The Academy Awards have been around for more than 90 years, so it’s hard to pick the best Oscars dresses in red carpet history. There have been hundreds of show-stopping looks that have walked the red carpet at the Oscars, from fashion-forward fits, like Celine Dion’s backwards suit in 1999, to timeless looks, like Audrey Hepburn’s ballgown in 1954.
Still, we’ve narrowed it down to 25 of our favorite Oscars looks ever. As the 91st Academy Awards approaches (where Lady Gaga will definitely make history with another risk-taking look), we thought it was about time to look back at the Academy Awards outfits we can’t stop thinking of. There’s no doubt that the Oscars are Hollywood’s premier red carpet event, and with so much behind the Academy Awards, it’s no surprise why celebrities show up with their best black-tie attire.
The Oscars also mark the end of awards season, where celebrities who have spent the winter attending shows like the Golden Globes, SAGs and Grammys, show off their best red carpet look for a final hurrah. But which Oscars dresses will go down in red carpet history? We can’t say for sure, but we have feeling that these looks—from Reese Witherspoon, Cher and more—will definitely be up there.
Audrey Hepburn (1954)
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For the 1954 Oscars, where she won Best Actress for her role in Roman Holiday, Hepburn wore a white floral Givenchy dress with a boat neckline and a slim white belt. Hubert de Givenchy, who designed the dress, was one of Hepburn’s close friends, which is why she wore Givenchy to many of her major red carpets.
Grace Kelly (1955)
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When she won the Oscar for Best Actress for her role in The Country Girl in 1955, Kelly wore an ice-blue satin gown with matching gloves by costume designer, Edith Head.
Barbra Streisand (1969)
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Streisand accepted her award for Best Actress for her role in Funny Girl in 1969 in a sheer Arnold Scaasi pantsuit, which was accented with a white collar, a black bowtie and glitter.
Cher (1973)
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Cher’s look from the 1973 Oscars with Sonny Bono was nothing short of iconic. The Bob Mackie look included a gold, jewel-encrusted two-piece with an exposed midriff.
Farrah Fawcett (1978)
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Fawcett was the epitome of a Golden Girl at the 1978 Oscars when she wore this dripping-in-gold dress by Stephen Burrows.
Cher (1986)
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Cher shut down the Oscars red carpet in 1986 when she wore this Bob Mackie look, which included a sequins, gold, a spider-web-like bodice, a floor-length cape and an exposed midriff.
Gwyneth Paltrow (1999)
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When she accepted her Oscar for Best Actress for her role in Shakespeare in Love in 1999, Paltrow wore this pink Cinderella-like dress by Ralph Lauren.
Celine Dion (1999)
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Dion made red-carpet history in 1999 when she walked the red carpet in this backwards white tuxedo by John Galliano with shades, a ponytail and a matching hat.
Julia Roberts (2001)
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Roberts will be forever remembered for her black and white Valentino dress from the 2001 Oscars, where she won for Best Actress for her role in Erin Brockovich.
Halle Berry (2002)
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Berry became the first Black actress to win Best Actress in 2001 for her role in Monster Ball. For the occasion, she wore this semi-sheer Elie Saab dress, which featured a voluminous satin skirt with a floral bodice.
Charlize Theron (2004)
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Theron was pure glamour at the 2004 Oscars where she wore this Dior dress, which sparkled against her tan skin. She won Best Actress that year for her role in Monster.
Beyoncé (2005)
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Bey is known for her Grammys look, but this simple, body-hugging black Atelier Versace gown from 2005 Oscars is no joke. The singer accessorized the look with some chandelier earrings and a matching black clutch.
Hilary Swank (2005)
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No best Oscars dress list is complete without Swank’s backless navy-blue Guy Laroche dress. Swank won Best Actress that year for her role in Million Dollar Baby.
Reese Witherspoon (2006)
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Witherspoon looked timeless at the 2006 Oscars in this Christian Dior dress, which she wore as she accepted Best Actress for her role in Walk the Line.
Michelle Williams (2006)
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One of Williams’s most memorable fashion moments came at the 2006 Oscars when she wore this saffron gown.
Marion Cotillard (2008)
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Cotillard took mermaid dresses to the next level at the 2008 Oscars with this John Paul Gaultier dress, which was so embellished with crystals that it looked like fish scales. Cotillard won Best Actress that year for her role in La Vie en Rose.
Jennifer Lawrence (2011)
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For her first-ever Oscars in 2011, where she was nominated for Best Actress for her role in Winter’s Bone, Lawrence wore this red-orange Calvin Klein dress. Simple but classic.
Reese Witherspoon (2011)
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Witherspoon wore this black and white Armani Privé dress to the 2011 Oscars, which she accessorized with a bouncy, Barbie-like ponytail.
Angelina Jolie (2012)
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Jolie’s 2012 Oscars dress, a black Atelier Versace gown with a high slit, became an instant meme for how much leg it showed. But hey, if it works, it works.
Gwyneth Paltrow (2012)
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Paltrow looked regal at the 2012 Oscars, where she wore this Tom Ford look consisting of a cape with a white gown.
Lupita Nyong’o (2014)
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In honor of her home country of Kenya, Nyong’o described the color of this custom Prada dress as “Nairobi blue.” Nyong’o won Best Supporting Actress that year for her role in 12 Years a Slave.
Zendaya (2015)
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Zendaya’s 2015 Oscars look, a silver Vivienne Westwood number with dreadlocks, was shrouded in controversy after Giuliana Rancic criticzed the dress with a racist remark. Controversy aside, it’s still one of the most memorable looks to walk the Oscars red carpet.
Emma Stone (2017)
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When Stone won the Oscar for Best Actress for her role in La La Land in 2017, she stunned in this fringe Givenchy number.
Taraji P. Henson (2017)
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Henson stole the show at the 2017 Oscars when she walked the red carpet in this velvet Alberta Ferretti gown, with a high slit.
Saoirse Ronan (2018)
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For the 2018 Oscars, where she was nominated for Best Actress for her role in Lady Bird, Ronan wore this baby Calvin Klein dress with an oversized bow in the back. She complemented the look with a brand-new bob.
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