The Most Iconic Oscars Dresses From The Last 20 Years

Ahh, the Oscars are upon us. Otherwise known as the Academy Awards (or the pop culture fanatic's Superbowl), Oscars night is an evening known for showcasing the glitz and glam of Hollywood in all its fame and glory. The first-ever Academy Awards ceremony took place on May 16, 1929, saw under 300 guests, and wasn't broadcast to the public. In fact, according to The Telegraph, the name "Oscar" was not yet in use. 


The Academy Awards have certainly evolved since their inaugural ceremony nearly a century ago — for example, the average number of viewers of the 2016 Academy Awards was a mere 34.4 million. However, one constant has remained throughout the years — those glamorous Oscars gowns. 

We're guessing you've likely never made it to the Academy Awards. However, you can live vicariously through the 20 most iconic Oscars dresses from years past. From Gwyneth Paltrow's pretty-in-pink moment to the infamous swan dress, this trip down Oscars lane has all the hits. 

1998: Madonna channels her inner goth girl

The 70th Academy Awards ceremony took place on March 23, 1998, a month after the release of Madonna's seventh studio album — Ray of Light. It had been an exciting time for the superstar songstress — just a year prior, the multi-talented Madonna was making the rounds at awards ceremonies for her starring role in Evita. However, though her performance won her the Golden Globe for Best Actress in 1997, she was not nominated for an Academy Award. The snub came as a shock to many, but Madonna didn't have time to wallow in self-pity. Instead, she threw herself wholeheartedly into working on Ray of Light, an electronica/dance album that was a definite departure from her previous albums. According to Rolling Stone magazine, "[Ray of Light] was her spiritual-awakening statement." 


Madonna has never been one to shy away from making a statement with her work, her words, or her wardrobe. So it was no surprise when the iconic pop star and actress arrived at the 70th Academy Awards wearing dramatic and sultry satin coat-dress from the (then) largely unknown Belgian designer, Olivier Theyskens. She looked like a total gothic fairy princess as she seemingly floated onstage to present the award for Best Original Song to Celine Dion for "My Heart Will Go On." Of course, she couldn't help but to make a friendly jab at the Canadian singer. Once a statement maker, always a statement maker. 

1999: Gwyneth Paltrow is pretty in pink

Perhaps the most talked about Academy Awards moment belongs to Gwyneth Paltrow, both for her iconic pink gown and her highly-criticized acceptance speech. Paltrow was nominated for the Best Actress award for her performance in 1998's romantic comedy/drama, Shakespeare in Love – an award that she would go on to win with a simultaneously tearful and tearless acceptance speech. According to Paper magazine, Paltrow's confusing monologue while accepting her award was the downfall of sincerity within acceptance speeches. It's an Academy Awards moment that solidified its place within countless blogs and listicles — just as her bubblegum-pink gown remains one of the most talked about Oscars dresses to this day. 


Paltrow looked as if she'd just stepped out of a fairytale book as she smiled and posed for red carpet photographers. The ballgown was quite simple in design — featuring spaghetti straps, a sweetheart neckline, and a floor-length skirt — but Paltrow made it her own. In 2015, the star revealed to People that she "stockpiles" her favorite gowns in hopes that Apple, her daughter, might someday find a use for them. Who needs millennial pink when pre-millennium pink looks this good? 

2000: Tyra Banks is red carpet royalty

Of course every celebrity hopes to be named among the best-dressed on the red carpet at the Academy Awards. Unfortunately, the media can be a tough, unforgiving (and un-forgetting) crowd. The pressure to choose the right dress, the perfect color, and the best designer can feel insurmountable — one wrong move, and a star will find themselves on "worst dressed" and "fashion don'ts" listicles for countless awards seasons to come. Unlike your embarrassing prom photo that your parents refuse to take off the living room wall, what happens on the red carpet stays forever in the hearts and minds of pop culture aficionados everywhere. You just thought you had it bad. 


On a positive note, any media is good media — right? You'll have to ask bonafide superstar Tyra Banks, who quickly found herself on the worst dressed lists from the 72nd Academy Awards ceremony. While she walked the red carpet with a confidence only Banks can channel (with her signature smize, as always), the lavender ensemble with the poof of a skirt from designer Vera Wang was a major miss in nearly everyone's book. Entertainment Weekly graded the gown a 'D,' calling it "the night's biggest dud." While it might not have been a winner, it was most certainly iconic — and Banks has definitely redeemed herself time and time again. 

2001: Björk serves major Swan Princess vibes

It's unusual for a red carpet dress to make such an impact on American pop culture that it is subsequently honored in a national museum. Then again, Björk is far from your usual celebrity. The Icelandic songstress was nominated at the 73rd Academy Awards for her song, "I've Seen It All." The haunting tune was featured in the Lars von Trier film, Dancer in the Dark, which also starred Björk in the leading role. Though she didn't win the Oscar for Best Original Song, the eclectic singer-songwriter delivered a performance of the song that was as powerful as it was peculiar. And, oh — she did it while wearing a swan. 


It was a dress unlike anything the red carpet had ever seen — quite fitting for a performer unlike any other. However unique the dress was, the most memorable part of Björk's red carpet appearance happened when the singer lifted her feathered skirt and laid an egg. Even the designer of the infamous swan dress, Marjan Pejoski, couldn't believe what happened. However, he didn't seem to be bothered. In an interview with Vogue, Pejoski said, "It was fantastic of her. So rebellious, at a traditional occasion like the Oscars. I respect tradition of course, but everybody and everything deserves to be laughed at from time to time."

2002: Halle Berry is sheer, sexy, and shocked

Halle Berry is one of the most memorable celebrities to walk the red carpet, but the actress' unforgettable dress at the 74th Academy Awards wasn't the only thing to make history that night. Berry won the Academy Award for Best Actress for her remarkable performance in Marc Forster's Monster's Ball. By receiving the coveted golden statue, Berry became the first black woman ever to win the lead actress Oscar. 


It was truly a significant moment in Oscars history, for which Berry delivered a powerful, chill-bump-inducing acceptance speech. "This moment is so much bigger than me," she said through tears. "[It's] for every nameless, faceless woman of color that now has a chance because this door tonight has been opened." 

An iconic Oscars moment deserves an iconic Oscars dress, and Berry delivered both. The actress donned a figure-hugging, netted Ellie Saab number in a deep maroon hue with a silk, sheath skirt and delicate floral embroidery. It was certainly a perfectly unforgettable dress for a perfectly unforgettable moment. 

2003: Jennifer Lopez glows in mint green

Though she's a talented actress, Jennifer Lopez has never been nominated for an Academy Award — but her iconic style has always been welcome on the red carpet. Honestly, who can forget that stunning, plunging, green Versace dress the singer wore to the 42nd Grammy Awards in 2000? This gal knows how to work a carpet and a camera. 


Green is obviously the superstar's color, as evidenced by the mint green Valentino gown she wore to the Academy Awards in 2003. Lopez served major classic Hollywood vibes as she walked the red carpet with then-beau Ben Affleck. One could even say that Lopez closely resembled a certain fashionable First Lady. According to the Valentino Garavani museum, the one-shoulder number donned by Lopez on the red carpet was inspired by a similar one-shoulder gown worn by Jackie Kennedy Onassis during a 1967 visit to Cambodia. 

2004: Charlize Theron looks like a living gold statue

Charlize Theron might be known for her drop-dead gorgeous looks, but the actress proved that she's so much more than a pretty face with her jaw-dropping performance in 2004's Monster. The movie, based on the life of notorious serial killer Aileen Wuornos, saw Theron make the incredible transformation from classic Hollywood beauty to a tormented and terrifying serial killer. The star is nearly unrecognizable in the film, the credit of which is due to both a talented team of makeup artists and Theron's own spectacular acting chops. The performance earned Theron the Best Actress Oscar at the 76th Academy Awards — the first nomination and win for the actress. 


Theron looked like a golden statue herself as she accepted the award. Her shimmering, silver Gucci gown hugged all the right curves and showcased the Hollywood starlet's sun-kissed skin, leading one to imagine just how much work went into transforming this gorgeous, golden goddess into the titular monster. 

2005: Sandra Oh, lady in red

Sandra Oh is best known for her performance as Dr. Cristina Yang on ABC's hit medical drama, Grey's Anatomy. However, only a year before the first episode of Grey's Anatomy made its way into the homes and hearts of Americans everywhere, Oh was strutting her stuff on the red carpet at the 76th Academy Awards. The talented actress stunned in a sexy Michael Kors gown that was certainly a far-cry from the hospital scrubs with which Oh would soon become synonymous. 


Oh received much praise from critics for her performance in the 2004 black comedy, Sideways. Though she didn't receive an Academy Award nomination for her performance, Oh absolutely stole the show in this red-hot number reminiscent of old Hollywood. The Michael Kors creation featured a figure-flattering mermaid silhouette and a strapless, sweetheart neckline — which was beautifully highlighted by Oh's choice of a delicate filagree, diamond, and pearl necklace. 

2006: Reese Witherspoon is a real-life Cinderella

Reese Witherspoon stole hearts with her performance as Elle Woods in Legally Blonde, but this blonde beauty is the total opposite of the stereotypical California valley girl. Born in New Orleans, Louisiana and raised in Tennessee, Witherspoon is proud of her Southern roots. The Hollywood golden girl considers herself a Southern Belle, which was undoubtedly useful while starring as June Carter Cash in the critically acclaimed Johnny Cash biopic, Walk the Line. Pulling off a genuinely convincing Southern accent is no easy feat, but this Southern Belle turned Hollywood A-lister was more than capable to take on the challenge. 


When Witherspoon was nominated for her performance as June Carter Cash — her first Academy Award nomination and win — the actress took the opportunity to add a touch of Southern class to her special evening. Witherspoon donned a vintage Christian Dior beaded ball gown from 1955 with a plunging, draped neckline and intricate floral details fit for a Southern debutante. 

2007: Jennifer Hudson is a total dream girl

Dreamgirls was the film of 2007. It was a movie that had everything you could ever hope for in a cinematic musical masterpiece — incredible musical numbers, unforgettable performances, and the queen herself – Beyoncé. Not only did Dreamgirls gift the world with powerful, gut-wrenching ballads, which inspired many amateur performances in showers and cars across the country — Dreamgirls proved that Jennifer Hudson was far more than a reality television star. 


Just a few short years after her first American Idol audition, 25-year-old Hudson was ready to prove that she was worth more than fifteen silly minutes of fame. She knew she was a multi-talented powerhouse — and when Dreamgirls premiered, everyone else finally knew, too. Hudson won the Oscar for Best Supporting Actress at the 79th Academy Awards in 2007, accepting the award in a simple Oscar de la Renta gown that was pretty, though hardly worthy of Hudson's glory, to be honest. Thankfully, she changed into a glimmering gold, art deco style gown for the Vanity Fair Oscar Party and looked every bit the Oscar winning actress she finally was. 

2008: Heidi Klum is the red (carpet) queen

Supermodel Heidi Klum is no stranger to dropping jaws and turning heads wherever she goes. She's also no stranger to style, as six seasons of her hit show, Project Runway, have proved. So it should come as no surprise that Klum is a woman who knows how to dress for any occasion — especially red carpets. 


At the 80th Academy Awards in 2008, Klum arrived to the red carpet ready to make quite the fashion statement in a dramatic, sweeping, bright red ball gown by John Galliano Haute Couture. Her famous blonde locks were pulled into a wrap bun reminiscent of Hollywood starlet-turned-princess, Grace Kelly. The incredible gown featured a draping neckline that skimmed the nape of the supermodel's neck, giving off total Red Queen vibes. Though Klum wasn't nominated for an Academy Award, she absolutely stole the show in this unforgettable, fire engine red ball gown. Is it hot in here, or is it just her?

2009: Penelope Cruz breaks a record in a ball gown

Penelope Cruz arrived to the red carpet at the 81st Academy Awards in 2009 looking like a beautiful runaway bride. The Spanish-born actress stunned the crowd in an off-white, floor-length, vintage Balmain ball gown featuring a feathered skirt and intricate silver embroidery that was fit for a princess bride. Though it wasn't Cruz's wedding day, the actress had just arrived at what was soon to become quite the momentous (and historic) occasion. 


Cruz was nominated for the Best Supporting Actress Oscar for her performance in the Woody Allen movie, Vicky Cristina Barcelona. If she were to win the Oscar, she'd be the first-ever Spanish actress to do so. This was undoubtedly at the forefront of the actress' mind as she prepared for the big night. What do you wear to what could very well be the most important night of your career? This vintage Balmain gown would totally make the shortlist. Cruz looked absolutely exquisite while accepting her Oscar and breaking down barriers. 

2010: Jennifer Lopez is on cloud nine

Like we said earlier, Jennifer Lopez is a woman who knows how to dress. The Armani Privé ball gown the songstress/actress wore to the 82nd Academy Awards is the reason why Lopez is totally deserving of a second spot on this list. At the 2010 awards ceremony, Lopez looked like an actual angel in the icy-pink ball gown from Armani Privé's Spring collection. The designer dress featured an asymmetrical neckline and a hidden high slit to show off those famous gams. The train of the gown was accented with sparkling Swarovski crystals, because what woman doesn't love sparkling things? 


This princess dress was fairly modest compared to the red carpet looks of Lopez's past, proving that this is a woman who can pull off any style. When asked during a red carpet interview what she thinks makes a great Oscars dress, Lopez responded, "You have to feel good it in, you know? It just kind of has to have that wow factor." Write that down!

2011: Jennifer Lawrence makes her Oscars debut

Before Jennifer Lawrence stole hearts with her disarming personality and unabashed love for pizza, she was a fresh-faced young actress making her red carpet debut in an absolutely breathtaking fashion. The 20-year-old actress was nominated for her very first Oscar at the 83rd Academy Awards for her critically-acclaimed, breakout performance in the indie drama, Winter's Bone


Lawrence may be a household name these days, but she was relatively unknown when she first stepped onto the red carpet in 2011 wearing a bright red, figure-hugging, custom Calvin Klein number. Obviously a lot of effort goes into preparing for an event like the Academy Awards, but Lawrence looked effortlessly flawless. Her long, loosely-waved blonde locks framed her face, and she opted for a classic nude lip and smokey eye. 

In an interview with Chris Harrison on the red carpet, Lawrence joked, "I'm so happy to be here. I can't wait to use my losing face. Now, if I win, I won't be able to use it!" While she didn't win the Oscar in 2011, it was only a matter of time before the red carpet charmer would have to master her winning face. 


2012: Angelina Jolie strikes a pose

There were hundreds of celebrities in attendance at the 84th Academy Awards, but the star of the show was most definitely Angelina Jolie's leg. The bombshell A-lister was technically there to present the Academy Award for Best Original Screenplay, but she was also there to serve some serious leg, honey. 


Jolie donned a black Atelier Versace gown with a folded, asymmetrical neckline and a thigh-high slit perfect for striking a pose and showing off her gams. Nearly every picture you'll see of Jolie from the 2012 awards ceremony will show the actress with her hand planted firmly on her jutted hip, and her (now infamous) leg with bended knee peeking through the slit of her Atelier Versace ball gown. As always, she looked absolutely gorgeous, but her dramatic, slightly awkward pose did not go unnoticed by the media-sphere. Leave it to Jolie to steal the show using only her leg.

2013: Jennifer Lawrence takes a tumble in Dior

The 85th Academy Awards ceremony was Jennifer Lawrence's night to shine, try out her winning face, and take a tumble on national television. The actress, nominated for the Best Actress Oscar for her performance in Silver Linings Playbook, arrived at the 2013 awards ceremony looking as regal as ever in a strapless, pale-pink Dior Couture gown, featuring a stunning mermaid silhouette and flowing train. She gave a series of hilarious red carpet interviews that almost immediately secured her title of America's Sweetheart, but Lawrence's charm didn't stop there. 


When she was announced as the Best Actress Oscar winner, Lawrence was visibly shocked. She stood and hugged her loved ones, mouth agape in disbelief, before making her way to the staircase standing between herself and the stage. Poor Lawrence barely made it up one stair before she tripped over the her sweeping gown — luckily, though, this gal has a sense of humor. In an interview after her win, a reporter asked Lawrence what was going through her mind when she fell down. "Uh, a bad word," the new Oscar winner responded. At least she fell in style! 

2014: Lupita Nyong'o stuns in a gorgeous Grecian goddess gown

Is this dress giving you total fairytale vibes? Luptia Nyong'o, winner of the Best Supporting Actress Oscar for her performance in Steve McQueen's 12 Years a Slave, arrived to the 86th Academy Awards wearing this custom-made, light blue Prada gown — the epitome of a Cinderella dress. The pale blue gown featured a plunging deep V neckline, an empire waist, and a flowing, beaded train. The Kenyan-Mexican actress told Ryan Seacrest during a red carpet interview that she chose the pale blue color because it reminded her of Nairobi, her Kenyan hometown. To top it all off, Nyong'o donned a dainty diamond Fred Leighton headband. The added touch of elegance, reminiscent of a tiara, only confirmed that Nyong'o is an actual princess and we are not deserving.


In true fairytale princess fashion, Nyong'o used her acceptance speech to spark a flame of inspiration within the hearts of audiences worldwide, saying, "When I look down at this golden statue, may it remind me and every little child that no matter where you're from, your dreams are valid." Disney princesses are real. 

2015: Lady Gaga makes a show-stealing statement

Lady Gaga is famous for not only her powerhouse talent, but for her dramatic, show-stealing, and sometimes downright bizarre outfits. From her veiled red lace ensemble (complete with a crown), to the infamous meat dress she wore to the 2010 Video Music Awards, Gaga has carved a place for herself amongst the most eclectic red carpet attendees. 


However, when she arrived to the 87th Academy Awards in 2015, the songstress appeared to have chosen a uncharacteristically simplistic ball gown from designer Azzedine Alaia. According to Vogue, Gaga's 2015 red carpet appearance was the first time one of Alaia's made-to-measure gowns was worn to the Academy Awards. The multi-talented star looked simply elegant in the sweeping, floor-length ball gown, which featured extra wide sleeves, an empire waist, and beaded metallic intricacies. Though the look was muted for Gaga, the platinum blonde beauty made a statement with elbow-length red rubber gloves and a bold, red lip to match. 

This stunner was only one of the three Alaia designs Gaga donned throughout the evening. The second outfit, a heavenly halter gown in feather-white, made its debut during Gaga's incredible Sound of Music performance — a memorable music moment for which she received a standing ovation. The third came in the form of a black, figure-hugging, floor-length number that Gaga wore to the Vanity Fair Oscar Party. A little (outfit) change never hurt anyone — and Gaga proves it.


2016: Mindy Kaling is black, blue, and beautiful all over

Some people would have you believe that wearing black and blue together is some type of cardinal sin. Not only are those people incredibly mistaken — they obviously haven't seen the breathtaking black and blue gown worn by Hollywood it-girl, actress and writer Mindy Kaling. 


The Office alum, who voiced Disgust in the Academy Award winning animated movie, Inside Out, wowed the crowd when she stepped foot onto the red carpet at the 88th Academy Awards in 2016. Designed by Elizabeth Kennedy, the off-shoulder number featured a floor-length black gown that perfectly showcased the star's curves, as well as a dramatic and flowing royal blue train. The Mindy Project star proved that less really is more by accessorizing simplistically, donning a pair of diamond drop earrings and wearing a single sapphire and diamond ring — both jewelry pieces furnished by Effy. 

In a red carpet interview with Ryan Seacrest, Kaling joked about her Oscar prep process, saying, "I've been [getting ready] for, like, 72 hours. I'm the most high maintenance person in the world." No matter how long she spent preparing, Kaling looked every bit the part of a bonafide, effortlessly glamorous leading lady. 


2017: Emma Stone is old school Hollywood glam

Emma Stone, the charming red-haired beauty who broke into the scene with her role in the coming-of-age comedy Superbadfound herself a two-time Academy Award nominee in 2017 for her performance in the critically acclaimed Damien Chazelle musical, La La Land. Stone's second Oscar nomination came merely two years after she first became a Best Supporting Actress nominee for her performance in Birdman. At only 28 years old, Stone had had more success than most actors see in a lifetime of work. Praised for her work in La La Land — a musical which quickly proved her to be a triple threat — Stone was predicted to take home the coveted golden statue. What better way to will an Oscar win into existence than by dressing as an Oscar? 


Stone stepped onto the red carpet at the 89th Academy Awards donning a golden Givenchy Haute Couture gown embroidered with sparkling Swarovski crystals. The gown's mermaid silhouette hugged the starlet's svelte figure and featured a layered fringe skirt reminiscent of a Roaring Twenties flapper dress. When Stone delivered her emotional acceptance speech upon winning the Best Actress Oscar, she very much resembled a golden and glamorous statue herself. These two are total #twingoals.