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.

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.



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