40 Unforgettable Red Carpet Looks That Went Down In Oscars History

The Academy Awards is the movie industry’s blue riband event, and everyone there is desperate to make a big impression. But aside from actually winning a gold statuette, the best way to make headlines is to strut your stuff on that famous red carpet. Yes, the fabulous fashion on display is a major part of every Oscars night. So, showcasing everything from the timeless classics to the revealing and the downright outrageous, here are 40 of the most memorable outfits worn on Hollywood’s biggest night of the year…

40. Barbra Streisand (1969)

After the 1969 Academy Awards, there were two things everyone was talking about with regards to Barbra Streisand. Firstly, she tied for Best Actress with Katharine Hepburn. Secondly, the actress and singer’s zany outfit – created by Arnold Scaasi – was somewhat transparent. But to be fair to Streisand, she apparently had no idea just how see-through it would prove as the flashes fired and the camera shutters clicked.

39. Taraji P. Henson (2018)

Empire star Taraji P. Henson rocked up to the 2018 Oscars wearing a black Vera Wang dress with a very daring slit and necklace. But one month later the star told Entertainment Tonight that the gown could have been even more scandalous. She said, “I’m not afraid. Vera was like, ‘Let’s take it there!’ Wangy bangy, baby.”

ADVERTISEMENT

38. Jennifer Lawrence (2013)

Jennifer Lawrence wore a Dior Couture dress while accepting a Best Actress award at the 2013 Oscars. But it famously caused her a problem. You see, the star fell over as she walked to the stage to collect her gong for Silver Linings Playbook. It turned out, Lawrence later revealed to British newspaper The Independent, that dreams of cake meant that she had momentarily forgotten her stylist’s prescient advice that she should kick the fabric away from her legs as she moved.

37. Gemma Chan (2019)

ADVERTISEMENT

Crazy Rich Asians actress Gemma Chan chose an eye-catching Valentino gown for the 2019 Oscars. It was unique in many ways: it was large; it had a high collar; it was bright pink; and it had pockets. Chan admitted later that she’d used the pockets to hide snacks she could eat during the long ceremony.

36. Jayne Mansfield (1956)

The fashion rules in 1956 were, of course, more conservative than they are now – but that didn’t stop Jayne Mansfield. That year, you see, the blonde bombshell posed in a daring dress in front of an Oscar statue with Cleo Moore. The look created one of the most fabulous Academy Award photographs of all time.

ADVERTISEMENT

35. Uma Thurman (2004)

ADVERTISEMENT

For the 2004 Academy Awards, Uma Thurman decided to wear a white lacy Christian Lacroix dress that billowed out everywhere. And according to the subsequent press, the gown didn’t flatter her in the slightest. The media actually dubbed the look “Swiss Miss,” and Thurman herself later expressed dissatisfaction with it. But no matter what else, the look certainly wasn’t boring.

34. Penélope Cruz (2007)

Penélope Cruz dazzled audiences in 2007 when she showed up to the Academy Awards in a pink Atelier Versace dress with a feathered train. Everyone was impressed. In fact, in February 2019 – over a decade after the fact – The Daily Telegraph declared that the gown was “everything and more than you could ever want from an Oscars dress.”

ADVERTISEMENT

33. Kim Basinger (1990)

ADVERTISEMENT

Batman actress Kim Basinger tried something new and very unusual for the 1990 Oscars. In fact, she wore a white gown/tuxedo hybrid, complete with just one glove. The star even designed it herself! And while many contemporary fashion critics mocked the look, the outfit is still being talked about even today. So clearly Basinger had the last laugh.

32. Charlize Theron (2019)

Charlize Theron had three things to show off at the 2019 Academy Awards: brown hair, shoulder blades, and a dress that complimented both. So Theron’s chosen gown was a light blue design from the Haute Couture Christian Dior collection. The stunning creation was wide open at the back and certainly got the job done.

ADVERTISEMENT

31. Kate Hudson (2001)

ADVERTISEMENT

When Kate Hudson attended the 2001 ceremony, her dress didn’t meet with much approval. In 2014, though, the actress told the Evening Standard, “I was 21 years old when I was nominated for an Oscar for Almost Famous and to have Stella McCartney dressing me for the ceremony I felt like the hippest, coolest girl in the world. I woke up the next morning and turned on the television to find out I was on every worst-dressed list. So I called Stella, and we just laughed our *sses off.”

30. Diane Keaton (2004)

Diane Keaton decided not to wear a dress for the 2004 Academy Awards and opted instead for a Ralph Lauren suit and bowler hat. Yet it wasn’t the first time that she’d done such a thing, as she’d worn a white suit in 1978 when the star won her Oscar for Annie Hall. And while some loved the look, some hated it. But either way, it was extremely memorable.

ADVERTISEMENT

29. Gwyneth Paltrow (2002)

ADVERTISEMENT

When Gwyneth Paltrow arrived for the 2002 Oscars, people noticed that her sheer Alexander McQueen dress was maybe a little too revealing. Paltrow thought so, too, and wrote on her website in 2013, “I still love the dress itself, but I should have worn a bra, and I should have just had simple beachy hair and less make-up.”

28. Lizzy Gardiner (1995)

Costume designer Lizzy Gardiner wished to feature a dress made out of American Express cards for The Adventures of Priscilla, Queen of the Desert, but the company wouldn’t let her. They did, however, let her wear said dress to the 1995 Oscars – where it gained plenty of attention. In 1999, in fact, the gown was auctioned off, with the money going to an AIDS research foundation.

ADVERTISEMENT

27. Shanina Shaik (2019)

ADVERTISEMENT

Model Shanina Shaik wore a stunning Maison Yeya dress to a 2019 Oscars afterparty. She might not be wearing it again, though, because she suffered not one but two wardrobe malfunctions while walking the red carpet. First, the front part came out and exposed too much. And then the slit on the leg revealed her underwear. Oops!

26. Cate Blanchett (2016)

Cate Blanchett, nominated as Best Actress for Carol, rocked something both beautiful and unusual on the 2016 Oscars red carpet. Indeed, she wore a seafoam-green gown decorated with fabric flowers, a creation of Armani Privé. Vanity Fair declared at the time, “Scientists have proven it is impossible to look at this dress and not gasp and then remain speechless for at least ten seconds.”

ADVERTISEMENT

25. Edy Williams (1974)

ADVERTISEMENT

Edy Williams was one of the most scandalous actresses of her era. During the 1974 Academy Awards, for instance, she pulled her fur coat off to reveal nothing but a leopard-skin bikini underneath. She would probably have shown the most skin of the whole ceremony if a streaker called Robert Opel hadn’t later run across the stage.

24. Cher (1974)

Over the years, Cher has made a habit of wearing weird, wacky outfits to the Oscars. For sheer daring, though, her 1974 ensemble takes the cake. After all, that’s the year she wore a colorful sarong-like skirt and a bikini-like top designed by Bob Mackie. It’s a style that wouldn’t have looked out of place on a sunny beach somewhere.

ADVERTISEMENT

23. Marion Cotillard (2008)

ADVERTISEMENT

In 2008 Marion Cotillard channeled her inner mermaid and wore a beautiful Jean Paul Gaultier dress designed to look like fish scales. It turned out to be an extremely good night for Cotillard, too. Not only did her gown win acclaim, but the star also picked up the Best Actress Oscar for playing Édith Piaf in La Vie en Rose.

22. Whoopi Goldberg (1993)

Whoopi Goldberg might just take home the award for the most colorful Oscars outfit of all time. Back in 1993, you see, Goldberg was hosting the ceremony and wore a purple satin coat that opened up to reveal a cascade of bright green. Apparently, the actress had simply bought the dress in a boutique.

ADVERTISEMENT

21. Angelina Jolie (2000)

ADVERTISEMENT

People might have mistaken Angelina Jolie for Morticia Addams when she picked up her Oscar for Girl, Interrupted in 2000. After all, the star wore a gothy black Versace gown and even had black hair extensions put in. Yet it wasn’t the outfit that grabbed all the headlines – for that was the year Jolie kissed her brother on the Oscars red carpet.

20. Sharon Stone (1998)

Sharon Stone decided to wear something a bit different for the 1998 Oscars. In fact, she paired an attractive lavender Vera Wang skirt with an ordinary white Gap shirt that belonged to her spouse, Phil Bronstein. The media were totally shocked – but the look went down in Academy Awards history.

ADVERTISEMENT

19. Cher (1988)

ADVERTISEMENT

Cher and her fashion collaborator Bob Mackie created a sheer black dress for the 1988 Academy Awards – a very sheer black dress. In fact, when Cher went up on stage to accept her Best Actress award for Moonstruck, the outfit left nothing to the imagination. It was all completely outrageous – and made for an iconic Oscars moment.

18. Lupita Nyong’o (2015)

Lupita Nyong’o wore a showstopper for the 2015 Oscars, in which she served as one of the presenters. The dress was a Calvin Klein creation featuring 6,000 white Akoya pearls, and it was worth at least $150,000. It actually caught the attention of criminals, too. A week after the ceremony, in fact, the outfit was stolen from Nyong’o’s hotel room. Fortunately, though, the gown was located in the end.

ADVERTISEMENT

17. Maya Rudolph (2019)

ADVERTISEMENT

Pink seemed to be the color of choice at the 2019 Academy Awards. Yet Bridemaids actress Maya Rudolph put a slightly different spin on things and wore pink florals instead with her Giambattista Valli gown. Alas, Rudolph was slammed as one of the worst-dressed stars of the night by users of Twitter. The dress was, however, seriously on-trend.

16. Nicole Kidman (2007)

Nicole Kidman opted for a bright red Balenciaga dress when she attended the 2007 Academy Awards. The gown was striking enough on its own, but it also happened to have a massive train-like bow attached to it. And while it met with rather mixed reviews at the time, the style is now considered one of Kidman’s best-ever looks.

ADVERTISEMENT

15. Geena Davis (1992)

ADVERTISEMENT

Geena Davis was nominated for Thelma & Louise in 1992, but for the Oscars ceremony she wore a dress she probably wouldn’t even have been able to drive a car in. It was a short, ruffled affair created by Ruth Meyers and Bill Hargate. Davis topped off the look with some long satin gloves and black tights. It was, if nothing else, very ’90s.

14. Michelle Williams (2006)

Actress Michelle Williams attended the 2006 Academy Awards with her boyfriend Heath Ledger, with whom she’d had a baby daughter just three months previously. Her chosen yellow Vera Wang dress delivered – and then some – on the red carpet. In fact, the gown was so acclaimed by the fashion industry that it even has its own Wikipedia page.

ADVERTISEMENT

13. Céline Dion (1999)

ADVERTISEMENT

Céline Dion stunned onlookers when she wore a Christian Dior tuxedo backward at the 1999 Academy Awards. Her song “The Prayer” from Quest for Camelot was nominated for an award, but it was the suit – specifically designed to be worn back-to-front – that drew attention. Dion also wore diamond-encrusted Ray-Bans in exchange for a charitable donation from the company.

12. Kerry Washington (2016)

Scandal star Kerry Washington wore a risqué Atelier Versace dress for the 2016 Oscars. And not only did it have a slit in the skirt up to her thigh, but it also included a leather bodice. Elle magazine wrote at the time, “The hard-and-soft combo brings some necessary edge to the red carpet.”

ADVERTISEMENT

11. Jennifer Lopez (2012)

ADVERTISEMENT

Jennifer Lopez arrived at the 2012 Academy Awards wearing a sparkling, silk Zuhair Murad gown decorated with crystal beads. It was beautiful – but the neckline may have been a little too low. As she presented the Oscar for Best Costume Design, in fact, people thought they saw a wardrobe malfunction take place.

10. Charlize Theron (2016)

For the 2016 Oscars, Charlize Theron wore a bright red Dior Haute Couture dress. She hadn’t actually seen it until two weeks before the event took place, because she had been off filming in Germany. But it’s probably safe to say that she was happy with it. After all, the plunging neckline showed off a 48.8-carat Harry Winston necklace.

ADVERTISEMENT

9. Billy Porter (2019)

ADVERTISEMENT

Not many men wear dresses on the red carpet, but Billy Porter is one who did. Yes, in 2019 he wore a spectacular Christian Siriano tux-gown to the Academy Awards. He told Vogue magazine that same year, “We wanted to play between the masculine and the feminine. This look was interesting because it’s not drag. I’m not a drag queen; I’m a man in a dress.”

8. Angelina Jolie (2012)

Angelina Jolie wore a black Versace dress to the Oscars in 2012 and virtually created a whole movement. The sight of her leg sticking out of the elegant slit caused internet-fuelled chaos, in fact. And before too long someone had set up a Twitter account devoted exclusively to Jolie’s leg – and it quickly gained 28,000 followers.

ADVERTISEMENT

7. Lupita Nyong’o (2014)

ADVERTISEMENT

The year 2014 was a very good one for Lupita Nyong’o. After being nominated for her performance in 12 Years a Slave, the actress took to the Oscars red carpet in a blue Grecian-style Prada dress that established her as a fashion icon. The gown was, she said, inspired by her hometown of Nairobi. Nyong’o also won the Best Supporting Actress award that night.

6. Mariah Carey (2017)

Singer Mariah Carey went to the 2017 Vanity Fair Oscars Party wearing a green chiffon dress created by Philipp Plein. Some people raised eyebrows about how much cleavage and leg it showed, but when Plein posted a picture of Carey in the dress on Instagram, everyone seemed to voice their approval.

ADVERTISEMENT

5. Cate Blanchett (2011)

ADVERTISEMENT

Cate Blanchett’s dress for the 2011 Oscars won her lots of praise. It was a creation by Versace, and the actress utterly loved it. As she told InStyle that April, “It was so architectural, and the breast piece is made all out of elastic. The color combination, I couldn’t believe it when I saw it in real life.”

4. Cindy Crawford (1991)

In 1991 supermodel Cindy Crawford stepped out on the Oscars carpet, with Richard Gere on her arm, in a plunging red Versace dress. It became mega-famous, boosting the profiles of both Crawford and Gere. And such was its influence that multiple copies were quickly produced. To this day, in fact, it regularly ranks highly in polls of the greatest dresses ever worn.

ADVERTISEMENT

3. Björk (2001)

ADVERTISEMENT

Famous musician Björk wore a curious creation for the 2001 Oscars ceremony: a gown that would become known as the “swan dress.” The dress was designed by Marjan Pejoski to look like a giant swan, and on her walk down the red carpet Björk dropped golden eggs. It was all very weird – but it’s still remembered as an interesting piece of fashion history.

2. Halle Berry (2002)

Halle Berry’s dress for the 2002 Academy Awards became known as “the Elie Saab net dress,” so-called because of its mesh design. It was beautiful, form-fitting and a massive success. It’s even considered one of the best Oscar dresses ever made. Plus, Berry won Best Actress that night, becoming the first black woman to accomplish the feat.

ADVERTISEMENT

1. Cher (1986)

ADVERTISEMENT

After losing out on a Best Actress nomination for the 1986 Oscars, Cher decided to show up anyway and blow everybody away with a show-stopping outfit. She asked Bob Mackie to create a black showgirl-style outfit with a massive headpiece – and the resulting dress immediately found a place in the annals of fashion history.

Yet it’s not just Hollywood stars who turn heads with their entrancing outfits. Whenever a royal wedding is announced, in fact, many thoughts go straight away to the dress. Who will design it? What will it look like? Will it start a new trend among brides? And people are right to think that way, as royal wedding dresses almost always go on to be iconic in their countries of origin. These 20 gowns, for example, are some of the most awe-inspiring ever to have been worn by queens and princesses.

ADVERTISEMENT

20. Princess Claire of Luxembourg

ADVERTISEMENT

Princess Claire of Luxembourg, known before her marriage to Prince Felix as Claire Lademacher, actually technically got two royal wedding ceremonies: a civil one and a religious one. But she saved her gorgeous Elie Saab-designed silk gown for the latter, which took place in France on September 21, 2013. It’s stunningly chic!

19. Marie-Chantal, Crown Princess of Greece, Princess of Denmark

The nuptials of Pavlos, Crown Prince of Greece, and Marie-Chantal Miller were a million-dollar affair that saw multiple monarchs gather in London on July 1, 1995. So, naturally, there was no scrimping on the wedding dress. Apparently, Miller’s Valentino gown was worth $225,000 and took 25 people four months to make.

ADVERTISEMENT

18. Princess Margaret, Countess of Snowdon

ADVERTISEMENT

Princess Margaret married photographer Antony Armstrong-Jones in May 1960, but the couple were divorced by 1978. However, that doesn’t take away from the beauty of Margaret’s simple but divine silk organza gown. It was created by famous dressmaker Norman Hartnell, and these days it’s on display in Kensington Palace.

17. Queen Jetsun Pema of Bhutan

When King of Bhutan Jigme Khesar Namgyel Wangchuck wed Jetsun Pema on October 13, 2011, it was a beautifully colorful occasion. The new queen donned a kira, the traditional attire for women in Bhutan, and it helped turn her into a style icon across the world.

ADVERTISEMENT

16. Princess Mabel of Orange-Nassau

ADVERTISEMENT

When Prince Friso and controversial “commoner” Mabel Wisse Smit married on April 24, 2004, the bride wore a magnificently ostentatious dress by wacky Dutch designers Viktor & Rolf. Notably, it had 248 handcrafted crepe georgette bows on it. And while that by itself sounds weird, the gown nevertheless looked great on her.

15. Stéphanie, Hereditary Grand Duchess of Luxembourg

Countess Stéphanie de Lannoy gained a few more titles when she married Guillaume, the heir apparent of Luxembourg. Their religious wedding ceremony took place on October 20, 2012. And Stéphanie practically shone in an Elie Saab dress that boasted 50,000 pearls and 80,000 crystals.

ADVERTISEMENT

14. Princess Noor bint Asem

ADVERTISEMENT

The marriage between Prince Hamzah and Princess Noor bint Asem, his second cousin, unfortunately didn’t last very long. The couple got spliced on August 29, 2003, and were divorced six years later. But hopefully the princess got to keep her sparkling white wedding dress, as it was stunning.

13. Princess Sofia of Sweden

When former glamor model Sofia Hellqvist married Prince Carl Philip in June 2015, she had a lot to prove. So she played it safe with a smart white lace gown designed by fellow Swede Ida Sjöstedt. However, in a nod to her wild past, she made sure her back tattoo remained visible while she wore it.

ADVERTISEMENT

12. Princess Frederica of Hanover

ADVERTISEMENT

Princess Frederica of Hanover married her first cousin once removed, Prince Paul of Greece, back in January 1938. But her wedding dress still stands up today! The elegant creation looked great with her tiara, which was handed down to her from Princess Sophie of Prussia.

11. Princess Elizabeth

Princess – later Queen – Elizabeth and Philip Mountbatten married on November 20, 1947, a time when rationing was still taking place in Britain. And incredibly, despite the British royal family’s wealth, ration coupons were still needed to buy the material! The result, though, made the effort worthwhile, as Elizabeth wed in a beautiful satin Norman Hartnell creation decorated with crystals and pearls.

ADVERTISEMENT

10. Princess Salwa Aga Khan

ADVERTISEMENT

In August 2013 model Kendra Spears found herself living every girl’s dream when she married the fabulously wealthy Prince Rahim Aga Khan, son of the Aga Khan IV. Taking the name Salwa Aga Khan on marriage, she dazzled everyone in her fabulous Manav Gangwani-designed sari on her big day.

9. Princess Charlene of Monaco

When Prince Albert II of Monaco married swimmer Charlene Wittstock in July 2011, the country threw a massive party. And, needless to say, her dress was cause for celebration, too. It was an Armani creation featuring 40,000 Swarovski crystals, 20,000 pearls and, to top it all off, 30,000 gold stones.

ADVERTISEMENT

8. Princess Hajah Hafizah Sururul Bolkiah

ADVERTISEMENT

Princess Hajah Hafizah Sururul Bolkiah is daughter to the Sultan of Brunei, one of the richest men in the world, so it goes without saying that her wedding dress was something amazing. When she wed Pengiran Haji Muhammad Ruzaini on September 23, 2012, she wore a lavishly jewel-encrusted gold outfit.

7. Princess Mette-Marit of Norway

Princess Mette-Marit has a classic rags-to-riches life story; she was a waitress with a druggy background before she married Crown Prince Haakon of Norway in August 2001. So, naturally, her dress was a fairytale one, too. It was designed by Ove Harder Finseth and made of luxurious silk.

ADVERTISEMENT

6. Princess Rania of Jordan

ADVERTISEMENT

Rania Yassine became a princess – and, a few years later, a queen – when she married Prince Abdullah on June 10, 1993. For her wedding ceremony she chose a dress designed by Brit Bruce Oldfield: an unusual but formal gown with gold embroidery.

5. Crown Princess Máxima of the Netherlands

Máxima Zorreguieta chose world-famous designer Valentino to design her wedding gown, and the result was a huge success. She stepped out in a eye-catching Mikado silk frock on February 2, 2002, and the result instantly made Valentino the number one choice for European royal wedding dresses.

ADVERTISEMENT

4. Sarah, Crown Princess of Brunei

ADVERTISEMENT

In September 2004 an event dubbed “the Asian wedding of the year” took place. What’s more, the marriage of Prince al-Muhtadee Billah of Brunei and Sarah Pengiran Salleh cost millions of dollars. The bride’s stunning blue outfit was decorated with gemstones and diamonds; even her bouquet was made of gold!

3. Diana, Princess of Wales

As we know, the marriage between Diana and Prince Charles wasn’t a happy one. But when it took place in July 1981, it seemed like a dream come true. Diana wore a dress of exquisite antique lace created by Elizabeth and David Emanuel, its price tag in the thousands.

ADVERTISEMENT

2. Grace Kelly, Princess of Monaco

ADVERTISEMENT

Hollywood actress Grace Kelly became the archetypal princess when she married Prince Rainer of Monaco in April 1956. As befitting the bride’s career, her Brussels lace wedding dress was designed by Oscar-winning dressmaker Helen Rose. And it still looks magnificent over 60 years later.

1. Catherine, Duchess of Cambridge

When Kate Middleton married Prince William on April 29, 2011, all eyes were on the wedding dress. Luckily, it didn’t disappoint. Designed by Sarah Burton of Alexander McQueen, it was a bewitching construction of satin and lace that instantly went down in history.

ADVERTISEMENT
ADVERTISEMENT