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It’s that time of year again: awards season. Beginning in February, it’s an exciting time for fans of the entertainment industry, and every win, loss, and social media post leads Hollywood to the final show, the Oscars. The 93rd Academy Awards took place April 25, and while plenty of discourse could be had about which actors were nominated and what films were snubbed, the main event is arguably the one before the event — the red carpet. 

The Oscars red carpet is something fashion lovers can look forward to; trends are often predicted, and small designers can get large exposure. Plus, it’s just fun. The annual awards ceremony has taken place since 1929, and it’s fascinating to see how fashion has both evolved and come full circle right in front of the paparazzi’s lenses. From outlandish to outstanding, the following are some of the most iconic fashion looks to be worn to the Academy Awards, listed in chronological order. 

Grace Kelly, soon to be Princess of Monaco, wore a stunning mint green gown by Edith Head to the 27th Academy Awards. She won Best Actress for The Country Girl, and looked every bit the part of a princess while doing so.

In 1969, Diahann Carroll looked absolutely ethereal while presenting in a light pink gown with a flowing, sparkly sheer overlay. It’s giving couture fairy godmother meets The Supremes elegance.

Serving looks at the Oscars is a pastime for Cher. While all of her head-turning gowns by Bob Mackie are iconic, 1988s beaded “naked dress” definitely stole the show.

Demi Moore went the DIY route for the Oscars in 1989. While the corset-bike shorts-gown trifecta has made its fair share of ‘worst dressed’ lists, it’s kind of a look? Very 80s. Shout out to Demi for being a crafty queen!

Are words even needed here? Madonna, an icon, wore Bob Mackie in the style of Marilyn Monroe, an icon, in 1991. She took Michael Jackson, an icon, as her date. It’s all very … iconic.

Yes, those are real American Express Gold cards. And, yes, Australian costume designer Lizzy Gardiner did make a dress out of the cards, and wore it to the 1995 Oscars. She won Best Costume Design, naturally.

Who could forget Céline Dion’s  drapey backwards suit by John Galliano for Christian Dior? Honestly, the sunglasses and the hat elevated the 1999 look.

Love it or hate it, there’s no denying that Björk’s 2001 Marjan Pejoski “swan dress” might just be the most notable Oscars look of all time. It’s been parodied by the likes of Miley Cyrus (or was it Hannah Montana?) and Ellen DeGeneres. And, Valentino even debuted an updated couture version in 2014 — minus the ostrich eggs.

Halle Berry wore a flattering burgundy Elie Saab gown to the 2002 Oscars. Not only did she look amazing, but she also made history that day, and became the first Black woman to win the Best Actress award.

Angelina Jolie’s 2012 Atelier Versace Oscars look may have sparked a meme, but the satin Marc Bouwer gown she wore in 2004 is the definition of timeless.

Known for her immaculate red carpet style, Fan Bingbing did not disappoint in a fuchsia Marchesa ballgown at the 85th Annual Academy Awards. It’s refreshingly bright, and the cut is both elegant and especial.

Pharrell pulled up to the 2014 Oscars in Lanvin tuxedo shorts … tuxedo shorts. It was a moment. (Try not to pay attention to the fact that he was also not wearing socks.)

Lupita Nyong’o has not had a single miss on the Oscars red carpet. Her 2015 pearl-covered custom Calvin Klein Collection dress further solidifies this fact.

Mandatory Credit: Photo by David Fisher/Shutterstock (10544110ev) Janelle Monae 92nd Annual Academy Awards, Arrivals, Los Angeles, USA – 09 Feb 2020

Billy Porter’s 2019 Christian Siriano tuxedo gown. That’s it. That’s the tweet.

Jason Momoa and Lisa Bonet coordinated in pale pink Fendi at the 2019 Oscars. The ‘fit itself was a statement, but the custom Fendi scrunchie on Momoa’s wrist truly pulled the look together.

Janelle Monáe’s 2020 hooded Ralph Lauren gown had 168,000 Swarovski crystals attached, and it took 600 hours’ worth of hand embroidery to apply them, according to WWD executive editor Booth Moore. The outcome? A glittering masterpiece.


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