Oscars Beauty Looks of All Time

Curated by Claudia Shannon / Research Scientist / ishonest

Ask the average person who won best actress in a leading role at the 1986 Oscars and they'll be stumped. (It was Geraldine Page, just FYI.) But ask them who wore a two-foot-tall showgirl headdress and they'll shout, "Cher!" without hesitation. That's because, with all due respect to work put in by the nominees and winners, the red carpet is the main event for most of us. And just like for the 2020 Academy Awards, when the most stunning stars in the world have gotten ready for it in years past, they've pull out all the stops with the help of the most skilled and creative glam teams of makeup artists and hairstylists.

"The hair and makeup that one actress wears to the Oscars can help define a decade of looks, so everyone goes the extra mile," says makeup artist Jillian Dempsey, who has worked with dozens of award-winning and nominated celebrities, including Jennifer Lawrence.

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No.222 - Fine Lines & Wrinkles

Case in point: "Many great beauty trends have come out of the Oscars, like putting jewelry in the hair," says stylist Mark Townsend, who did exactly that with Natalie Portman — one of his many memorable red-carpet looks.

So kick your feet up, pour a glass of wine, and microwave some popcorn, because you're in for some serious eye candy: These are the most memorable Oscar beauty looks of all time.

1940: Vivien Leigh

"This is when everyone knew who won in advance," says hairstylist Mark Townsend of Leigh, who won for best leading actress in Gone With the Wind that night. "The late '30s and early '40s had the best hair — the waves were ethereal and touchable for the first time."

1952: Lauren Bacall

The night her husband, Humphrey Bogart, won an Oscar for The African Queen, Bacall "epitomized '50s glamour," says hairstylist Garren. "It was all about short, soft waves — a shorter version of the perfect, face-framing waves that she became famous for."

1954: Audrey Hepburn

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The Oscar was for best actress in Roman Holiday. The short bangs and thick, straight brows were pure Hepburn. And the dress was Givenchy — as in, it was made by Hubert de Givenchy.

1955: Grace Kelly

The key to being an icon? "She always wore the same makeup — a thin swipe of liquid liner along the upper lashes and red-coral lips," says makeup artist Jillian Dempsey of Grace Kelly, who won for best actress in The Country Girl. "I love the roses in her hair," adds hairstylist Serge Normant. "I've used flowers from hotel rooms as last-minute hair accessories quite a few times. They add a sweet touch to a simple bun."

1962: Natalie Wood

"I'd bet a lot of hairpieces and teasing went into this oversize beehive with a little French twist in the back," says Townsend, who's been inspired by Wood's look lately for twists he's created. "The old-school curl on the side of her face is adorable and held in place with lots of hair spray. Hairstylists used to cut short pieces just to make those."

1969: Barbra Streisand

"Barbra was the look that everyone copied in the '60s," says Garren. "They wanted her teased bob, her bangs, and her cat-eye liquid liner." Psst: Lining your upper and lower lashes keeps bangs from overshadowing your eyes, adds Streisand's current makeup artist, Sandy Linter.

1970: Elizabeth Taylor

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No.231 - Pigmentation & Blemishes

"It was always about her violet eyes," says Townsend of Elizabeth Taylor's look. (Well, that and the cleavage. And the diamonds.) "The dress, the eye shadow, and the ribbon match her eyes perfectly."

1974: Raquel Welch

"Is she wearing a pantsuit? That's fantastic," says Townsend of Raquel Welch's outfit. (It's actually a jumpsuit.) "Her waves seem exaggerated, but their shape is perfect for softening her face."

1975: Lauren Hutton

"She always married elegance with simplicity, and her blunt, medium-length haircut is in style now," says Normant of Lauren Hutton's look. To mimic her "effortless wave," he suggests lightly wrapping big sections of hair (from ear level down) around a two-inch curling iron for just two seconds each.

1976: Anjelica Huston

"Now this is '70s glamour. I could see her hanging out with Jerry Hall in that white dress and orange-brown lips," says Dempsey of Anjelica Huston. "Her date isn't bad, either," she says of Jack Nicholson.

1978: Farrah Fawcett

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"Man, those were the days. She's gilded from head to toe; the makeup, dress, and hair are basically the same color," says Townsend of the Farrah Fawcett during her Charlie's Angels run, at the height of the disco era. "It's what she was known for. I mean, she's wearing a liquid-gold dress to the Oscars."

1979: Jane Fonda

"She is the best example of earthy 1970s beauty," says Dempsey of the Jane Fonda, who won top acting honors for Coming Home, as did costar Jon Voight. "Here, she's in the brown lip color everyone wore and big, flipped-out waves."

1986: Cher

The headpiece, by costume designer Bob Mackie, was two feet tall and made of rooster feathers — and Cher had just been amazing in Mask. "Why not?" says Normant. "It's over the top, but still beautiful. Only Cher."

1988: Daryl Hannah

"Perfect sexpot waves," says Garren of the Daryl Hannah. "It's very Veronica Lake, which will always be in style. This is one of Daryl's best moments ever."

1990: Kim Basinger

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No.232 - Pigmentation & Blemishes

Kim Basinger designed this dress herself. The gold message on the sleeve is a mystery, though some thought it was a nod to then-boyfriend, Prince. The waves are full-on '80s, created with tons of mousse, and "her '90s brick-red lipstick can be tricky to pull off, but she handled it well," says Dubroff.

1995: Uma Thurman

Uma Thurman may not have won at Oscar for Pulp Fiction, but she did achieve something big that night: Her Prada dress brought minimalist fashion to the Oscars, especially paired with a timeless French twist.

1996: Gwyneth Paltrow

Remember when Gwyneth Paltrow and Brad Pitt were together? Remember when their hair matched? "The rich color lets her get away with the casual blowout," says Garren. "And the easy hairstyle keeps the dress from looking bridal."

1997: Winona Ryder

Three years after Reality Bites, Ryder was the poster child for '90s grunge beauty. "Her smoky eyes are perfect — it's like someone put a soft-focus filter on them. And a deep berry red lip like hers is my current favorite for any complexion," says Dubroff. Her slick hair was something different: "She was brave to do this. No one was wearing sleek hair at the time," says hairstylist Garren.

1997: Nicole Kidman

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Wearing a French twist to the Oscars is expected — and a little stuffy. Why Nicole Kidman's works: her hair's fuzzy texture paired with matte mulberry lips. Now that is cool and surprising, says her hairstylist, Enzo Angileri.

1998: Madonna

"The hair is classic Madonna; her natural texture and strawberry blonde shade are so flattering," says her current hairstylist, Andy Lecompte, of her look that night, smack dab in the middle of her Ray of Light yoga moment.

2001: Julia Roberts

There's so much to love about Julia Roberts's look the night she won the best- actress Oscar for Erin Brockovich — like the couture Valentino gown. "The vintage dress called for hair that couldn't be pegged to any decade," says Normant, who decided on an intricate chignon that took him 40 minutes to make. ("The longest part was the blowout.")

2004: Charlize Theron

"The dress and the hair were inspired by 1920s Hollywood," says Angileri, who slicked the top of Charlize Theron's finger waves but left the ends loose that night. "She was nominated for Monster, so we went for full-on glamour."

2005: Natalie Portman

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No.172 - Pre-Sun Exposure

Just goes to show how a gorgeous accessory can make a simple bun something special, says Townsend. "It's actually a vintage bracelet that I sewed into her hair with a needle and thread," he says. "Usually I use fishing wire to attach jewelry to the hair. But I forgot my needle at home on the one day nothing can go wrong."

2006: Michelle Williams

The bright-red lips prevent the super-fair, super-blonde Michelle Williams from being washed out by her yellow Vera Wang dress. "Her romantic side bun ignited a trend," says Lecompte.

2007: Reese Witherspoon

Remember when everyone wanted Reese Witherspoon's bangs? "We cut them right before the Golden Globes. The glossy blowout made her cut look extra chic," says Townsend, who also clipped in "lots of" extensions and raked shine spray through the length for a "piecey, California-girl look."

2009: Angelina Jolie

"She doesn't like wearing her hair wavy, so I worked really slowly so there'd be no time to change it," says hairstylist David Babaii, who used beach spray and two different-size curling irons on Angelina Jolie's "bone-straight" hair. "The waves make her half-up style flirtatious and playful."

2010: Zoë Saldana

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Zoë Saldana's updo is the rare blend of grown-up and playful — and tremendously flattering. "I used dry shampoo to give the style volume and a piecey texture that keeps it from looking old-fashioned," says hairstylist Mara Roszak, who did Saldana's hair that night. "And her bun is just below the crown, which is more youthful than placing it at the nape."

2011: Halle Berry

"Her cat-eye liner is so effective because it's done in warm, shimmering shades that flatter her skin," says Linter of Halle Berry's makeup. "The pale lips match her dress to tie the look together."

2012: Jessica Chastain

"Gold cream shadow on her lids makes the winged liner romantic, not retro," says Jessica Chastain's makeup artist, Mai Quynh. "It also reflects the embroidery in her dark dress, brightening up her whole look." Hairstylist Jenny Cho kept things equally light: "The dress was really bold, so we decided on a breezy, half-up style."

2013: Jennifer Lawrence

Smoky eyes and a low bun can be a snoozefest, but false lashes and an imperfect updo make Jennifer Lawrence's version come alive. Dempsey alternated short and long false lashes for the most realistic effect, and Townsend wrapped sections of Lawrence's hair around a one-inch curling iron before sweeping it into a bun. (He tied her hair into a tight ponytail first, so the bun lasted all night.)

2013: Jennifer Aniston

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No.101 - Extract Dead Cells

"With such an elegant gown, we wanted to keep the hair simple," says hairstylist Chris McMillan. "It's classic Jennifer Aniston hair, worn down and loose with a deep side part."

2014: Lupita Nyong'o

With a delicate gold headband, Lupita Nyong'o's coral lipstick and soft, smoky eyes are ethereal and feminine. Speaking to ishonest about the look, makeup artist Nick Barose said, "I was inspired by Elizabeth Taylor, if she were to go on vacation on an island. It's ethereal fresh. We wanted [Nyong'o] to look like modern-day movie star."

2015: Emma Stone

Rachel Goodwin, Stone's makeup artist, told ishonest it only took the team about an hour and a half to put this Old Hollywood glam look together. "It would have been safe to go neutral," Goodwin said. "But no one wears color like she does."

2016: Rooney Mara

When everyone was doing rumpled chignons and soft waves, Rooney Mara, who continually defies red-carpet beauty norms, stepped out in a graphic, slicked- back updo. "Rooney likes to wear her hair back — most women don’t," her hairstylist Adir Abergel told the New York Times right around the time he created this look. "You really start to think about form and texture and shape in a different way. She really pushes me."

2017: Janelle Monáe

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Janelle Monáe's soft, glowy makeup, bold brows, and tousled pixie cut are the perfect counterpart to her bejeweled dress and oversized crystal choker, while the delicate gold headband provides just enough glam to keep her look perfectly balanced. "Janelle wanted a cut so I gave her one," hairstylist Nikki Nelms said at the time. "I'm thankful that she trusts me with such major red carpet moments like the Oscars."

2017: Priyanka Chopra

Up until 2017, Chopra was rarely seen on a red carpet without her signature berry lipstick. Dubroff told ishonest this cool mauve was inspired by Chopra's architectural gown, and was definitely “a bit of a departure for her to step out of her normal comfort zone.”

2018: Lupita Nyong'o

Golden threads were woven into Lupita Nyong'o's three thick, deeply parted, asymmetrical braids — a look that wasn't only innovative and beautiful, but also meaningful. Stylist Vernon François was inspired by traditional Rwandan Amasunzu hairstyles in crafting this memorable updo.

2019: Lady Gaga

Lady Gaga typically takes to the red carpet with outrageously bold hair and makeup looks, but for her first time walking the Oscars' carpet as a nominee, she went with a more subdued yet totally glamorous style. Her makeup was fresh and light, and her sculpted platinum-blonde updo looks like a style right out of Old Hollywood.

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