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.
Angelina Jolie's best looks
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.
1. The floor-length black Oscars dress
Jolie ripped up the rulebook for the Oscars in 2000. The star picked up the award for Best Supporting Actress - for her breakthrough role in Girl, Interrupted - in a long-sleeved black gown by Marc Bouwer. However, she made sure to add some sparkle to the understated dress in the form of silver drop-down earrings and a cuff bracelet.
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2. The yellow Cannes gown
Jolie brightened up the red carpet for the premiere of Ocean's Thirteen at the Cannes Film Festival in 2007. Her strappy, floor-length yellow Chloe gown featured elegant ruching at the waist, and she wore her brunette locks up at the sides. Dopamine dressing at its best.
3. The silky floral midi-dress
Usually one to shy away from print, Jolie stepped out in pretty florals for a Hollywood women's lunch in Beverly Hills in 2004. The star wowed in the silky cream form-fitting midi-dress, which featured small cap sleeves. She accessorised with a matching red clutch bag and heels.
4. The slinky LBD
Jolie channelled her trademark edgy style at the photocall for the film Eternals in Rome, Italy in 2021. The star wore a midi-dress fashioned from wet-look leather material, that featured ruching at the neckline and a slight split at the back. She finished off her all-black ensemble with a pair of strappy heels.
5. The white Oscars gown
There was a Grecian vibe to Jolie's outfit for the Oscars in 2004. The star looked like a goddess in a white Marc Bouwer gown paired with a shawl made from the same silky material. She accessorised with layered necklaces and a glossy nude lip - an easy make-up look for the evening.
6. The cool leather jacket
Jolie always exudes a distinct edgy style when off-duty. The star opted for a long-line black leather jacket, which she paired with black jeans and black platform sandals, while out in Los Angeles in 1998. She kept the look simple by sweeping her hair up into a bun and wearing minimal make-up.
7. The elegant Dior gown
At the premiere of war drama First They Killed My Father in New York in 2017, Jolie looked elegant in Dior. The strapless, floor-length gown - made from a chic mink hue - featured elegant pleating and a full skirt. The star added simple silver jewellery and a berry pink lip, one of the best bold lipstick looks.
8. The black Oscars gown and emerald earrings
Jolie wore her go-to shade to the Oscars in 2009, at which she was nominated for a Best Actress award for her leading role in Changeling. The star stepped onto the red carpet in a black sleeveless Elie Saab gown for the important occasion but added a pop of colour in the form of a pair of statement emerald green earrings. Like all of the best Oscars red carpet looks, her gown oozed Hollywood glam.
9. The nude Emmys look
A neutral colour palette is a core component of Jolie's style, as demonstrated by her nude dress for the Emmy Awards in Los Angeles in 1998. The actress wowed on the red carpet in the form-fitting, floor-length Randolph Drake gown, which featured sparkly detailing. She finished off the look with a silver bracelet and elegant up-do.
10. The chic all-black combo
Jolie understands the power of a coat that you can throw over anything to smarten up a look. The star wore a long, woollen-tailored number to run errands in New York in 2013, which she paired with an all-black ensemble of a jumper, trousers and boots. She accessorised with a large quilted black Yves Saint Laurent tote and classic aviator-style sunglasses.
11. The silky halterneck frock
There was no missing Jolie at a Las Vegas film industry lunch in 2005. The actress looked radiant in a silky halterneck cream midi-dress that featured a colourful geometric print design. She finished off her ensemble with a bouncy blow-dry and nude open-toed heels.
12. The show-stopping Versace gown
One of Jolie's most memorable red carpet moments was at the Oscars in 2012. The actress looked every bit the Hollywood star in a black Versace gown. The sleeveless dress featured a head-turning structured shape, including a daring thigh-split. She finished off the dramatic look with black open-toed heels and smokey eye make-up. And of course, a signature red lip.
13. The silver mesh gown
Jolie's stunning Versace dress, to attend the premiere of the film Eternals in Rome, Italy in 2021, was designed to look like molten silver. The sleeveless mesh gown was elegantly gathered at the waist, and the star finished off the striking ensemble with silver platform heels, sleek locks and glowy nude make-up.
14. The Mr & Mrs Smith leather look
All eyes were on Jolie at the Los Angeles premiere of Mr & Mrs Smith in 2005, the film set where she famously met her now-ex-husband Brad Pitt. The star wore a black leather halterneck dress by Versace, which she paired with voluminous swept-back hair and silver earrings.
15. The tuxedo-inspired gown
Jolie fused two of her favourite fashion looks - tuxedo-inspired tailoring and a dramatic black gown - for the London premiere of the film Eternals in 2021. The star wore a white shirt and black blazer jacket, with a voluminous black skirt, and she kept her hair and make-up polished but minimal for the evening out. Who said tuxedos for women need to be paired with trousers?
16. The relaxed beige suit
We love a chic tailored look with a twist, and Jolie exuded easy-going style in a relaxed beige blazer and matching wide-legged trouser set while out in New York in 2023. The star accessorised her trouser suit with large black sunglasses, pink patent footwear and a patterned tote bag.
17. The sequinned silver dress
Jolie dazzled in silver sequins at the Golden Globe Awards in 1999, where she won the Best Actress award. Her Randolph Duke floor-length dress was in a head-turning halterneck style, which featured a slight slit at the back. She finished off the ensemble with her hair in an elegant up-do and a pair of silver slip-on heels.
18. The flowing Balmain gown
Only Jolie could pull off a brown gown on the red carpet. The actress stunned in a flowing Balmain floor-length number at the Los Angeles premiere of the film Eternals in 2021. She paired it with chunky gold jewellery and a pair of pointed-toe heels.
19. The white Dolce & Gabbana suit
Jolie mixed it up with tailoring on the red carpet at the Oscars in 2001. The actress looked sharp in a white Dolce & Gabbana suit, featuring a buttoned-up blazer jacket and straight leg trousers. She finished off the look with her hair in an elegant bun and white heeled boots.
20. The flapper-style Ralph & Russo dress
Shimmering onto the red carpet for the premiere of the film Maleficient in Tokyo, Japan, Jolie looked like she had taken inspiration from classic 1920's Hollywood. Her silver flapper-style midi-dress by Ralph & Russo featured intricate fringing throughout. She accessorised with large silver earrings and a pair of patent silver heels.
21. The leather 'Lara Croft' trousers
Jolie is one of the few A-listers to successfully pull off black leather trousers on the red carpet. The actress wowed in a straight-leg pair, complete with a large belt, for the Los Angeles premiere of the film Lara Croft: Tomb Raider in 2001. She wore them with a simple black top and black-heeled boots.
22. The silk shirt and leather skirt combo
In a perfect smart-casual look, Jolie stepped out in a silky ivory-hued shirt and black leather pencil skirt combo for a New York film event in 2012. The star accessorised with bouncy locks, black patent heels and eye-catching emerald green jewellery.
23. The sweeping Versace gown
Jolie stunned on the red carpet at the Golden Globe Awards in 2012. In a departure from her usual style, the actress wore a silky white Versace gown, with a thigh-split, that featured a bright red neckline. She finished off her look for the glamorous Beverly Hills event with a red lip, matching clutch bag and white open-toed heels.
24. The feathered Golden Globes look
At the Golden Globe Awards in 2018, Jolie looked chic in a black floor-length ensemble. Her Versace gown featured sheer panelling, a small train and voluminous feathering on the wide sleeves. She wore her hair in a relaxed up-do and accessorised with silver earrings.
25. The regal Ralph & Russo gown
Jolie looked every bit the Hollywood princess at the premiere of Maleficent in London in 2019. The star sparkled in a white Ralph & Russo gown which featured a small train and extensive gold detailing. She wore her hair in a sleek up-do and added a bold pink lip.
26. The green Cannes maternity dress
In one of our favourite instances of red carpet maternity style, a pregnant Jolie stepped onto the Cannes red carpet for the premiere of Kung Fu Panda in 2008 in a gorgeous green dress. The flowing floor-length Max Azria gown perfectly showcased her bump as she walked alongside then-partner Brad Pitt.
27. The silky wrap dress
Jolie proved the classic wrap style makes an ideal elegant party dress. The actress attended the Hollywood Film Awards in Beverly Hills in 2017 in a grey silky floor-length number that featured long sleeves and a ribbon tie at the waist. She also amped up the glamour with a bright red lip.
28. The edgy BAFTAs suit
While dresses may dominate the red carpet, Jolie freshened things up with a trouser suit at the BAFTAs in London in 2014. The star paired a black blazer jacket with a white shirt and slim-fit black trousers. She finished off the relaxed tuxedo-style look with an undone black bow-tie and a pair of patent black heels.
29. The sheer midi-dress
Jolie looked elegant at a Disney event in Anaheim, California in 2019. The actress opted for a black midi-dress, that perfectly showcased her hourglass silhouette, and which featured sheer sleeves as well as a thigh-split. She finished off the look with dewy make-up and a pair of black heels.
30. The green Versace gown
Bright colours don't often feature in Jolie's wardrobe, but when they do, she goes bold - and often opts for green. At the Golden Globe Awards in 2011, the actress stepped out in a glittering long-sleeved, floor-length green Versace gown. She accessorised with smokey eye make-up and wore her hair in a sleek, voluminous style.
31. The off-shoulder BAFTAs look
Jolie stunned at the BAFTAs in London in 2018. The star wowed in a black velvet off-shoulder gown by Graff, which was designed to cinch in her waist and also featured a small train. She wore her hair in a sleek up-do - all the better to highlight her statement silver drop-down earrings.
32. The feathered white frock
At the Annual Critics' Choice Awards in Santa Monica, California in 2018, Jolie looked positively angelic. The actress stepped out in a white Ralph & Russo midi-dress, which featured statement feathering around the neckline and an asymmetric hemline. She finished off her look with a bright red lip and velvet nude pointed-toe heels.
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