That’s not to say she hasn’t changed throughout the years in terms of appearance. However, Angelina’s cute pixie haircut and brown lipstick throughout her early career can only be described as a 90s wish come true. In a nod to Marilyn Monroe’s days in classic Hollywood, the actress also wore her hair in voluminous curls and a bold lip. In addition to her own style choices, Angelina is well-known for the instantly recognizable roles she has performed in movies like Maleficent and Girl, Interrupted, where she dazzled with dramatic red lips and high prosthetic cheekbones as the disturbed Lisa Rowe. The actress, filmmaker, U.N. ambassador, and mother of six has been spotted more recently sporting classic winged eyeliner, a subtle smokey eye, and chic updos or classic waves.

A 13-year-old attending the Oscars is just another day, right? On the red carpet for the Academy Awards, Ange snuggled up to her legendary actor father, Jon Voight, and her brother James. She quit acting classes at the age of 14, wanted to work as a funeral director, dressed entirely in black, dyed her hair purple, and spent her free time partying with her live-in partner. Ange, go. Ange began modeling two years later and even appeared in music videos for artists like Meatloaf and Lenny Kravitz before the acting industry called her back to Hollywood.

Angelina met British actor Jonny Lee Miller after appearing in Hackers, her first full-fledged Hollywood film, and they were married a year later while wearing black rubber leggings and a white blouse with his name inscribed in blood, no less. The actress wore a very adorable pixie crop and soft, cool-toned makeup during this time. Angie wore a stylish slicked-down pixie crop and a lot of blue eyeshadow when she walked the red carpet at the 1998 Golden Globes.

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