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Emily Smith

The 32 most surprising red carpet looks of all time - from outrageous gowns to famous fashion faux pas

Composite image of Zenday, Lady Gaga, Britney Spears and Justin Timberlake, Billy Porter and Kim Kardashian.

When it comes to delivering a jaw-dropping fashion statement on the red carpet, you can count on these celebrities. Double denim, feathers or latex, they've worn it all. 

When we think of the best red carpet looks, stunning floor-length gowns and sharp suits immediately spring to mind. However, when it comes to the more outrageous outfits, there is a group of specific celebs like Lady Gaga, Billy Porter and Kim Kardashian who we can count on to push the boundaries of red-carpet attire. 

From some of the most unforgettable Met Gala looks to controversial fashion faux pas, these outfits are the most surprising (and outrageous) looks we've seen on the red carpet through the years. 

1. Britney Spears and Justin Timberlake - AMAs, 2001

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For the 2001 American Music Awards, the then-couple of the time Britney Spears and Justin Timberlake rocked up in matching denim ensembles. Styled by Steven Gerstein, the two pop stars will forever be remembered as the king and queen of the Canadian Tuxedo. 

2. Bjork - Oscars, 2001

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Perhaps one of the most iconic red carpet looks of all time, Bjork truly made history when she wore the unique dress for the 2001 Oscars. The dress was designed by Macedonian designer Marjan Pejoski and has since become a memorable cult classic.

3. Lady Gaga - MTV VMAs, 2010

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Lady Gaga truly shocked the world at the 2010 MTV Video Music Awards when she donned a dress, shoes and headpiece made completely from raw beef. Franc Fernandez designed the outfit, and it was an instant talking point - not to mention, pretty controversial among animal rights groups...

4. Kim Kardashian - Met Gala, 2021

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Arriving with then-husband Kanye West, Kim Kardashian's look at the 2021 Met Gala made huge media waves. The blackout gown was one-of-a-kind and left the reality star covered from head to toe in a black jersey material. It was designed by Balenciaga's creative director Demna Gvasalia. 

5. Cher - Oscars, 1986

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Now known as her 'revenge dress', Cher's iconic black sequined outfit that she wore to the 1986 Oscars was designed by Bob Mackie and was reportedly worn as a protest against the Academy who had snubbed her performance in Mask. The feathered headdress was truly the star of the show as it towered above her. 

6. Billy Porter - Met Gala, 2019

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Known for his fashion statements, Billy Porter stole the show at the 2019 Met Gala. His arrival on a plush litter carried by six shirtless men was a nod to Egyptian culture, as was his head-to-toe golden look. The wings were an impressive 10 foot long and his headpiece was made of a mind-blowing 24-karat gold. 

7. Barbara Streisand - Academy Awards, 1969

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Attending the 1969 Oscars, icon Barbara Streisand wore a rather controversial see-through sequined pantsuit. The outfit, designed by Arnold Scaasi, has 70s-esque flared legs and tuxedo cuffs. It turns out that Streisand was actually unaware of just how see-through the pantsuit was and has since come out to say she was horrified when the lights hit the fabric. 

"I was choosing between two different outfits. One was lovely but very conservative. And then there was the pantsuit with plastic sequins," she told W Magazine. "I had no idea that when the lights hit that outfit, it would become transparent! I wanted a white collar and cuffs, which it had, and I wore my hair under my chin, because I thought to myself, I’m going to win two Oscars in my lifetime, and I’ll be more conservative next time."

8. Sarah Jessica Parker - Met Gala, 2018

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One of Sarah Jessica Parker's best looks, we just know this gown is a look Carrie Bradshaw would be proud of. The golden ensemble the actress wore to the 2018 Met Gala was truly a sight to behold and was perfect for the Heavenly Bodies theme that year. The luxurious gown was courtesy of Dolce & Gabbana and SJP completed the look with a matching ornate headpiece. 

9. Madonna - Grammys, 2015

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It's not surprising that the original material girl knows how to sport a sassy and shocking look. For the 2015 Grammys, the iconic singer worked a rather revealing couture look heavily inspired by the traditional dress of a Spanish Matador. She wore the fun Givenchy frock with a pair of fishnet tights and leather knee-high boots. 

It wasn't the first time the singer had dressed as a Matador - in the music video of her 1994 hit 'Take a Bow', she portrayed the bereft lover of a famous bullfighter, and then she took on the role herself (sort of) in her 2015 'Living for Love' video.

10. Nicki Minaj - MTV VMAs, 2011

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Nicki Minaj has never been a 'less is more' sort of fashionista and this outfit is a perfect example of that. The rapper wore this maximalist get-up to the 2011 MTV VMAs, not only did the outfit consist of a metallic corset and face mask but she also paired it with a chain of sewn-together stuffed animals. 

11. Katy Perry - Met Gala, 2010

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Katy Perry has always known how to make fashion fun and this light-up dress she wore to the 2010 MET Gala is no exception. Her dress didn't seem too revolutionary at first without its LED feature turned on, but that soon changed as the dress started to change colours. 

12. Celine Dion - Oscars, 1999

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Not the most controversial or groundbreaking look, but it caused quite a stir back in the day. Dion's 1999 Oscars outfit was dubbed as a fashion failure and was widely criticised. However, history has been kinder to the backwards tux look and it often features in round-ups of Celine Dion's most iconic looks.

13. Kim Kardashian - Met Gala, 2013

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This dress unfortunately wasn't so surprising because of how awe-inspiring it was but rather because it was considered a faux pas with social media users calling it old-fashioned and likening it to an old upholstered sofa. 

The floral maxi gown that Kim wore for the 2013 Met Gala was high-neck, long-sleeved and designed by Givenchy. It was Kim's first time at the distinguished event and the unfortunate reception to her outfit left her in tears. She recalled to US Vogue, "I was crying, like, the whole way home because I just couldn’t believe it. There were all these memes about me and this couch." 

14. Lara Flynn Boyle - Golden Globes, 2003

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Boyle wore a controversial ballerina-inspired look designed by David Cardona at the 2003 Golden Globe Awards. The look was met with a divided reaction, while some adored the look, others viewed it as a red carpet fashion mishap. 

15. Angelina Jolie - Oscars, 2012

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At first glance, this look from Angelina doesn't seem all that special or surprising however this particular moment (pictured) went viral online. The dress, designed by Donatella Versace, was a stunning strapless number with a thigh-high slit in the front. What was truly memorable was the way Angelina popped her leg out through the split. It drove the internet so wild that a Twitter account was made dedicated to the pose. 

16. Rihanna - Met Gala, 2017

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Living up to her name as Queen of the Met Gala, Rihanna wore one of the most surprising outfits we've ever seen from her. The 2017 Met Gala theme was Comme des Garçon: Art of the In-Between, so of course Rihanna nailed it with this Comme Des Garçons floral ensemble. 

17. Lady Gaga - Grammys, 2010

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Back in the day, there was no predicting what Lady Gaga would wear on the red carpet, so all of her looks - wild or tame - would come as a surprise. This galactic dress she wore to the 2010 Grammys could perhaps be considered one of her more tame looks, although this Giorgio Armani number certainly turned a lot of heads. It wasn't just the dress though - her gravity-defying shoes and very spiky prop sealed this look as one for the history books. 

18. Katy Perry - Met Gala, 2019

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The best Met Gala looks are always surprising as there's no telling how celebs will interpret the theme - and we'll never forget this one from singer Katy Perry.

For the 2019 Met Gala, where the theme was Camp: Notes on Fashion, Perry wore a mesmerising chandelier gown that had three tiers of working lights. The iconic dress was designed by Jeremy Scott who created the dress along with his team and hand-placed thousands of Swarovski crystals on the gown. 

19. Amber Heard - Aquaman London Premiere, 2017

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Amber Heard seriously dressed the part for the 2018 Aquaman London premiere and she donned a dress with a green scale-like pattern and a matching swim cap. Although the cap was deemed a rather strange accessory, if there's any premiere you can wear a swim cap to, it's Aquaman. 

20. Sarah Paulson - Oceans 8 Premiere, 2019

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Given the star-studded cast, it's no surprise that the Oceans 8 red carpet was packed with unforgettable looks. But Paulson's acid green Prada dress was rather unexpected.  The dress, from Prada's Fall 18 collection,  featured endless layers of plastic neon fringe and certainly made a statement. Rihanna even spoke about how jealous it made her - which is no mean feat!

21. Christina Aguilera - Bazaar Icons Party, 2018

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This one might give you a little deja vu, as it's not the first time the pop star has sported a statement feathered look. For the Bazaar Icons party in 2018, Christina wore a Vivienne Westwood dress which was covered head to toe in white feathers. She paired the eye-catching dress with a bold coral lip and matching red shoes. 

22. Rita Ora - MTV EMAs, 2017

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At the MTV European Music Awards in 2017 Rita Ora took 'keeping it casual' very literally as she turned up in a bathrobe and matching head towel. The singer dressed up the Palomo Span's bathrobe with diamond jewellery and a pair of blinged-out heels. 

23. Sam Smith - Brits, 2023

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Sam Smith chose fashion over functionality when they wore this inflatable latex jumpsuit to the 2023 Brit Awards. Made by the London-based fashion label Harri, Smith styled the jumpsuit with some matching platform heels, gloves and of course diamond earrings. 

24. Gemma Chan - Oscars, 2019

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Gemma Chan was delivering Barbiecore before it was even a thing. Chan wore a stunning statement parachute gown designed by Valentino at the 2019 Oscars. The dress allowed her to make a dramatic entrance that night and the ruffled collar is just the perfect finishing touch. 

25. Zendaya - The Greatest Showman Premiere, 2017

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Walking the carpet for The Greatest Showman premiere in 2017, Zendaya wore a breathtaking one-shouldered gown that was the embodiment of a monarch butterfly. The dress was designed by Moschino and featured a thigh-high split, which she paired with some simple strappy black heels. 

26. Lady Gaga - Grammys, 2011

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This look takes the cake when it comes to surprising red carpet looks. Known for her unique and sometimes downright creepy looks, Lady Gaga pulled out all the stops at the 2011 Grammy Awards. She didn't emerge from the egg, which was carried by a group of extra terrestrial-looking men, until her performance later that night where she was birthed from the prop on stage.  Truly a 'it has to be seen to be believed' look.

27. Beyonce - Superbowl, 2004

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A rather unusual outfit for a professional event, but smart casual attire was everywhere on the red carpet in the 2000s. At the Superbowl event in 2004, Beyonce wore a trusty pair of Uggs with a ruffled denim mini skirt and fitted tweed blazer. While it wasn't outrageous at the time, it's hard to imagine a celeb wearing a pair of UGGs to such a high-profile event now.

28. Madonna - MTV Video Music Awards, 1984

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When it comes to shocking avant-garde fashion looks, Madonna could teach a class in them. And her punky-bridal red carpet look at the MTV Video Music Awards in 1984 was proof of that.  She styled the Maripol dress with matching white lace gloves, layers of jewellery and of course her 'boy toy' metal belt. 

29. Zendaya - Met Gala, 2019

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Not only did Zendaya deliver one of the most out-there looks at the 2019 Met Gala, but she also gave an impressive performance with the help of her stylist-turned-fairy-godmother Law Roach. With a wave of Roach’s magic wand, the Cinderella-inspired Tommy Hilfiger dress lit up.  

30. Tracee Ellis Porter - Emmys, 2018

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Nothing quite makes a statement like bright pink and Tracee Ellis Ross’s gown at the 2018 did just that. The couture Valentino gown was a major fashion moment for the actress and one that may have just stolen the red-carpet fashion show that night. The dress was a dramatic fit and flare with statement billowing off-the-shoulder sleeves. 

31. Kim Kardashian - Met Gala, 2022

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This may be perhaps one of Kim Kardashian’s most controversial looks of all time as it outraged many fashion fans. The dress that she wore to the 2022 Met Gala was an archive piece that was originally worn by Marylin Monroe and had since been displayed at Ripley’s Believe it or Not Museum. Monroe wore the iconic Jean Louis gown during her historic birthday performance for JFK in 1962. The real controversy came when pictures were released revealing the damage caused to the gown after Kim had worn it.

32. Billy Porter - Oscars, 2019

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Walking the red carpet for the 2019 Oscars, Billy Porter wore a magnificent black tuxedo gown that exuded timeless class. The gown was designed by Christian Siriano and immediately generated media and internet buzz as people praised Porter’s refusal to dress according to gendered fashion norms. 

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