Octavia Spencer

All in all, 2012 was a great year for red carpet fashion! At the Oscars, Octavia Spencer rocked this sparkly ivory dress by Japanese designer Tadashi Shoji as she accepted the award for Best Actress in a Supporting Role for her part in The Help.

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The silky, hand-beaded gown reportedly took over 1,000 hours of work by a team of 10 people to perfect for its red carpet debut. All the effort was worth it, however, as Spencer dominated the runway, looking confident, beautiful, and poised in the super-flattering ensemble.    

Michelle Williams

Although Michelle Williams didn’t take home the prize for Best Actress in a Supporting Role at the 2006 Oscars, the Brokeback Mountain ingenue easily won over the red carpet with this sunny yellow look. 

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The Vera Wang gown, with its pleats and knotted details, paired perfectly with Williams’ slightly messy updo and classic red lip. The vintage-inspired dress is both modern and timeless and remains an iconic Oscars fashion moment more than 10 years later. 

Hilary Swank

Sometimes a simple, streamlined look can have the biggest impact. This is certainly the case for Hilary Swank’s 2005 Academy Awards ensemble, featuring a gorgeous navy-blue dress designed by Guy Laroche. From the front, the floor-length silk dress didn’t seem all that groundbreaking, though the high neck and crisscrossed panels did look positively sublime on the Million Dollar Baby star.

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The real “wow” factor came when Swank turned her back to the cameras, unveiling an absolutely stunning backless cut that showed off the star’s toned figure and flawless skin. The polished, elegant look was incredibly well received by critics, with several publications including it among the best Oscar dresses of all time.  

Lupita Nyong’o

In 2014, Lupita Nyong’o was one of the hottest rising stars in the world, having just snagged the award for Best Actress in a Supporting Role for her first major film role, in 12 Years a Slave.

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For her big win, Lupita wore an ethereal pastel-blue dress by Prada, which the actress stated was inspired by “champagne bubbles.” The effortlessly elegant look perfectly suited the Kenyan-Mexican actress, who wore her hair in a close-cropped natural style with a delicate silvery headband, and paired it with minimal accessories to let the flowy gown take center stage. 

Meryl Streep

Meryl Streep turned heads as she walked the 2012 Oscars red carpet, smiling and waving for the crowds and looking stunning at 63 years old. The veteran actress won the award for Best Actress that year for her role as Margaret Thatcher in the historical biopic The Iron Lady, though one could argue that she looked more like a “golden lady” in this stunning draped gold lamé number by Lanvin.

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Streep’s look exuded pure glamour, complete with glistening gold accessories and a mother-of-pearl-encrusted clutch. Though she had been a household name for some time by this point in her career, fashion critics swooned over the look and many claimed that this is the best she’s ever looked! Do you agree? 

Kate Hudson

Kate Hudson, who was almost guaranteed success in the entertainment industry due to her impressive pedigree (her mother is Goldie Hawn and her father figure growing up was Kurt Russell), clearly inherited her famous mom’s good looks as well as her acting chops.

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For her 2003 Oscars appearance, Hudson wore an alluring lace Versace gown in pale yellow, paired with a softly tousled hairstyle that conveyed femininity and grace. The romantic look, which had an almost bridal feel due to the delicate beading and gauzy train, has continued to be hailed as one of the best Oscars ensembles to this day.    

Jane Fonda

Fitness and fashion model-turned-actress Jane Fonda made jaws drop with this clean, modern, all-white look at the 2018 Academy Awards.

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The 80-year-old (yes, you read that right) looked positively stunning in the sparkle-encrusted Balmain sheath dress, showcasing her incredible figure and the voluminous blonde bob she has come to be known for. The structured, modern look perfectly suited the star, and a minimal makeup look kept the focus where it belonged — on Ms. Fonda herself. 

Charlize Theron

In 2015, South African actress Charlize Theron amazed the crowd at the Cannes film festival in this striking yellow Dior frock that fit her like a gorgeous glove. The Mad Max: Fury Road star is known to bring her A-game when it comes to fashion, often topping best-dressed lists and sporting big-name designers like Gucci, Dior, and Lanvin.

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Theron looks sensational in the fitted gown, paired with a sleek, classic updo and glittering diamond statement earrings by Chopard. The long, sweeping train takes the glamour level over the top, cementing this as one of her best looks of all time! 

Katy Perry

The Met Gala red carpet is a treasure trove of unique looks each year, and 2019’s was no different — the “Camp” theme yielded some crazy celebrity getups that will certainly go down in fashion history.

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Notably, singer Katy Perry took the theme to its logical conclusion by showing up in a bedazzled cheeseburger costume, complete with matching burger shoes and a toothpick hat. The look, designed for Perry by Jeremy Scott, made waves both at the gala and on social media, as its general ridiculousness made for excellent meme material. 

Gwen Stefani

Ah, the glorious ’90s. Some say it was a dark age for fashion, rife with tacky sartorial trends we’d rather forget, like sky-high platform shoes, jelly bracelets, and the perpetually unflattering “skirt over pants” silhouette. For the 1998 VMAs, Gwen Stefani, then the leading lady of No Doubt, managed to incorporate all these elements (and more) into an outfit that’s so appallingly ’90s, it almost comes full circle into being cool again.

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The furry bra, the blue space-bun hair, and the stick-on crystals combined with a shiny black pool-noodle-looking skirt and chunky platform flip-flops have become so representative of the era that the look has inspired hundreds of DIY Halloween costumes in recent years. Let’s just hope it stays firmly confined to costume parties, because we just can’t handle JNCO jeans and bucket hats making a comeback.  

Celine Dion

OK, OK … so it’s not technically a dress, but this look has become so well known that it seems almost impossible not to include in this list of memorable red carpet looks. The Canadian songstress took an avant-garde approach to the popular menswear trend and turned it upside down (or backward, more accurately), shocking onlookers at the 1999 Oscars.

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The John Galliano-designed ensemble was almost universally panned at the time, but has since become one of the most notable outfits in all of Oscars history. It just goes to show how sometimes taking a fashion risk can pay off majorly!     

Lady Gaga

Enigmatic performer Lady Gaga is known for making powerful statements with her artistic and fashion choices, but perhaps no stunt caused more controversy than her 2010 VMAs outfit — a one-of-a-kind dress with matching shoes made from actual raw beef. The so-called “meat dress,” designed by Franc Fernandez, shocked audiences, who immediately started analyzing the singer’s fashion choice to discern what type of statement she was making.

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Theories ranged from anti-fashion, feminism, and funnily enough, both pro- and anti-veganism. Gaga later addressed this speculation on The Ellen DeGeneres Show, saying, “For me this evening, if we don’t stand up for what we believe in and if we don’t fight for our rights pretty soon, we’re going to have as much rights as the meat on our own bones. And, I am not a piece of meat.”

Jennifer Lawrence

Back in 2013, Jennifer Lawrence was the newest “it girl” to watch, her popularity rocketing largely due to the huge success of blockbusters like Hunger Games,  X-Men: First Class, and Silver Linings Playbookthe latter of which earned her the Best Actress award that year — making her the second-youngest actress ever to win that category.

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It goes without saying that she was anticipated to make a huge impact on the red carpet, which she did in more ways than one. She captivated the crowd as she entered in a pale-pink Dior Couture ball gown featuring a full, flowing skirt that, while elegant, proved to be quite difficult to manage, as the 22-year-old star tripped noticeably over the hem on her way to the stage to accept her Oscar. Not to worry — she recovered gracefully and went home a winner!

Cher

If there’s one way to ensure that absolutely everyone will be talking about your outfit on the red carpet, it’s hiring longtime Hollywood designer Bob Mackie as your stylist. That’s exactly what Cher did for the 1986 Academy Awards, and the result was spectacular, to say the least.

Don Ameche and Cher at Academy Awards/Getty Images

The two-piece garment, covered in hundreds of sparkly sequins in decorative geometric patterns, showcased Cher’s killer bod as she walked the red carpet. The outfit was topped off with a dramatic 2-foot-tall feathered headdress reminiscent of a Vegas showgirl costume. Though she wasn’t even nominated that year, Cher certainly made sure that the spotlight was firmly fixated on her all night long. 

Björk

Of all the legendary celebrity looks on this list, this dress may be the most infamous. Way before stars were walking the red carpet dressed as hamburgers or butcher-shop windows, Björk donned this Marjan Pejoski creation, which engulfed the Icelandic singer in a large, feathery swan.

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To add to the bizarre effect, she then proceeded to “lay” 6 huge ostrich eggs in the middle of the red carpet. Even though almost everyone openly hated the dress, it was so outlandish and memorable that it became the subject of countless jokes and parodies, firmly securing its place in fashion history. 

Beyoncé

Beyoncé has rocked countless unforgettable looks throughout her career as a singer/actress/queen of the world, but this barely-there gown from the 2015 Met Gala may be one of her most recognizable.

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The superstar actually showed up late to the event and was almost written off as a no-show when she suddenly appeared in a jewel-encrusted, transparent Givenchy stunner. Unsurprisingly, heads turned, cameras flashed, and Queen Bey made headlines yet again. Some argue that another star outshone her, however … 

Rihanna

While Beyonce’s sparkly see-through number certainly garnered quite a bit of attention, Rihanna may have stolen the spotlight in 2015 with her jaw-droppingly dramatic Guo Pei dress.

Rihanna met gala 2018 dress
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The huge golden cape-style gown was trimmed with thick, fluffy fur and embroidered with gorgeous floral motifs, and the sweeping train was so long that the Barbadian singer and fashion designer couldn’t walk without assistance. Regardless of its impracticality, the dress certainly fit the event’s Chinese theme perfectly, and kept people talking about it for weeks to follow. Whether RiRi or Queen Bey ultimately won the night, you’ll have to decide for yourself.     

Audrey Hepburn

The red carpet of the Academy Awards has been graced by countless stars throughout the event’s 90+ years in existence, ranging from big names to up-and-comers. Among them is one of history’s greatest fashion icons, the incomparable Audrey Hepburn.

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Hepburn, who would win the Best Actress award that year for Roman Holiday, attended the 26th annual Academy Awards dressed in a tailored Givenchy frock with a belted waist that perfectly complemented the actress’s petite frame. The floral, feminine dress in ivory lace soon became one of Audrey’s favorites — she even called it her “lucky dress.” The dress’s luck doesn’t seem to have run out yet, as it was listed for auction in 2011 with a suggested price of $64,000 to $96,000!      

Cindy Crawford

At the height of her career, supermodel Cindy Crawford’s name was synonymous with glamour and elegance. She appeared on countless magazine covers, high-fashion runways, and red carpets, and was often referred to as “the most beautiful woman in the world.”

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One particular fashion moment, featuring a skin-tight red Versace dress with a plunging neckline she donned for the 1991 Oscars, may have been the most impactful of all. The slinky sheath gown rocked the fashion world, inspiring countless copies and imitations, and it’s not hard to see why; the ravishing beauty looks flawless as she walks the red carpet with her boyfriend at the time, actor Richard Gere.     

Jennifer Lopez

All of the looks on this list are iconic in their own way, but how many can say they revolutionized the entire internet? When Jennifer Lopez showed up to the 2000 Grammys, her racy green Versace dress caused such a commotion online that Google was inspired to develop its image search feature to keep up with the public’s demand for photos of the controversial outfit.

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The flowy leaf-printed dress featured a neckline that plunged so low it bared her belly button, and was considered by many at the time to be “too revealing” — but despite criticism, it became one of the most well-known celebrity looks of all time. Twenty years later, JLo broke the internet once again by wearing an updated version of the legendary dress down the Milan Fashion Week runway, and somehow managed to look even better at 50 years old! 

Sharon Stone

Some stars try to stand out on the red carpet by going completely over the top with glamorous details and crazy accouterments, and others, like the alluring Sharon Stone, choose to rely on a more “Basic Instinct” when selecting an award-show look.

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Eschewing the traditional ball-gown aesthetic, Stone opted instead for a silky lavender Vera Wang skirt and a white button-up collared shirt from the Gap for the 1998 Oscars. The look took audiences by surprise with its unique approach, combining casual and formal with feminine and masculine elements.

Julia Roberts

Another early adopter of the menswear trend in the high-end fashion scene was a young Julia Roberts, who sported an oversize men’s Giorgio Armani suit at the 1990 Golden Globe Awards. The actress, who accessorized the suit with a purple patterned necktie and her gorgeous curls flowing loosely over her shoulders, accepted the award that evening for Best Actress in a Supporting Role in Steel Magnolias.

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She would go on to repeat the tradition the following year, when she wore a pinstriped tuxedo-inspired dress and took home the award for Best Performance by an Actress for her starring role in Pretty Woman. Roberts must be a die-hard fan of the style, as she’s regularly spotted in blazers and tuxedo pants on the red carpet to this day. 

Barbra Streisand

It’s hard to imagine entertainment powerhouse, Barbara Streisand, as a newcomer to the scene, but even the greatest stars had to start somewhere. Back in 1969, she was a rookie performer who had been invited to her very first Oscars as a nominee for Best Actress.

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The Funny Face star selected an atypical look for her red carpet debut, donning a sequined pantsuit with a Peter Pan collar and oversize bow that, much to Streisand’s surprise, became entirely transparent under the bright stage lights. Despite the embarrassing realization, she still went home with the trophy and went on to become one of the most recognizable stars of all time, so … it could be worse.   

Rita Moreno

Rita Moreno, one of the few artists throughout history to be considered an EGOT (that is, having won an Emmy, a Grammy, an Oscar, and a Tony), surprised everyone at the 2018 Oscars by wearing the same exact dress she wore back in 1962, when she accepted the Oscar for Best Actress in a Supporting Role for her role as Anita in West Side Story.

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The vintage black-and-gold frock, which was designed in the Philippines, got a slight face-lift for the event, converting it into a strapless dress, but it still retained the classic elegance of the original. Moreno paired the Asian-inspired gown with gold accessories and a black headband this time, but also chose to wear the same black evening gloves, looking just as stunning as her younger self, if not more so!        

Madonna

“Material Girl” Madonna has sported so many memorable looks throughout her illustrious career, it’s almost impossible to choose just one! With that being said, there’s just so much to talk about with Madge’s 1991 Oscars dress.

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First of all, the Queen of Pop channeled another megastar: Her curly blonde locks, bold red lip, and Old Hollywood-style bejeweled Bob Mackie gown echoed Marilyn Monroe’s classic look. Then, there’s the fact that she rocked (no pun intended) about $20 million worth of diamond jewelry. If that wasn’t enough, Madonna’s date — an up-and-coming young musician who looks strangely familiar for some reason — caused a stir as well.      

Farrah Fawcett

The original blonde bombshell, Farrah Fawcett has always embodied the laid-back coolness of the ’70s with her fashion choices. Often seen sporting disco-ready styles like bell-bottoms and loose, flowy dresses along with her signature cascading curls, the Charlie’s Angels actress inspired thousands of young women to copy her signature look.

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Pictured here at the 1989 premiere for Chances Are with husband Ryan O’Neal, Fawcett stuns in a curve-hugging, metallic accented dress that sparkles so brightly, no additional accessories were needed. As always, the star is rocking her famous golden locks, which perfectly complement her shiny gown for a look that radiates a bold yet easygoing style.  

Elizabeth Hurley

Versace makes the list again with this slinky black number worn by British actress and model Elizabeth Hurley to the Four Weddings and a Funeral premiere in 1994. Hurley, who was dating actor Hugh Grant at the time, says she chose the now-famous dress not because it was especially important to her, but because it was the last available choice.

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The punk-inspired gown ended up making waves for its edgy details and daring cut, with some detractors saying that it was too scandalous. Little did they know the look would become so well known that it would be referred to simply as “that dress,” and would be credited with launching both Hurley and the fashion house of Versace into superstardom territory.    

Angelina Jolie

Angelina Jolie has certainly had her fair share of moments in the spotlight, but perhaps the most well known (and definitely the most parodied) is the time when, while modeling for photographers outside the 84th Academy Awards, the actress struck a bold pose with her hand on her hip and a long slit in her black velvet Versace gown revealing her dramatically extended right leg.

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The pose immediately took off as a trending topic on social media, starting with her leg getting its own Twitter account (@AngiesRightLeg), and continued by being endlessly lampooned for weeks afterward with Photoshopped images, look-alike parodies, and hashtags like #angellegging, #joliening, and #legbombing.   

Kacey Musgraves

The singer-songwriter took the 2019 Met Gala’s “Camp” theme to the extreme, showing up dressed as everyone’s favorite plastic blonde bombshell, Barbie. The playful star showed up in a head-to-toe hot-pink Barbie fantasy outfit, complete with a hairdryer purse, cat-eye sunglasses, and a giant fluffy fur stole.

Photo by Dia Dipasupil/FilmMagic

She even went the extra mile by arriving at the pink carpet with a Barbie flourish, waving from the back of a matching pink “Dream Car” convertible. Needless to say, spectators loved the theatricality of the outfit, which was designed by Jeremy Scott for Moschino, and the Twitterverse immediately exploded with photos of the look and praise for their creative interpretation of the night’s theme. 

Grace Kelly

The aptly named Grace Kelly was known for her poise and refined, stately style, so it’s no surprise that the future Princess consort of Monaco is still getting praise for her regal ensemble at the 1956 Academy Awards.

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Looking every inch a princess, Grace wore a feminine floor-length gown with floral details covered with a chic satin wrap, and accessorized with white wrist gloves and a sleek, ballerina-like bun. Shortly after this appearance, she would jet off to Monaco for her marriage to Prince Rainier III, where her attire would make history once again — her lacy, long-sleeved wedding dress inspired bridal fashion for years to come, including fellow royal Kate Middleton. 

Zoe Saldana

Before Zoe Saldana joined the Marvel Universe as the green guardian Gamora, she was enjoying the fame that followed her major roles in huge releases like Avatar and the 2009 Star Trek reboot.

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The rising star dominated the 2010 Oscars red carpet in a lavender ombré Givenchy gown adorned with crystals and ruffles galore. The sculptural gown, which looked amazing on the young starlet, stood out from the regular crowd in the best way due to its vivid colors and three-dimensional details.   

Lauren Hutton

If ever a look truly encapsulated the era it was designed in, model/actress Lauren Hutton’s dreamy Halston dress from the 1975 Oscars would have to be among the top contenders.

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The flowy, pleated gown with pastel rainbow colors, topped off with a luxurious fox fur coat, exuded pure ’70s glam, and Hutton’s easy, natural makeup and minimal accessories made for a laid-back yet captivating style that would be emulated by others for years to come.