10 Best Oscar Dresses Of All Time

Unforgettable: Best Oscar Dresses of All Time Revealed

Did you know the average Oscar dress costs more than a new car? No joke. Some of these gowns are worth upwards of $100,000—and that’s before you add the jewelry! But let’s be honest, not every pricey dress is a winner. Some fade into fashion obscurity faster than you can say “Who wore it better?” While some others become the stuff of red-carpet legend.

With the stakes higher than a Meryl Streep acceptance speech, the Academy Awards have given us some of the most jaw-dropping, head-turning, and conversation-starting looks in Hollywood history. From classic elegance to daring risks (hello, plunging necklines), these 10 best Oscar dresses are the crème de la crème.

Audrey Hepburn’s White Floral Masterpiece (1954)  

Let’s start with the OG of Oscar fashion: Audrey Hepburn. Winning Best Actress for Roman Holiday, she floated onto the stage in a Givenchy gown that looked delicate, like woodland fairies stitched it. This tea-length dress had a subtle floral embroidery and remains to date one of the most unforgettable Oscar dresses of all time.

Cher’s Barely-There Bob Mackie (1986)  

When Cher arrived at the Oscars in a Bob Mackie creation that looked like an intergalactic Vegas showgirl costume, Hollywood blinked. Hard. Was it a dress? Was it performance art? Was it both? The black sequined number, complete with a feathered headdress could rival a peacock’s ego. Critics didn’t know what to do with themselves, but this bold choice is iconic decades later. Moral of the story? When in doubt, add feathers.

Halle Berry’s Sheer Elie Saab Stunner (2002)  

Halle Berry made history that year, becoming the first Black woman to win Best Actress, but her Elie Saab gown almost stole the spotlight. Almost. A deep burgundy, sheer bodice with strategically placed floral embroidery and a flowing silk skirt—it was equal parts daring and elegant. This gown is still referenced every awards season as the benchmark for “iconic.”

Lupita Nyong’o’s Cinderella Moment (2014)  

Lupita Nyong’o didn’t just walk onto the Oscars red carpet in 2014—she floated. Her powder blue Prada gown was so ethereal, that you half-expected her to be carried in by doves. The pleated chiffon creation featured a plunging neckline. Lupita described the color as “Nairobi blue,” a nod to her Kenyan heritage, and honestly, we’re here for it. She didn’t win an Oscar for Best Dressed that night (because that’s not a thing, sadly), but if it were? She’d have smashed it.

Jennifer Lopez’s Caped Wonder (2012)  

J.Lo is no stranger to jaw-dropping fashion, but her Zuhair Murad gown at the 2012 Oscars was next-level. The shimmering, body-hugging dress featured strategically placed cutouts and a cape that screamed “goddess.” It looked like it was designed to glow under awards show lighting—and glow it did.

Gwyneth Paltrow’s White Tom Ford Cape (2012)  

Speaking of capes, let’s talk about Gwyneth Paltrow’s Tom Ford moment. This minimalist The White gown with a built-in cape was so sleek and futuristic, that it made everyone else look overdressed. Critics called it “divisive,” but honestly? When has Gwyneth ever cared about what people think? Love her or roll your eyes at her Goop empire, this look was a game-changer.

Billy Porter’s Tuxedo Gown (2019)  

Yes, we’re including Billy Porter because history isn’t limited to gowns worn by women. When Porter arrived in a custom Christian Siriano tuxedo gown, the internet lost it. The top half was a sharp tuxedo jacket; the bottom half was a voluminous ball gown. It was bold, beautiful, and unapologetically queer in a space that traditionally sticks to rigid gender norms. Forget “Best Dressed” lists—this was a cultural moment.

Angelina Jolie’s Leg Moment (2012)  

Is it even possible to talk about Oscar dresses without mentioning Angelina Jolie’s black velvet Atelier Versace gown? The dress itself was stunning—structured, strapless, and classic—but it was that leg that became the night’s unexpected star. Angelina’s dramatic pose, with one leg jutting out like it had its publicist, became one of the most meme-worthy moments in Oscar history. Who knew a limb could have such a career-defining moment?

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Rihanna’s Baby Bump Reveal (2023)  

Okay, technically this is recent, but Rihanna’s couture Alaïa gown from the 2023 Oscars deserves a spot on this list. The gown, deep black and skintight, was designed to highlight her growing baby bump, proving once again that Rihanna doesn’t just wear clothes—she owns them. Pair that with her effortless confidence, and you’ve got a look for the ages.

Honorable Mention- Elizabeth Hurley’s Safety Pin Dress (1994)  

Alright, technically this wasn’t at the Oscars, but it’s so legendary it deserves an honorary mention. Elizabeth Hurley showed up on red carpets in a black Versace dress held together by gold safety pins. It was equal parts punk and couture, and it made the world collectively gasp. If this dress didn’t inspire you to raid your sewing kit for fashion inspiration, are you even trying?

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The Legacy of Oscar Fashion

The Oscars are about more than just movies. They’re about moments—fashion moments, to be exact. Whether it’s a classic Audrey Hepburn silhouette that defines elegance or a full-blown Cher extravaganza that leaves us speechless, these dresses are more than outfits. They’re pieces of history. This was our edit of the best Oscar dresses of all time top 10. Do not forget to comment down below which according to you are the best Oscar dresses of all time!

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