Audrey Hepburn
It’s easy to see where the current brow craze came from if you look back at Audrey Hepburn’s winning night where she picked up the Oscar for Roman Holiday in 1954.
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Grace Kelly
Image Credit: Photo Credit: Getty Images Even more than 60 years later, we could all take a cue from Grace Kelly in 1955, when she looked fresh-faced and youthful with coral-red lips and a rose-adorned updo.
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Elizabeth Taylor
Image Credit: Photo Credit: Getty Images Blue eyeshadow to match her blue gown (and a whisper-pink lip)—classic Elizabeth Taylor.
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Lauren Hutton
Image Credit: Photo Credit: Getty Images Lauren Hutton in 1975: the picture of natural-beauty perfection.
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Winona Ryder
Image Credit: Photo Credit: Getty Images In 1996, Winona Ryder looked like she stepped out of a time machine from the ‘20s, with her sleek retro waves and ultrafeminine makeup.
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Courtney Love
Image Credit: Photo Credit: Getty Images She may not stand out for the right reasons on every red carpet, but in 1997, Courtney Love stole the show with her perfect blonde bob, clean eye makeup and cherry red lips.
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Minnie Driver
Image Credit: Photo Credit: Getty Images The actress looked every bit the English rose with her dreamy, fairytale-worthy ringlets and burgundy lipstick that perfectly matched her gown.
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Penelope Cruz
Image Credit: Photo Credit: Getty Images Penelope Cruz apparently doesn’t age. In 2000 the classic beauty went minimal with her makeup and major with her bun. She glowed.
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Julia Roberts
Image Credit: Photo Credit: Getty Images When she won for Erin Brockovich in 2001, Julia Roberts literally turned heads—her woven updo was a piece of art.
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Gwyneth Paltrow
Image Credit: Photo Credit: Getty Images When she won for Shakespeare in Love, the actress went pretty in pink and it was great, but her edgier Oscar ensemble in 2002 won us over. Braids, smoky silver eyes, rosy lips—yes please!
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Halle Berry
Image Credit: Photo Credit: Getty Images With her fresh pixie and bronzy makeup, Halle Berry managed to make Oscar glamour look totally effortless in 2012.
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Natalie Portman
Image Credit: Photo Credit: Getty Images A headbanded beauty: Natalie Portman walked the red carpet in 2005 with a ballerina’s poise wearing a crystal headband and light, rosy makeup that gave her an inner glow.
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Gisele Bundchen
Image Credit: Photo Credit: Getty Images When she hit the scene with Leonardo DiCaprio in 2005, model Gisele Bundchen caused everyone to stop and stare at her cascading waves, bronzed complexion and barely there makeup.
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Michelle Williams
Image Credit: Photo Credit: Getty Images As Jennifer Lopez reminded us at this year’s Golden Globes, yellow and red are a stunning combination. Michelle Williams won the carpet when she pulled out all the stops for the ravishing combo in 2006.
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Marion Cotillard
Image Credit: Photo Credit: Getty Images Marion Cotillard proved that a formal occasion such as the Oscars doesn’t require an updo in 2008. Her chic side part and loose curls, along with clean makeup and a scarlet lip, was a classic.
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Jessica Chastain
Image Credit: Photo Credit: Getty Images Jessica Chastain circa 2012 wins for best cat eye and nude lip combo, a look that’s classic yet takes precision to actually pull off.
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Kerry Washington
Image Credit: Photo Credit: Getty Images In a sea of nude and bright red lips, Kerry Washington’s choice to go with a deep plummy raisin was bold and beautiful in 2014. Add to that luscious locks and you have a winner.
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Lupita Nyong’o
Image Credit: Photo Credit: Getty Images In 2014 Lupita Nyong’o singlehandedly made headbands cool again when she turned up on the Academy Awards’ red carpet wearing an elegant version that drew all eyes to her luminous complexion.
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Emma Stone
Image Credit: Photo Credit: Steve Granitz/WireImage At the 2017 Oscars, La La Land winner Emma Stone stepped out with vampy '40s-inspired waves and brick-red lips in a fresh ode to Old Hollywood glam.
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Margot Robbie
Image Credit: Photo Credit: Getty Images The Australian actress pretty much guaranteed her lipstick—Hourglass Opaque Rouge Liquid Lipstick in Raven—would sell out when she stepped onto the Oscars carpet in 2015 with the covetable pout and of-the-moment platinum blonde lob.