Cher
Cher shined bright at the 1986 event wearing an electrifying design and headpiece. Bob Mackie created the legendary ensemble, which consisted of a jewel-adorned bustier, a matching bedazzled skirt and a glitzy shawl.
Jennifer Lopez
J.Lo hit the red carpet in an intricately embroidered number at the 1998 ceremony. While this isn't usually the star's go-to color or style, her risky design certainly paid off!
Halle Berry
In 2002, the star made history as the first and only Black woman to win an Academy Award for Best Actress. What's more? Her daring dress was worthy of an award as well as she entered the room wearing an Elie Saab design, which featured a sheer top with floral embroidery.
Gemma Chan
Perfectly pink! The Crazy Rich Asians star brought bright and bold fashion to the red carpet with her voluminous Valentino gown.
Barbra Streisand
The legend raised the fashion bar very high at the 1969 ceremony with her completely sheer two-piece, which sparkled just as brightly as her golden statue.
Sandra Oh
One word: Wow! The Killing Eve star slayed the red carpet with a one-of-a-kind gown at the 2020 affair. She showed up and showed out wearing a sparkly champagne-colored Elie Saab creation.
Geena Davis
Well, hello! The Thelma and Louise star made heads turn at the 1992 show with her white-hot design, which included an over-the-top train, corset top and long satin gloves.
Sarah Paulson
Dressed to kill! The American Horror Story star lit up the room at the 2019 event wearing a fun and flirty Brandon Maxwell gown.
Edy Williams
The Hollywood star made a dramatic style statement at the 1986 awards ceremony with her showgirl-like ensemble.
Taraji P. Henson
Always one to take a fashion risk, the Empire star shut down the red carpet with her daring Vera Wang design.
Angelina Jolie
An OMG lewk, indeed! The Maleficent actress wowed the crowd at the 2004 event with a halter satin gown that featured a plunging neckline. Designer Marc Bouwer was the mastermind behind the piece.
Gal Gadot
The Wonder Woman actress looked effortlessly chic in a Givenchy design that was both regal and risqué.
Björk
A fashion moment no one will ever forget. Björk made jaws drop at the 2001 ceremony when she hit the red carpet in her now-infamous "swan dress" by designer Marjan Pejoski.
Salma Hayek
Sometimes, less is more—literally! The Frida star sizzled on the red carpet with a peek-a-boo dress by Alexander McQueen at the 2017 event.
Kim Basinger
The Oscar winner stole the show with an eye-catching dress that featured a half-blazer, half-corset top, larger-than-life bottom and glittery gold details.
Kristen Wiig
The Wonder Woman 1984 star set the red carpet ablaze with her red-hot and theatrically ruffled Valentino design, which she paired with black leather gloves and gold-studded heels.
Nicole Kidman
Despite the late Joan Rivers hating this dress, it was a design that got the whole world talking. From its electrifying color, body-hugging silhouette and intricate embroidery, the haute couture Dior gown was just that...haute.
Madonna & Michael Jackson
The dynamic duo made heads turn with their flashy ensembles. Madonna exuded old-Hollywood glamour with her shimmery strapless gown and feather boa while the King of Pop donned one of his famous blazers.
Angela Bassett
The American Horror Story alum made the red carpet her runway. She stunned in a vibrant fuchsia gown that not only had a dramatic shoulder sleeve but a thigh-high slit and billowing train.
Demi Moore
The Ghost star left any and all basique clothes at home and opted for something a lot more risqué and daring in 1989.
Lupita Nyong'o
All that glitters is gold. The Oscar winner shined as bright as the flashing camera lights at the 2018 ceremony with her glimmery gold chainmail dress by Versace. The high leg slit and sash-like detail gave it extra oomph.
Billy Porter
The fashion icon struck a pose in a larger-than-life gown by Christian Siriano. It's safe to say all eyes were on Billy Porter at the 2019 function.
Céline Dion
The Grammy winner oozed with glamour at the 1997 affair, as she stunned in a couture creation by Chanel. From the plunging neckline to the explosion of jewels, Céline was a total knock-out!
Charlize Theron
The actress made a grand entrance while attending her first-ever Oscars show in 2000. She donned a fabulous tangerine-colored gown by Vera Wang, which was way more dramatic in the back.