Each year, it can be easy to get lost in the famous razzle-dazzle that’s so synonymous with the Academy Awards, that we forget to take a look back in time at some of the event’s most memorable moments.

So often, Academy Awards outfits from years’ past hide extensive, fascinating stories behind their seams—and it never gets any less fun to dissect the Oscars fashion moments that have stood the test of time. Keep scrolling for some of the best ones. 

Cher in Bob Mackie (1986)

Of all the Oscars attendees who’ve made waves with fashion, Cher comes out on top. But it wasn’t always that way; when the multi-hyphenate performer began to receive acclaim for her acting work in the 1980s, she says the Academy initially didn’t take her seriously, and fashion became her form of rebellion. 

“[They] didn’t really like me… they hated the way I dressed, I had young boyfriends, and they just thought I wasn’t serious,” the superstar recalled in a 2019 interview with Vogue. “As you can see, I got my handbook on how to dress like a ‘serious actress’.” Eventually, she was recognised as one; she won the Academy Award for Best Actress for her performance in Moonstruck two years later. 

Zendaya in Valentino haute couture (2022)

Time and time again, Zendaya and her stylist, image architect Law Roach, have concocted red carpet looks that last in the memory. On paper, this Valentino ensemble could read as understated in comparison to some of her other megawatt looks, but there’s an important reference here. In 1998, Sharon Stone famously attended the Oscars in a purple silk Valentino skirt paired with a white Gap shirt, and 24 years later, Zendaya and Valentino designer Pierpaolo Piccioli created their very own homage to the watershed style moment. 

Nicole Kidman in Christian Dior (1997)

Some Oscars looks are worth their weight in fashion gold, and Nicole Kidman’s green Dior dress is one of them. For the 1997 ceremony, the actress and Vogue cover star stepped out in an embroidered silk gown by John Galliano, one of the designer’s first pieces at Dior before he became world-famous. Despite some taking aim at the colour of the dress, it’s since become one of the most famous ensembles in Oscars history and a watershed moment for iconic European fashion houses being worn to the ceremony. 

Chloë Sevigny in Yves Saint Laurent (2000)

Perennial cool-girl Chloë Sevigny is known for her idiosyncratic and boundary-pushing personal style. At the Oscars in 2000, her Alber Elbaz for Yves Saint Laurent dress was undeniably classic; Sevigny later explained that the legacy of being nominated for an Oscar that year, for the drama film Boys Don’t Cry, made her want to keep her outfit as enduring and timeless as possible. She said in a 2024 interview with Vogue: “I knew that the photo would probably come up for the rest of my life, so I wanted to do something more timeless.”

Hunter Schafer in Ann Demeulemeester (2023)

While the Academy Awards are a formal affair, the dress code at the exclusive Vanity Fair Oscars Party is famously more relaxed. Nonetheless, Euphoria’s Hunter Schafer still made headlines in this Ann Demeulemeester look, which featured a white skirt and a chest piece made from a long feather, a Demeulemeester design signature. Schafer’s look isn’t just visually enchanting, but technically, too; that long feather is actually made from leather, by leather artist Robert Mercier, who also crafted Zendaya’s wet-look Balmain bodice for the Venice Film Festival in 2021. 

Zendaya in custom Valentino (2021)

As much as Zendaya’s custom Valentino look at the 2021 Oscars was authentic to her own style, the Dune actress was actually channelling another multi-talented hyphenate from a different era. Taking to social media, the star's stylist, Law Roach, revealed the look was an homage to none other than Cher, whose ab-baring gowns were famously commonplace on her 1970s TV series The Sonny & Cher Show. 

Roach shared a photo of a near-identical one of Cher's looks on Instagram (albeit with the neck-tie replaced by Bulgari jewels in Zendaya's case), and with the caption: "Constant inspiration."

Björk in Marjan Pejoski (2001) 

It seemed like the ultimate punk act at the time, but Björk has revealed that her 2001 Oscars dress, by designer Marjan Pejoski, was an homage to famous Hollywood actress and diver Esther Williams. She said in 2007: “[Journalists] wrote about it like I was trying to wear a black Armani and got it wrong, like I was trying to fit in. Of course I wasn’t trying to fit in.”

Gemma Chan in Valentino (2019)

Gemma Chan’s spellbinding pink Valentino Haute Couture dress also had covert qualities. Inside the voluminous composition, there were hidden pockets where the Crazy Rich Asians actress could stow away snacks (for her, cookies) during the notoriously long show. Chan told Entertainment Tonight on the red carpet: “It’s a long ceremony… you don’t get dinner.”

Gwyneth Paltrow in Ralph Lauren (1999)

There’ll always be a place in Oscars lore for Gwyneth Paltrow’s princess-like Ralph Lauren dress, worn to the 1999 ceremony. While it was criticised at the time for its loose fit (unfairly so, in our opinion), it’s easily one of the most memorable in Oscars history. The actress later revealed that the Harry Winston necklace she loaned for the night was later purchased by her late father, Bruce Paltrow, who gave it to her to wear at her wedding. 

Gwyneth Paltrow in Calvin Klein (2000)

Following the media attention from her winning dress the year prior, Paltrow kept things simple at the 2000 Oscars in this Calvin Klein slip. In a 2014 Goop interview, she said: “It’s an okay dress, but not Oscars material. I chose it because I wanted to disappear that year.” In 2020, she auctioned the dress to fundraise for those affected by Covid-19.

Halle Berry in Elie Saab (2002)

Halle Berry’s Academy Award win for Monster’s Ball was always going to be a big moment—it was the first year that two Black actors, Berry and Denzel Washington, had taken home both leading awards. For the night, she chose a dress by then-new designer Elie Saab.

Aside from being a career-making moment for the Lebanese couturier, the dress helped change expectations of what stars could wear on the once-conservative Oscars red carpet. 

Hilary Swank in Guy Laroche (2005)

There are striking red carpet dresses, and then there’s Hilary Swank’s navy Guy Laroche dress at the 2005 Oscars, instantly recognisable for its backless design. However, Swank was actually meant to wear a Calvin Klein dress on the big night that was swapped last-minute, meaning this famous moment may never have come to be. 

Per the New York Times, Swank had been consulting with the American brand for two weeks on the dress before changing her mind. A senior vice president of Calvin Klein said: “We wish it could have been our dress, but sometimes this happens. At the last minute, she said this is really what she wanted to wear today.”

Lady Gaga in Alexander McQueen and Tiffany & Co. jewellery (2019)

Attending the 2019 Oscars, the A Star Is Born actress wore a custom dress by Alexander McQueen, but the kicker was the ‘Tiffany Diamond’ necklace—featuring a $30 million gem that came with its own security detail, which shadowed Gaga for the entire night. In 2020, she told Graham Norton a security truck stopped her limo on the way to an after-party, and she was kindly asked to take off the necklace and return it to safe hands. 

Lupita Nyong’o in Prada (2014) 

The blue hue of Lupita Nyong’o’s Prada gown at the 2014 ceremony was a nod to her home city of Nairobi, Kenya, and the finely-pleated skirt had the intention of making the 12 Years a Slave actress appear as though she was a glass of bubbling champagne.

Natalie Portman in Dior Haute Couture (2020)

Look closely at the lapel of Natalie Portman’s Dior Haute Couture gown at the 2020 Oscars, and you’ll see the first names of female directors she felt had been snubbed by The Academy in that year’s ‘Best Director’ nominations; a category devoid of any women. 

Selma Blair in Ralph & Russo (2019)

After being diagnosed with multiple sclerosis, actress Selma Blair made a return to the red carpet at the 2019 Vanity Fair Oscars Party, radiating glamour in this bespoke gown by couturier Ralph & Russo. Blair could be seen crying in front of the cameras as a result of her elation to be back, telling paparazzi: “It took a lot to come out here.”

Julia Roberts in vintage Valentino (2001)

At a time when vintage fashion wasn’t a trend like it is now, Julia Roberts was way ahead. To collect her Oscar for Erin Brockovich in 2001, the actress picked a 10-year-old Valentino gown with a unique white V-shaped neckline.

The designer, Valentino Garavani, admitted to the dress being one of the proudest moments of his career, and said in an interview with The Telegraph: “I have to be sincere. The person that made me feel so very, very happy was Julia Roberts. When she got the Academy Award for Erin Brockovich I watched it on television and really, I was so excited that she appeared in my dress.”