. premiere of Lara Croft: Tomb Raider the actress seemed to borrow from the film’s wardrobe closet, opting for tough leather pants, black crop top, and killer black boots. Her tattoo collection served as her accessories of choice.

October 2003

Wearing a seafoam-green gown and tiny diamond earrings, Jolie showed off her softer side at the Beyond Borders world premiere in Madrid.

February 2004

Wearing a Marc Bouwer halter gown—complete with plunging neckline and matching silk wrap—the actress looked every bit the Hollywood star at the Academy Awards. H. Stern diamond necklaces added a decadent touch.

June 2005

At the L.A. Mr. and Mrs. Smith premiere, Jolie epitomized the modern-day femme fatale. The star worked the tough-luxe look of dark locks, leather gown, and a smattering of icy diamonds.

May 2007

The actress deviated from her usual somber separates by opting for a stunning canary-yellow Emanuel Ungaro gown for the Oceans Thirteen premiere at the Cannes Film Festival.

August 2007

During a day of shopping with the family in New York City, the actress/Red Cross ambassador/mom wore a chic and comfortable black three-quarter–length dress, nude leather ballerina flats, and oversize, Jackie O–worthy shades.