The Oscars have always been more than just an awards night, it’s the ultimate fashion spectacle. Year after year, the red carpet transforms into a runway where Hollywood’s biggest stars bring their A-game, knowing their looks will be remembered long after the speeches and trophies. Some go for timeless elegance, while others take risks that either set trends or leave people wondering, ‘what were they thinking’?

From iconic ball gowns to sleek modern masterpieces, Oscar fashion has delivered some unforgettable moments. Think of Audrey Hepburn’s classic Givenchy dress, Cher’s daring Bob Mackie creation, or Lupita Nyong’o’s flowing blue gown that looked like it belonged in a dream. These outfits didn’t just turn heads on the red carpet, they became part of fashion history.

Not every risk has paid off, but the ones that did? Pure magic. Some celebrities have made effortless elegance their signature, while others have embraced bold colors, dramatic trains, and over-the-top embellishments. The Oscars are where fashion statements are made, and sometimes, one incredible dress can steal the entire show.

So, who really left a lasting impression? Which looks defined red carpet glamour and became legendary? Let’s take a trip down memory lane and revisit the best-dressed celebrities in Oscars history, the ones who turned a night of movies into a moment of pure fashion perfection.

27. Audrey Hepburn steals the show at the 1954 Oscars

Audrey Hepburn’s 1954 Oscars look is pure Hollywood magic, elegant, timeless, and still talked about decades later. Winning Best Actress for Roman Holiday, she stepped onto the stage in a dreamy white dress that perfectly framed her delicate features and signature collarbone. Most people credit Givenchy for the design, but here’s where it gets interesting.

Some believe it was the work of legendary costume designer Edith Head, originally created for the film and later altered for the big night.

Honestly, does it even matter? The dress, whoever designed it, became an instant classic. It wasn’t just about the fabric or the fit, it was the Audrey effect. She could’ve worn a paper bag and still looked like royalty. But this dress? It sealed her status as a fashion icon. Simple, chic, and effortlessly graceful, it set the bar for every Oscar look that followed.

26. Joanne Woodward brings her A-game at the 1958 Oscars

Joanne Woodward’s 1958 Oscars look proves that style isn’t about the price tag. While most stars rely on designer gowns, Woodward took a different approach, she made her own dress. Spending just $125 on fabric, she crafted a stunning green gown that looked just as glamorous as the high-end couture surrounding her.

Why go the DIY route? She simply didn’t expect to win. As she told the Associated Press (via Vanity Fair),

So I didn’t want to invest too much. Why, I’m almost as proud of the dress as I am the Oscar.

But fate had other plans. Winning Best Actress for The Three Faces of Eve, she walked up to accept her Oscar in a gown that was not only elegant but completely her own.

Paired with classic white gloves, the dress exuded timeless sophistication. Woodward later admitted she was just as proud of her creation as she was of the award itself. Her choice wasn’t just about saving money, it was a statement that confidence and personal style can outshine any designer label.

25. Cher and her Bob Mackie masterpiece at the 1986 Oscars

Cher doesn’t do boring, and her 1986 Oscars look proved it. Forget a gown, she arrived in a Bob Mackie masterpiece that was part showgirl, part warrior, and all drama. With a towering feathered headpiece, a sequined midriff-baring outfit, and a sheer cape, it was less “red carpet dress” and more “fashion mic drop.”

But this wasn’t just about turning heads. Cher, snubbed for her role in Mask, was making a statement. If the Academy wasn’t going to give her a nomination, she was going to make sure they noticed her anyway. And, well, mission accomplished.

Two years later, she won Best Actress for Moonstruck in another Bob Mackie creation, but nothing has ever topped the sheer audacity of her 1986 look. Love it or not, it remains one of the most unforgettable Oscar outfits of all time.

24. Nicole Kidman shows her bold side at the 1997 Oscars

Nicole Kidman’s 1997 Oscars gown was nothing short of a fashion revolution. Dressed in a chartreuse John Galliano for Dior creation, she turned heads with its sleek silhouette, high slit, and intricate floral embroidery. It was bold, unexpected, and instantly unforgettable.

But not everyone was ready for it. Joan Rivers famously heckled her on the red carpet, demanding, (via The Hollywood Reporter),

Nicole! Come tell me why you wore such an ugly color!

Oh, Joan. If only she knew that years later, this dress would be hailed as one of the greatest Oscar gowns of all time.

At a time when safe and sparkly ruled the red carpet, Kidman took a risk, and it paid off. The gown cemented her status as a true fashion icon, proving that sometimes, the most controversial choices end up being the most legendary.

23. Cate Blanchett and John Galliano team up for 1999 Oscars

Cate Blanchett’s 1999 Oscars gown wasn’t just a dress, it was wearable art. Designed by John Galliano, the ethereal creation featured delicate embroidery that seemed to bloom from her skin, as if the flowers were growing up her back. It was both whimsical and striking, an optical illusion of couture genius.

At the time, Blanchett was nominated for Elizabeth, a film full of regal, extravagant costumes. Compared to that, her slinky, effortlessly elegant gown felt almost understated, but in the best way possible. It was modern, dreamy, and unforgettable.

The fashion world certainly took note. The gown is now preserved in the Museum of Fine Arts in Boston, proving that some Oscar dresses don’t just make history, they become it.

22. Rita Moreno dazzles at the 1962 and again at the 2018 Oscars

Rita Moreno’s 1962 Oscars dress wasn’t just stylish, it became a symbol. Instead of turning to a big-name designer, she had it made from Japanese obi fabric while filming Cry of Battle in the Philippines. When she won Best Supporting Actress for West Side Story, the moment was historic, she became the first Latina actor to take home an Academy Award. The dress, with its striking brocade skirt, became just as legendary.

But the real flex? She wore it again 56 years later at the 2018 Oscars, proving that true style is timeless. While others search for the latest couture, Moreno simply reached into her closet and pulled out a piece of history. The fit was just as flawless, the confidence just as strong, and the impact even bigger the second time around.

Few could pull off re-wearing a decades-old gown on Hollywood’s biggest night, but for Moreno, it wasn’t just a fashion moment, it was a statement. Classic, bold, and unforgettable, just like her.

21. Björk’s swan dress steals the spotlight at the 2001 Oscars

Björk’s 2001 Oscars dress wasn’t just fashion, it was performance art. The Icelandic singer, known for pushing boundaries, showed up in a full-on swan dress by Marjan Pejoski, complete with a feathery neck draped around her own. Instantly, it became one of the most talked-about red carpet moments in history. Critics mocked it, comedians cracked jokes, and yet, Björk stood unbothered.

What many missed was that she knew exactly what she was doing. This wasn’t a case of accidental fashion chaos. She later joked referencing the fact that she literally pretended to lay eggs on the red carpet, (via Vogue)

C’mon, you don’t bring eggs unless you want to take the piss, right?

Love it or hate it, the swan dress did what few Oscar outfits ever do, it became unforgettable. While most stars aim for timeless elegance, Björk chose playful absurdity and made history in the process.

20. Julia Roberts proves less is more at the 2001 Oscars

Julia Roberts proved that less is more at the 2001 Oscars. Winning Best Actress for Erin Brockovich, she graced the stage in a black-and-white Valentino gown that oozed old Hollywood glamour. The best part? It was vintage, straight from Valentino’s 1992 collection, yet looked completely fresh and modern.

While some stars chase the latest trends, Roberts made a statement with classic simplicity. The sleek black velvet, contrasted with crisp white detailing, gave her a regal presence without trying too hard. No flashy embellishments, no over-the-top drama, just timeless elegance done right.

The dress became instantly iconic, not just because of its design but because of who wore it and how she wore it. Decades later, it remains one of the most celebrated Oscar gowns of all time, proving that true style never fades.

19. Halle Berry and her Elie Saab gown on the historic night of 2002 Oscars

Halle Berry’s 2002 Oscars dress wasn’t just stunning, it was history in the making. Winning Best Actress for Monster’s Ball, she became the first Black woman to take home the award, and her Elie Saab gown was just as unforgettable as the moment itself.

The dress was the perfect mix of elegance and daring. With a sheer, embroidered bodice and a rich, flowing burgundy skirt, it balanced classic couture with modern sexiness. Berry later admitted to Los Angeles Times,

I saw so many gowns, but this one just felt the part: classic, couture, modern and sexy.

And she wasn’t wrong, it became one of the most iconic Oscar looks ever. This wasn’t just a red carpet win. It was a fashion moment that symbolized a groundbreaking achievement. The dress, like Berry’s victory, still stands as one of the most powerful in Academy Awards history.

18. Michelle Williams’ bold look at the 2006 Oscars

Michelle Williams’ 2006 Oscar gown was a masterclass in unexpected elegance. Wearing a bold saffron-yellow Vera Wang creation, she turned heads with its delicate draping, plunging neckline, and soft, feathery detailing. It was risky, unconventional, and absolutely breathtaking.

What made the look even more iconic? The styling. Williams paired the gown with classic Hollywood waves and a striking red lip, proof that the right accessories can elevate a dress from beautiful to unforgettable.

Nominated for Brokeback Mountain, she brought the same quiet strength to the red carpet as she did to the film. Years later, her look remains a fan favorite, proving that sometimes, the boldest color choices create the most timeless fashion moments.

17. Lupita Nyong’o Nairobi Blue at the 2014 Oscars

Lupita Nyong’o’s 2014 Oscars gown was pure magic. Winning Best Supporting Actress for 12 Years a Slave, she floated onto the red carpet in a dreamy, custom Prada dress in a shade she called “Nairobi blue.” Soft, elegant, and effortlessly regal, the gown looked like it was made for a fairy-tale moment, fitting, since Nyong’o had just skyrocketed from rising star to Hollywood royalty.

With its plunging neckline and flowing pleated skirt, the dress felt weightless, almost as if she was gliding. It wasn’t just beautiful, it was breathtaking. Many still call it one of the most stunning Oscar dresses ever, and honestly, they might be right.

Some gowns are glamorous, some are bold, but this one? It was unforgettable. Nyong’o didn’t just wear a dress; she wore a moment in fashion history.

16. Emma Stone’s elegance at the 2017 Oscars

Emma Stone took home her first Oscar in 2017 for La La Land, and she dressed like a winner, literally. Her gold Givenchy gown, shimmering with intricate beading and layers of fringe, made her look like a walking Academy Award.

The dress was pure Old Hollywood glamour with a modern twist. The vintage-inspired silhouette, the delicate sparkle, and the effortless movement of the fringe made it a standout moment on the red carpet. Adding to the significance, she became the first Best Actress winner to wear Givenchy since Audrey Hepburn, though Hepburn’s dress is still up for debate.

Some stars take risks, some go classic, but Stone’s choice was the perfect balance of both. Elegant, dazzling, and just theatrical enough, it felt like a fitting tribute to the golden age of musicals, and the golden trophy she took home that night.

15. Billy Porter tuexedo dress at the 2019 Oscars

Billy Porter didn’t just attend the 2019 Oscars, he owned them. Ditching tradition, he walked the red carpet in a jaw-dropping Christian Siriano tuxedo gown, proving that fashion has no rules. The top half was a sharp, classic tux, while the bottom billowed into a full, dramatic black velvet skirt. The result? Pure red carpet royalty.

This wasn’t just about looking fabulous (though he absolutely did). It was a statement, bold, fearless, and unapologetically glamorous. Porter redefined menswear in Hollywood with one unforgettable look, reminding everyone that Oscar fashion isn’t just for the women. Some outfits turn heads. This one changed the game.

14. Natalie Portman’s stunning Dior gown at the 2020 Oscars

Natalie Portman’s 2020 Oscars look wasn’t just fashion, it was a message. Wearing a stunning Dior gown with a sheer black overlay, she topped it off with a dramatic cape embroidered with the names of female directors who had been snubbed in the Best Director category. Among them? Greta Gerwig, Lorene Scafaria, Mati Diop, and Lulu Wang, talented filmmakers who deserved a spot but didn’t get one.

In a sea of glitz and glamour, Portman’s look stood out not just for its elegance but for its purpose. It was subtle yet powerful, a stylish reminder that Hollywood still has work to do when it comes to recognizing female talent behind the camera. Fashion statements at the Oscars usually come in sequins and trains, but Portman proved that embroidery can speak just as loudly.

13. Lily Gladstone makes a statement at the 2024 Oscars

Lily Gladstone’s 2024 Oscars look wasn’t just about fashion, it was about representation. As the first Native American woman nominated for Best Actress, she walked the red carpet in a breathtaking deep blue Gucci gown, created in collaboration with Indigenous designers Joe and Sunshine Big Mountain. The gown blended high fashion with cultural significance, a perfect reflection of Gladstone’s commitment to uplifting Native voices.

Her choice wasn’t just about looking stunning (though she absolutely did). It was a statement of pride, history, and artistry. And she didn’t stop there, at the Vanity Fair Oscar Party, she changed into a beaded ensemble by the same designers, further honoring Indigenous craftsmanship on one of Hollywood’s biggest nights.

Some dresses dazzle; others tell a story. Gladstone’s did both, making her Oscars moment not just stylish but deeply meaningful.

12. Emma Stone prove why she is a red-carpet favourite once again at the 2024 Oscars

Emma Stone’s 2024 Oscars look was pure red-carpet royalty. Dressed in a custom Louis Vuitton gown in a dreamy mint hue, she brought a fresh, modern twist to Old Hollywood glamour. The strapless silhouette, complete with an architectural peplum skirt, made a bold yet effortlessly elegant statement.

And let’s talk about that bling. Stone’s stylist, Petra Flannery, paired the gown with a jaw-dropping 30-carat yellow diamond necklace from Louis Vuitton’s High Jewelry collection because if you’re going to the Oscars, why not sparkle like a literal star?

Even her hair was a masterpiece, with stylist Mara Roszak drawing inspiration from the dress’s “classic architecture” to create a sleek, polished look. The result? A perfectly balanced combination of vintage charm and modern sophistication.

From head to toe, Stone once again proved why she’s a red-carpet favorite, always taking risks, always looking stunning, and always leaving us wanting more.

11. Colman Domingo’s look at 2024 Oscars

Colman Domingo knows how to make a statement, and his 2024 Oscars look was no exception. The Rustin star, nominated for Best Actor, arrived in a sleek tuxedo with silver buttons, proving that classic black tie doesn’t have to be boring. But the real showstoppers? His accessories.

Domingo elevated his ensemble with eight pieces of David Yurman jewelry, plus one deeply meaningful addition, a pinky ring that once belonged to Bayard Rustin himself. Talk about a full-circle moment! And let’s not forget the cowboy boots with silver-toe detailing, adding just the right amount of edge.

From his bold fashion choices to the subtle nods to his film’s legacy, Domingo once again showed that style isn’t just about looking good, it’s about telling a story.

10. Rita Moreno spreads her magic at the 2024 Oscars

Rita Moreno proves time and time again that style has no age limit. At 92, she’s still owning the red carpet like a queen. For the Oscars, the legendary actress, who was on presenting duty, teased that her look would be a showstopper. And she wasn’t kidding. She arrived in a 3D black Badgley Mischka hourglass gown with cascading ruffles, turning heads like only she can.

And because drama is her signature, she added opera gloves (because why not?) and styled them with a gold timepiece, because even elegance needs a little edge. With a high neckline, a mini train, and a presence that commands attention, Moreno once again proved she’s an icon in every sense of the word.

As she joked on Today before the big night,

I’m going to wear a gown that’s gonna knock your socks off.

Safe to say, she did just that.

9. Michelle Yeoh’s Balenciaga gown at the 2024 Oscars

Michelle Yeoh is the definition of red carpet royalty, and she proved it once again at the 96th Academy Awards. The Oscar-winning actress and presenter dazzled in a custom Balenciaga sequined gown, a shimmering one-shoulder masterpiece that exuded timeless elegance. Yeoh paired the silver dress with black opera gloves and matching pumps, striking the perfect balance between classic Hollywood glamour and modern sophistication.

For accessories, she didn’t hold back on the sparkle. She completed her look with Diamond Foliage Earrings by jewelry artist Cindy Chao and a sleek, elegant watch that stood out against her gloves. Her sleek updo and natural, glowy makeup added to the refined allure. Yeoh has mastered the art of award-show fashion, hands down.

8. Charlize Theron doesn’t miss at the 2024 Oscars

Charlize Theron never misses when it comes to red carpet glamour, and the 2024 Oscars were no exception. The Academy Award winner arrived in a stunning Dior Haute Couture gown, a pale silver masterpiece with elegant draping at the shoulder and a delicate twist detail at the bust. The flowing silhouette pooled gracefully at her ankles, exuding sophistication and timeless style.

Theron’s accessories were just as dazzling. She layered on Boucheron jewels, including rings, bracelets, chokers, and earrings, adding the perfect amount of sparkle to her refined look. Keeping the focus on her striking features, she opted for a slicked-back hairstyle and soft, rosy makeup with a natural lip and flushed cheeks.

Beyond turning heads on the red carpet, Theron took on another important role during the night, presenting on the Oscars stage. With her signature confidence and impeccable style, she proved once again why she’s a Hollywood fashion icon.

7. Ariana Grande’s red carpet return at the 2024 Oscars

Ariana Grande’s red carpet return was nothing short of magical. The 30-year-old pop sensation made a stunning entrance at the 2024 Oscars, where she presented an award alongside her Wicked co-star Cynthia Erivo. Dressed in a custom Giambattista Valli Haute Couture gown, Grande embraced full Glinda energy in a blush pink strapless ruched column dress, complete with an exaggerated off-the-shoulder puff sleeve cape and a flowing train.

To complete the dreamy ensemble, she accessorized with pink-stone drop earrings and a delicate pendant necklace, adding just the right touch of sparkle. Her sleek, pulled-back updo kept the focus on the gown’s ethereal design.

Grande’s return to the red carpet comes four years after her last major appearance at the 2020 Grammys, where she turned heads in a voluminous Giambattista Valli ballgown that took 400 yards of tulle and 200 hours to construct.

6. Florence Pugh makes a statement at the 2024 Oscars

Florence Pugh knows how to make a statement, and her 2024 Oscars look was no exception. She arrived in a stunning silver Del Core gown, featuring a sculpted sheer bodice with delicate beading designed to resemble water droplets on a leaf. The plunging neckline, flowing fabric, and short train made the dress both ethereal and bold.

Styled by Rebecca Corbin Murray, Pugh accessorized with Bulgari jewels and Piferi platform heels, while hairstylist Adir Abergel took inspiration from Madonna’s 1990s era, crafting a modern-day bombshell hairstyle. According to Abergel, the effortless, swept-to-the-side look was meant to celebrate Oppenheimer’s 13 Oscar nominations.

Pugh joined her fellow “Oppenhomies” at the ceremony, where the film was nominated for Best Picture, Best Director, Best Actor, Best Supporting Actor, and Best Supporting Actress. With Oppenheimer dominating the awards season, her red carpet presence was just another winning moment.

5. Elizabeth Olsen’s black gown at the 2023 Oscars

Elizabeth Olsen brought effortless edge to the 2023 Oscars in a slinky black Givenchy gown that redefined red carpet glamour. The chain-mail-inspired dress shimmered under the lights, proving that black is never boring, especially when done with this much drama and sophistication.

Keeping her look minimal yet striking, Olsen let the dress do all the talking, opting for simple accessories and sleek styling. The ensemble was a perfect blend of old Hollywood elegance and modern-day boldness, making her one of the evening’s best-dressed stars.

If there was ever proof that a classic black gown can still turn heads, Elizabeth Olsen just delivered it in the most stunning way possible.

4. Zoë Kravitz doesn’t miss at the 2022 Oscars

Zoë Kravitz served modern Audrey Hepburn realness at the 2022 Oscars in a pale pink Saint Laurent gown that oozed elegance. The sleek, strapless design hugged her frame perfectly, proving that sometimes, simplicity steals the show.

She completed the look with a classic diamond necklace, adding just the right amount of sparkle. But the real standout? Those chic baby bangs, giving the entire ensemble a retro yet refreshingly modern twist.

With her signature effortless cool, Kravitz turned a timeless Hollywood aesthetic into something uniquely hers, graceful, refined, and undeniably iconic.

3. Zendaya goes yellow at the 2021 Oscars

Zendaya knows how to own the red carpet, and the 2021 Academy Awards were no exception. Dressed in a breathtaking sunshine yellow Valentino gown, she radiated effortless glamour. The strapless design featured a flowing silhouette with a subtle midriff cutout, adding a touch of modernity to the classic elegance. It was bold yet sophisticated, exactly what we expect from Zendaya’s red-carpet reign.

She let the dress do most of the talking but didn’t hold back on the accessories. Stacked Bulgari diamonds added just the right amount of sparkle, complementing her flowing, waist-length waves and glowing, sun-kissed makeup. The entire look felt fresh, breezy, and perfectly suited for an actress who consistently pushes the fashion envelope.

Zendaya’s 2021 Oscars look wasn’t just a fashion moment; it was a red carpet masterclass. Whether she’s channeling Old Hollywood or stepping out in cutting-edge couture, she always delivers. This Valentino moment was bright, bold, and completely unforgettable, another win in her already iconic style evolution.

2. Amanda Seyfried’s red gown at the 2021 Oscars

Amanda Seyfried made sure all eyes were on her at the 2021 Academy Awards in a breathtaking red tulle ball gown by Armani Privé. The voluminous dress featured a plunging neckline and a structured bodice, creating a striking silhouette that felt both classic and daring. The rich crimson hue gave off major Old Hollywood vibes, a fitting choice for the actress, who was nominated for her role in Mank, a film about the golden age of cinema.

Keeping her accessories minimal, Seyfried let the gown take center stage, pairing it with statement earrings and a sleek updo that emphasized the gown’s dramatic neckline. Her makeup was equally timeless, featuring a bold red lip that perfectly matched the dress.

From the delicate tulle layers to the impeccable fit, this look was pure Oscars-worthy glamour. Seyfried’s Armani Privé moment wasn’t just a dress, it was a fashion statement, proving that sometimes, going all out is the best choice.

1. Rihanna proves why she is the red carpet icon at the 2023 Oscars

Rihanna made a statement at the 95th Academy Awards on March 12, 2023, proving once again why she’s a red carpet icon. She arrived in a sheer latex halter top with an elongated train from Alaïa, effortlessly blending edginess with elegance. But in true Rihanna fashion, one show-stopping look wasn’t enough.

Before hitting the stage to perform her Oscar-nominated song Lift Me Up from Black Panther: Wakanda Forever, she swapped the sultry latex for a glittering Maison Margiela number. The shimmering gown captured the perfect mix of drama and sophistication, ensuring all eyes were on her as she delivered a breathtaking performance.

Rihanna’s maternity style has been nothing short of groundbreaking, and this Oscars moment was no exception. She continues to redefine fashion on her own terms, proving that pregnancy doesn’t mean compromising on bold, fashion-forward looks. Whether in Alaïa or Maison Margiela, one thing is certain, Rihanna knows how to own the spotlight.

 

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