1991
If you were after proof you can’t fake a pout like hers, then may we present you with a then 16-year-old Angelina, whose lips were just as full back then as they are today. The fresh-faced beauty posed up a storm during a photo shoot in 1991, which saw her wear minimal makeup; save for a dusting of trending baby pink eyeshadow over her eyelids.
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1999
Some eight years later, Ange had lopped off her locks into a ‘mom’ cut, and dyed lengths a copper hue, streaked with blonde highlights. But rather than age her, the cut accentuated her chiseled jawline and sculpted cheekbones. A lick of mauve lipstick (another big trend at the time) completed the look.
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2003
She certainly set hearts racing while walking the red carpet at the UK premiere of Lara Croft Tomb Raider: The Cradle Of Life. Chanelling her bad-ass character, Angelina reverted back to the dark side with jet black locks styled into a cascade of curls. Pencil thin eyebrows did little to frame her suffused smoky eyes, which played up various shades of grey punctuated by black liner.
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2004
And so began Angelina’s transformation into bona fide movie star. Big hair and big dress energy (BDE) to match, the actress brought her A-game during awards season in 2004. We’d love to glean her hairstylist’s tips on how to backcomb tresses to perfection, or her makeup artist’s tricks on achieving velvet matte skin from forehead to décolleté.
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2009
Flanked by then-partner Brad Pitt, Ange had every reason to smile at the 81st Academy Awards – after all, she’d been nominated for the Best Actress award. A dewy base and sculpted brows set the scene for what quickly became her signature red carpet beauty look – a swipe of winged eyeliner on her upper and lower lash line, paired with a glossy nude lip.
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2010
Angelina had bangs cut in ahead of the UK premiere of Salt at the Empire in Leicester Square, London. But while her freshly chopped side fringe struggled to stay put in the wind, her soft smize wasn’t going anyway. A pretty pink gloss drew attention to her forever luscious lips, while tightly rimmed liner had us homing in on her grey-blue eyes.
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2012
If someone tries to tell you to only play up one feature at a time when it comes to makeup – then defriend them immediately. You don’t need that kind of negativity in your life. Want proof? Angelina arrived at the 84th Academy Awards in 2012 wearing a bold red lip AND a smoky eye. If she can do it, then so can you.
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2017
At the New York premiere of First They Killed My Father, Angelina opted for chestnut locks and striking hot pink lips (which just so happened to perfectly match the photo wall). The film was the second Angelina had directed herself, after first making her directorial debut with Unbroken in 2014.
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2018
It felt a little like déjà vu in 2018, when Ange sported the same jet black locks she had some 10 years prior. Despite her fair complexion, she certainly seems to suit dark hair. Looking ever the sophisticate at the 75th Golden Globe Awards, this stylish updo featured plenty of texture and height at the crown, as well as a few loose strands left free around her face to prevent the look from feeling too ‘stuffy’.
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2019
In September, the Maleficent: Mistress Of Evil star stepped out at the film’s European premiere with lighter hair again (it seems she doesn’t stick to one hair colour for long), and a blotted down red lip. Stony faced expression optional.
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From the 90s 'til today, we look back on the actor's best beauty looks.
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