Magnificent Fashion Moments: Angelina Jolie’s Style Evolution

Rocking a dark pixie cut, silver one-shoulder gown and heavy eye makeup, Angelina Jolie doesn’t quite hit the mark on the Golden Globes red carpet in 1998. At this point it was obvious the budding actress was testing the waters in finding her (style) groove, experimenting with different beauty and fashion looks in the process.

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Keeping her early love of sparkly gowns going, Angelina Jolie donned this stunning halter number to the 1999 Golden Globe awards, walking the carpet with her older brother, James Haven.

Side note: Remember when Jolie locked-lips with said brother?

Taking the win for Best Supporting Actress for her role in the 1999 flick, Girl, Interrupted, Angeline Jolie channeled her dark side for the red carpet in a fitted black gown and jet-black extensions to match. So why wasn’t anyone commenting on her poor choice of styling? Well, they might have been too busy reporting on the lengthy kiss Jolie shared with her brother James Haven as the pair posed for photos on the red carpet. We get sibling love, but this one was cringe-worthy.

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From glam to biker-chic, Angelina Jolie proves she can make it all work on the red carpet at the 2001 premiere of Lara Croft: Tomb Raider. In super-low-rise leather pants and a sleeveless crop-top, Jolie somehow pulls it off as fans everywhere begin to hunt for their own pair of second-skin trousers. The actress also sported a similar look to the premiere of Gone in 60 Seconds the year before, when she stepped out with then-boyfriend Billy Bob Thornton and showcased some heavy PDA with her bad-boy beau.

Never far from her date, Billy Bob Thornton, Angelina Jolie looks chic and timeless in a floor-length, strapless black gown, shawl and pearl necklace. More subdued than her usual style, Jolie looks like a classic beauty and easily wins a spot amongst the best-dressed of the night.

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No stranger to philanthropic pursuits, her time spent on the film Beyond Borders, which debuted in 2003, really set ablaze Angelina Jolie’s passion for helping others, as she ramped up her work in humanitarian causes. For the film’s premiere, Jolie stunned in a silky halter gown with her hair worn in soft, natural waves.

If we had to guess, we’d say Jolie’s glow and mega-watt smile here had something to do with her recent adoption of first child, Maddox, who Jolie noted at the time as being the biggest motivation behind her commitment to leading a less “self-destructive” life. Let's be honest, she's a single mom who is totally inspiring.

Seeming to almost glide along the red carpet, Angelina Jolie had onlookers picking their jaws up off the floor as she stepped out in a cream satin halter-style gown to the Academy Awards in 2004. Jolie accessorized her dress with matching shawl and a statement necklace, which complimented her risqué neckline.

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Sparking romance rumors from the start, fans watched for any sign of off-set chemistry between Angelina Jolie and (then-married) co-star Brad Pitt, as the pair stepped out for the premiere of Mr. & Mrs.Smith in 2005. Jolie looked every bit the femme fatale in a skin-tight leather gown.

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From the rumour-mill to real-life, Angelina Jolie and Brad Pitt made it official as a couple in 2006. Jolie’s style seemed to mature over these years into more classic and conservative styles, coinciding with her expanding family and cemented relationship status with Pitt.

Fun fact: Brad Pitt would be husband number three for Jolie, but it might have been number four if her long-standing relationship with model Jenny Shimizu in the late ‘90’s had panned out. Of her love affair with the model-actress that coincided with her first marriage to Jonny Miller, Jolie has said: "I would probably have married Jenny if I hadn't married my husband. I fell in love with her the first second I saw her."

Walking the red carpet in Cannes for partner Brad Pitt’s 2007 film, Ocean’s Thirteen, Angelina Jolie stunned in a bold yellow gown with a fitted bodice and ruched details.

For the premiere of Kung Fu Panda, a very pregnant Angelina Jolie, now considered the highest-paid actress in Hollywood, glowed as she walked the red carpet with partner Brad Pitt. The actress looked beautiful in an earthy-green gown.

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Cannes looks good on Angelina Jolie, who seems to save her best style moments for the luxe star-studded destination. This sheer blush-toned gown with draping details is easily one of our all-time favourite looks from Jolie, who absolutely nailed it with a bold red lip for some added contrast.

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For the 2010 premiere of her film Salt, Angelina Jolie expanded her style wheelhouse by stepping out in a bold red number with matching lip.

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Now a seasoned pro on the red carpet, Angelina Jolie had some fun with new styles at for the 2011 Golden Globe Awards, where she ventured outside her usual halter-gown style and opted for something with a little more coverage and a lot more colour. We loved the look, but we’re pretty sure only Jolie could pull it off.

For the 2013 premiere of World War Z, Angelina Jolie donned a white midi dress with a peplum waist. While it may not be the most glamorous look the actress featured that year, we love to see her continuing to experiment with her style and venture beyond floor-length gowns for red carpet occasions.

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In one of her most glamorous looks to date, Angelina Jolie rocked this floor-length, long-sleeve Elie Saab gown for the 2014 Academy Awards. She may not have taken home any hardware that evening, but there’s no doubt she won “best-dressed”.

Angelina Jolie rocked a tux like nobody’s business when she stepped out for the British Film Awards in 2014. This look definitely ranks as one of her best, and it’s so timeless, we could see this ensemble hitting all the same high notes in 2020.

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For the New York City premiere of First They Killed My Father in 2017, a newly-single Angelina Jolie opted for a strapless deep-lavender gown with pleats and soft chiffon trim at the bust. While Jolie would later describe these early years of her separation from Brad Pitt as some of the most difficult of her life, the actress never let it show in front of the cameras.

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Never one to leave us disappointed, the Maleficent — Mistress Of Evil star showed up for a photo call in Rome in 2019 wearing a striking purple pleat-detail top paired over black pants. Angelina Jolie is proof-positive that you should never stop experimenting — or having fun with — your personal style.

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