Get Ready to Gasp Over the Most OMG Oscars Looks to Ever Hit the Red Carpet

See who hit the red carpet in gasp- and drool-worthy designs at the Oscars. From Demi Moore to Billy Porter to so many others, these celebrities stunned in OMG looks.

By Alyssa Morin Feb 08, 2020 1:00 PMTags
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There's cute and then there's drop dead gorgeous.

When it comes to celebrities sashaying along the Oscars red carpet, most play it safe with ensembles that are classic, regal and chic. And while that's not a bad thing, every now and then one of Hollywood's biggest stars will take things to another level.

We're talking gasp-worthy designs like Cher's iconique black outfit and larger-than-life mohawk headpiece in 1986. The unforgettable number, which consisted of a jewel-adorned bustier, a matching bedazzled skirt and glitzy shawl, was designed Bob Mackie.

"This was one of my favorite outfits," the legendary star previously told Vogue about the lewk. "I had the idea mostly because the Academy didn't really like me... They hated the way I dressed and I had young boyfriends so they thought I wasn't serious."

She added, "So I came out and said, 'As you can see, I got my handbook on how to dress like a serious actress.'"

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Another OMG fashion moment? Anne Hathaway's blush-colored Prada dress. Dubbed the "nipple dress," the feminine gown was all anyone could talk about. And of course, how could anyone forget the 2001 ceremony when Björk stepped onto the carpet with her swan dress.

OMG, indeed!

With the 2020 Oscars upon us, we can't wait to see what our favorite celebrities slip into for the special occasion. Until then, take a look at our gallery below to see all of the swoon-worthy style to hit the red carpet.


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.


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.

Cynthia Erivo

The Harriet star is known for pushing the style boundaries, and this custom white-hot Versace dress was no different!

Kate Winslet

The Oscar winner brought the wow factor to the 2016 show with her melted lava-like silk lamé design by Ralph Lauren. From its black holographic color to the flowy train and curve-hugging structure, Kate shut it down on the red carpet.


The legendary star brought the glitz and the glamour to the 1988 event with her showgirl-like number. From her jewel-adorned bustier and matching skirt to the dazzling fringe beads to the see-through material, this is one unforgettable lewk.

Anne Hathaway

Believe it or not, this blush-colored Prada dress caused an uproar...but that's what makes it oh-so memorable. Dubbed the "nipple dress," this feminine design caught everyone's attention for its interesting structure.

Goldie Hawn

Who says a little black dress has to be boring? In 1987, Goldie Hawn dazzled in a shimmery black low-cut gown that featured silver accents.

Tiffany Haddish

The comedian paid homage to her late father by wearing a traditional African gown, which was also a nod to her Eritrean heritage. "I'm wearing an Eritrean, authentic princess dress," she told E! News at the time. "And I'm PROUD of it."

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