Angelina Jolie's 27 best looks, from her most iconic red carpet moments to cool off-duty style

Angelina Jolie's best looks showcase her distinctive glam-yet-edgy style. The actress has been dazzling with her unique fashion sense throughout her decades-long film career, during which she has demonstrated a penchant for black gowns and relaxed tailoring.

Jolie secured her first role as a child alongside her actor father Jon Voight in the 1982 film Lookin' To Get Out. However, her acting career gathered pace during the 1990s, when she starred in the 1999 drama Girl, Interrupted - for which she won a Best Supporting Actress award at the Oscars. She then solidified her status, in the early 2000s, as a leading lady in the action thriller Lara Croft: Tomb Raider.

Memorably, Jolie appeared in the film Mr & Mrs Smith opposite actor Brad Pitt, with whom she went on to raise six children - including three who are adopted - and briefly marry from 2014 to 2019. The star was nominated for Best Actress at the Oscars for her role in the drama Changeling and appeared in the Disney blockbuster Maleficent. Additionally, she has gone behind the camera, writing and directing the war film First They Killed My Father.

There is a thread of edgy glamour that ties together Jolie's most head-turning looks, and in 2023 she unveiled her own fashion line Atelier Jolie. The A-lister is famously a fan of ensembles that feature plenty of black colour, leather material and masculine tailoring. However, she has also mixed things up from time to time with bright colours, floral prints and feminine detailing in outfits that channel classic Hollywood.

These are Angelina Jolie's most unforgettable fashion moments, from showcasing some of the best red carpet looks to demonstrating the power of a well-tailored suit.