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In pictures: Iconic Oscars outfits that broke all the rules

In pictures: Iconic Oscars outfits that broke all the rules
By: Skynews.com Posted On: March 12, 2026 View: 15

In pictures: Iconic Oscars outfits that broke all the rules

The Oscars celebrate the craft and creative excellence behind the best movies of the year – but the red carpet ahead of the ceremony is quite a different matter.

It's about one thing only: Fashion.

The world's most famous catwalk, it has the power to take a celebrity's style moment and elevate it into historical popular culture.

So, as we get ready for the 2026 Academy Awards on Sunday, we're celebrating the red-carpet risk-takers and most memorable Oscar looks over the years.

Cher told designer Bob Mackie 'I don't want to look like a housewife in an evening gown'. Mission very much accomplished, I say. Pictured here with actor Don Ameche at the 1986 Oscars. Pic: Reuters
Image: Cher told designer Bob Mackie 'I don't want to look like a housewife in an evening gown'. Mission very much accomplished, I say. Pictured here with actor Don Ameche at the 1986 Oscars. Pic: Reuters
High low fashion at its best, Sharon Stone in a Vera Wang skirt and her husband's Gap shirt in 1998 Oscars. So iconic, Zendaya referenced it in her 2022 look (scroll down). Pic: Reuters
Image: High low fashion at its best, Sharon Stone in a Vera Wang skirt and her husband's Gap shirt in 1998 Oscars. So iconic, Zendaya referenced it in her 2022 look (scroll down). Pic: Reuters
Celine Dion's white John Galliano tuxedo, worn backwards, and with matching fedora was fashion surrealism at its best, causing plenty of double takes back in 1999. Pic: PA
Image: Celine Dion's white John Galliano tuxedo, worn backwards, and with matching fedora was fashion surrealism at its best, causing plenty of double takes back in 1999. Pic: PA
Could their have been anything more unexpected than Bjork's 2001 swan dress by Marjan Pejoski? It's remained in the pubic imagination for over a quarter of a decade and even has its own Wikipedia page. Pic: AP
Image: Could their have been anything more unexpected than Bjork's 2001 swan dress by Marjan Pejoski? It's remained in the pubic imagination for over a quarter of a decade and even has its own Wikipedia page. Pic: AP
Halle Berry made history in 2002 as the first black woman to win best actress, wearing a sheer Elie Saab dress. It was perfection. Pic: Reuters
Image: Halle Berry made history in 2002 as the first black woman to win best actress, wearing a sheer Elie Saab dress. It was perfection. Pic: Reuters
Gwyneth Paltrow's 2002 Alexander McQueen gown - with sheer top and full taffeta skirt - was brave, and divided the room. Pic: AP
Image: Gwyneth Paltrow's 2002 Alexander McQueen gown - with sheer top and full taffeta skirt - was brave, and divided the room. Pic: AP
Diane Keaton's 2004 Ralph Lauren creation was an homage to Annie Hall and her 1978 best actress win. Pic: PA
Image: Diane Keaton's 2004 Ralph Lauren creation was an homage to Annie Hall and her 1978 best actress win. Pic: PA
Never boring, always original. Prince in flares, heels, and his signature purple in 2005. Pic: Reuters
Image: Never boring, always original. Prince in flares, heels, and his signature purple in 2005. Pic: Reuters
The leg that launched a thousand memes, Angelina Jolie's black velvet Atelier Versace gown got plenty of Oscar attention in 2012. Pic: AP
Image: The leg that launched a thousand memes, Angelina Jolie's black velvet Atelier Versace gown got plenty of Oscar attention in 2012. Pic: AP
One of the most expensive garments in Academy Award history, valued at $4m, Jennifer Lawrence's voluminous Dior Haute Couture gown led to a trip, and a host of headlines in 2013. Pic: Reuters
Image: One of the most expensive garments in Academy Award history, valued at $4m, Jennifer Lawrence's voluminous Dior Haute Couture gown led to a trip, and a host of headlines in 2013. Pic: Reuters
Who says you need to wear trousers to the Oscars? Or socks for that matter. Pharrell Williams with wife Helen Lasichanh in 2014. Pic: Reuters
Image: Who says you need to wear trousers to the Oscars? Or socks for that matter. Pharrell Williams with wife Helen Lasichanh in 2014. Pic: Reuters
And why should women have all the fashion fun? Billy Porter wore a black velvet tuxedo dress in 2019, designed by Christian Siriano. Pic: Reuters
Image: And why should women have all the fashion fun? Billy Porter wore a black velvet tuxedo dress in 2019, designed by Christian Siriano. Pic: Reuters
Spike Lee wearing a gold and purple jacket in honour of late basketball player Kobe Bryant in 2020. Pictured with his wife Tonya Lewis Lee. Pic: AP
Image: Spike Lee wearing a gold and purple jacket in honour of late basketball player Kobe Bryant in 2020. Pictured with his wife Tonya Lewis Lee. Pic: AP
A punk-inspired Chanel suit for Kristen Stewart in 2022, redefining formal wear with short satin shorts and an unbuttoned white shirt. Pic: Reuters
Image: A punk-inspired Chanel suit for Kristen Stewart in 2022, redefining formal wear with short satin shorts and an unbuttoned white shirt. Pic: Reuters
Jada Pinkett Smith's Jean Paul Gaultier gown was a showstopper in 2022, ahead of her husband's literal showstopper later that evening. Pic: Reuters
Image: Jada Pinkett Smith's Jean Paul Gaultier gown was a showstopper in 2022, ahead of her husband's literal showstopper later that evening. Pic: Reuters
Zendaya's 2022 Valentino outfit echoed Sharon Stone's Vera Wang look 24 years earlier, but with an ab-revealing modern twist. Pic: Reuters
Image: Zendaya's 2022 Valentino outfit echoed Sharon Stone's Vera Wang look 24 years earlier, but with an ab-revealing modern twist. Pic: Reuters
Dwayne Johnson showing his softer side in peach satin with Emily Blunt at the 2023 Oscars. Pic: Reuters
Image: Dwayne Johnson showing his softer side in peach satin with Emily Blunt at the 2023 Oscars. Pic: Reuters
Malala Yousafzai stuns in a silver, sequined Ralph Lauren gown in 2023. Pic: Reuters
Image: Malala Yousafzai stuns in a silver, sequined Ralph Lauren gown in 2023. Pic: Reuters
As stunning from the back too. Pic: Reuters
Image: As stunning from the back too. Pic: Reuters
Re-defining maternity style, Rihanna wearing a bondage-inspired a custom dark brown Alaia ensemble to the Oscars in 2023. Pic: AP
Image: Re-defining maternity style, Rihanna wearing a bondage-inspired a custom dark brown Alaia ensemble to the Oscars in 2023. Pic: AP
Rihanna's look in full - it deserves it. Pic: AP
Image: Rihanna's look in full - it deserves it. Pic: AP
Somehow making pink and puffy work in 2024 - Ariana Grande. Pic: AP
Image: Somehow making pink and puffy work in 2024 - Ariana Grande. Pic: AP
Emboldened by her success, Grande went for pastels again the following year, but with a lampshade vibe. Pic: AP
Image: Emboldened by her success, Grande went for pastels again the following year, but with a lampshade vibe. Pic: AP
Emma Stone's mint Louis Vuitton gown was a hit in 2024 - but malfunctioned when Ryan Gosling performed I'm Just Ken. Let's face it, the dress never stood a chance. Pic: Reuters
Image: Emma Stone's mint Louis Vuitton gown was a hit in 2024 - but malfunctioned when Ryan Gosling performed I'm Just Ken. Let's face it, the dress never stood a chance. Pic: Reuters
Speaking of whom… Barbie star Ryan Gosling, bearing a little chest and a cheeky smile the same year. Pic: Reuters
Image: Speaking of whom… Barbie star Ryan Gosling, bearing a little chest and a cheeky smile the same year. Pic: Reuters
Composer Laura Karpman's 2024 outfit was described by commentators as 'glittering chaos'. She gave out chocolate bars from her sequined Dairy Milk bag. I, for one, am here for it. Pic. Reuters
Image: Composer Laura Karpman's 2024 outfit was described by commentators as 'glittering chaos'. She gave out chocolate bars from her sequined Dairy Milk bag. I, for one, am here for it. Pic. Reuters
Eugene Lee Yang, channelling Billy Porter's tuxedo dress five years earlier, this time in red, designed by Walter Mendez. Pic: AP
Image: Eugene Lee Yang, channelling Billy Porter's tuxedo dress five years earlier, this time in red, designed by Walter Mendez. Pic: AP
Da'Vine Joy Randolph in a beautiful sky-blue Louis Vuitton gown in 2024. Pic: Reuters
Image: Da'Vine Joy Randolph in a beautiful sky-blue Louis Vuitton gown in 2024. Pic: Reuters
Seventeen-time Oscar nominee Diane Warren wore a flame covered suit to celebrate her nod for song The Flame Inside in 2024. Pic: AP
Image: Seventeen-time Oscar nominee Diane Warren wore a flame covered suit to celebrate her nod for song The Flame Inside in 2024. Pic: AP
Andrea Riseborough in a Loewe plaid tartan dress in 2024, the year after her surprise nomination caused quite a stir. Pic: AP
Image: Andrea Riseborough in a Loewe plaid tartan dress in 2024, the year after her surprise nomination caused quite a stir. Pic: AP
Colman Domingo, always the most stylish man on any red carpet, wearing a double-breasted, rose-red tuxedo from Valentino in 2025. Pic: AP
Image: Colman Domingo, always the most stylish man on any red carpet, wearing a double-breasted, rose-red tuxedo from Valentino in 2025. Pic: AP
Never afraid to stand out, Jeff Goldblum in a Prada outfit with a lilac scarf in 2025. Pic: Reuters
Image: Never afraid to stand out, Jeff Goldblum in a Prada outfit with a lilac scarf in 2025. Pic: Reuters
Whoopi Goldberg in an off-the-shoulder blue 'liquid water' organza gown by Christian Siriano in 2025, giving fans a peak of her rarely seen shoulder tattoo (a colourful dragon, in case you're wondering). Pic: AP
Image: Whoopi Goldberg in an off-the-shoulder blue 'liquid water' organza gown by Christian Siriano in 2025, giving fans a peak of her rarely seen shoulder tattoo (a colourful dragon, in case you're wondering). Pic: AP
A bright 'butter yellow' Givenchy suit for Timothee Chalamet in 2025, with matching silk shirt, a Cartier diamond choker, and black boots. Pic: Reuters
Image: A bright 'butter yellow' Givenchy suit for Timothee Chalamet in 2025, with matching silk shirt, a Cartier diamond choker, and black boots. Pic: Reuters
Cynthia Erivo in an emerald-green Louis Vuitton gown and a customised Wizard of Oz-themed nail set in gold and green in 2025. Absolutely Wicked. Pic: Reuters
Image: Cynthia Erivo in an emerald-green Louis Vuitton gown and a customised Wizard of Oz-themed nail set in gold and green in 2025. Absolutely Wicked. Pic: Reuters

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