A vast majority of red carpet beauty looks are pretty—and nothing more. They're some safe combination of classic updo or glossy waves, glowing skin, and maybe a nude or pink lip. But the stars ahead took major hair and makeup risks and with it came a big reward—a spot on our list of the most iconic red carpet beauty looks ever.
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1
Jennifer Lopez
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Jennifer Lopez's sleek and sculptural updo was the perfect pairing for her unusual minty green eyeshadow and coral-pink lipstick in 2003.
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2
Angelina Jolie
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While the rest of the world was looking at her leg pop, we were fixated on Jolie's glossy pink-red lipstick and bombshell waves. The actress had finally nailed effortless Hollywood beauty.
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3
Jennifer Aniston
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Aniston's famous hair was the talk of the town when she hit the Emmys red carpet in half-dreaded curls.
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4
Gwyneth Paltrow
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Smoky eyes with a grungy naked dress make perfect sense. But an updo with a side French braid? That was a hair look we never expected.
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5
Jennifer Lawrence
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The Hunger Games actress solidified herself as a beauty star to watch when she hit the film's premiere wearing a gold-threaded updo.
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6
Emma Stone
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Wearing peach is hard for anyone. A blonde-and-tan Emma Stone made it look effortless.
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7
Gwen Stefani
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The ever-experimental Stefani took Rockabilly hair for a spin in the early 2000s.
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8
Julia Roberts
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The dress wasn't the only thing that became instantly iconic when Roberts won her first Oscar. Her side-parted and sculptural updo is recognizable to hairstylists everywhere.
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9
Charlize Theron
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With 1920s waves, 1920s skinny-brows, and a 2004 spray tan—this is one of Theron's reigning red carpet looks.
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10
Rihanna
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A naked dress called for a major beauty moment in the form of glossy nude lips, perfectly smoky eyes, and a head wrap in the same glittering fabric.
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11
Lady Gaga
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Out of all the hair colors we've seen Lady Gaga wear, this yellow-and-blonde wig paired with Barbie-pink lips, smoky eyes, and bold brows is a buffet of beauty.
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12
Blake Lively
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Blake Lively singlehandedly revived boho braids when she wore this rumpled mixed-braid and flower pin at the 2011 premiere od The Green Lantern.
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13
Barbara Streisand
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Barbara Streisand at the 1969 Oscars wearing mod eye makeup and a blunt bob that still looks classic in 2018.
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14
Beyonce
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It's hard to say exactly who started the lob haircut trend. Actually, that's not true. It was Beyonce at the 2014 Grammy Awards.
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15
Lupita Nyong'o
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With a pale blue dress fit for a princess, Lupita Nyong'o's jeweled headband was the perfect beauty statement.
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16
Jennifer Lopez
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The only thing more hotly debated than the 2016 election is whether or not Jennifer Lopez's oversized curls at the 2002 Academy Awards were chic. For the record: we love them.
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17
Drew Barrymore
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There's nothing more '90s than Drew Barrymore's vampy red lipstick paired with choppy bangs and daisy pins.
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18
Natalie Portman
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Natalie Portman shocked the world when she debuted her shaved head at a film premiere in 2004.
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19
Madonna
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Madonna as Marilyn Monroe is almost as iconic as Marilyn Monroe as herself.
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20
Zendaya
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Zendaya's gorgeous long locs caused controversy—and sparked conversation—about the beauty of cultural hair.
Jenna Rosenstein is the Beauty Director at BAZAAR.com. While attending NYU, she held internships at Women’s Wear Daily, Bloomingdale’s, Harper’s BAZAAR (as Glenda’s intern!) and Allure, the latter of which she parlayed into her first job as the Beauty Assistant. She left Allure three years later as the Senior Beauty Editor, spent a few months at Refinery29 in the same title overseeing branded content, before finally landing back at BAZAAR to oversee all digital beauty content. When she's not testing every lipstick known to mankind, getting zapped by new lasers, or interviewing experts and celebrities, you can find Rosenstein re-watching Star Wars movies, reading books about new discoveries in science and health, and playing with her Bombay cat named Maddie.