Best Oscars Looks Of All Time

Update: The Oscars were held in person on Sunday, April 26 — and the red carpet was full of top-tier fashion moments. See which looks from the occasion made our best-of-all-time list ahead.

This story was originally updated on April 23, 2021.

The finish line is in sight! A-listers have glammed up for the Golden Globes, mellowed out for the SAGs, and pulled out almost all the stops for the Grammys (albeit mostly from the comfort of their homes). But the mother of all award shows will always be the Oscars, and it's but a few short days away.

The sartorial brainstorming has begun for who’s going to be wearing what on Sunday night: Will Cynthia Erivo arrive in Valentino Haute Couture? Will we get another Vanessa Kirby in Gucci moment for the record books? Is it Oscar de la Renta for Mank's Amanda Seyfried? All we can do is wait and see.

In an effort to help pass the time between now and Sunday night, we're taking a trip down memory lane and reminiscing on the best red carpets of Oscars past. See which celebrities made the cut by clicking through the throwback looks ahead.

Audrey Hepburn, 1954

It never took much to make the late Audrey Hepburn look glamorous, but in this Givenchy gown, Hepburn, glowing from winning an Oscar for Roman Holiday, is nothing short of perfection.

Audrey Hepburn in Givenchy.Photo: NBCU Photo Bank/Getty Images.

Grace Kelly, 1955

Designed by arguably the most famous costumier in history, Edith Head, Grace Kelly's Oscars look was, like most Grace Kelly looks, an absolute winner.

Grace Kelly in Edith Head. Photo: Silver Screen Collection/Hulton Archive/Getty Images.


Madonna, 1991

Dripping in Old Hollywood glamour, there's nothing we'd rather see Madonna wearing to the 63rd Annual Academy Awards than this Bob Mackie ensemble.

Madonna in Bob Mackie.Photo: Ron Galella/WireImage/Getty Images.

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