The best Oscars red carpet looks of all time

From Sharon Stone's iconic look to Bjork's memorable swan dress, here are the best outfits from the Oscars red carpet

A composite image of some of the best Oscars red carpet looks of all time, featuring Cher, Zendaya and Daryl Hannah.
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While it's not the only red carpet in showbiz, the Academy Award stage is always a top choice for celebrities to don their most show-stopping outfits.

It's the biggest night in filmmaking each year, so it's no surprise that stars often choose to wear outrageous or decadent looks for the Oscars red carpet. Though the fashion has changed over the years, the looks always impress, from now-iconic designer dresses to more unique choices. We break down our favourites below, from Sharon Stone's iconic look to Bjork's memorable swan dress.

The best Oscars red carpet looks of all time

Zendaya in 2022

Zendaya.

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When Zendaya walks a red carpet, we know it'll be in an incredible outfit and her 2022 Oscars look did not disappoint. In an homage to Sharon Stone's iconic white shirt in 1998, Zendaya wore an ultra-cropped silk shirt with a silver sequinned skirt, both from Valentino. Her messy updo also invoked the 90s.

Sarah Jessica Parker in 1995

Sarah Jessica Parker.

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Sarah Jessica Parker's best looks prove that she's just as stylish - if not more - than her character Carrie Bradshaw and this LBD for the 1995 Oscars is 90s through and through. The fitted, strapless dress is the perfect understated look for the ceremony and is zhuzhed up by the actress's signature voluminous curls.

Grace Kelly in 1955

Grace Kelly.

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Grace Kelly was known for her impeccable style and timeless fashion sense and her clothing choices have inspired designers and fashion lovers for decades, influencing Mad Men costume designers as well as later stars Billie Eilish and Elle Fanning. Her mint green dress, designed by Edith Head, and satin gloves would become one of her most iconic looks, worn on the night of her first Oscar win in 1955.

Elizabeth Taylor in 1960

Elizabeth Taylor.

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Elizabeth Taylor wore some incredible dresses for awards ceremonies - her dress from the year after, where she won her first Oscar, is more often cited as her best - but this lace look is our absolute favourite. The embellished flowers and extra panels on the bodice are quite progressive for the fashion in 1960, even though the gown has a bridal feel.

Cher in 1988

Cher.

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On the night she took home a Best Actress Academy Award for her role in Moonstruck, Cher wore a Bob Mackie dress adorned with sparkly sequins. Her accessories perfectly matched the dress, with ultra-long black earrings, an elaborate updo and an elegant stole.

Gwyneth Paltrow in 1999

Gwyneth Paltrow.

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At just 26 years old, Gwyneth Paltrow won a Best Actress gong and gave one of the best Oscars speeches, but the moment is also well-known for her stunning dress. Supposedly, Paltrow didn't work with a stylist for this look and simply picked up the baby pink gown from Ralph Lauren a few days before the ceremony.

Bjork in 2001

Bjork.

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The 'swan dress' is so infamous that there's a whole Wikipedia page dedicated to it. Donning the dress, designed by Marjan Pejoski, at the 2001 Oscars, Icelandic singer Björk stated that she wore the outfit knowing it would probably be her first and only time at the awards ceremony. The outfit was widely mocked and criticised, to which Björk responded "It's just a dress".

Trey Parker and Matt Stone in 2000

Trey Parker and Matt Stone.

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Trey Parker and Matt Stone, the creators of the TV show South Park, turned up to the Oscars red carpet in 1999 in shocking but tongue-in-cheek outfits. While Trey parodied J Lo's iconic green Versace dress - which was literally responsible for the creation of Google Images - Matt opted for a recreation of Gwyneth Paltrow's 1990 Ralph Lauren gown. It's safe to say that heads were turned.

Halle Berry in 2002

Halle Berry.

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Halle Berry was the first Black woman to win the Best Actress Oscar and her emotional acceptance speech went down in history as one of the most important Academy Award moments. Berry's gorgeous Elie Saab dress, which featured a sheer bodice and a taffeta skirt, is now on display at the Academy Museum of Motion Pictures.

Cate Blanchett in 2005

Cate Blanchett.

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Cate Blanchett has given us several incredible Oscars outfits, but this yellow gown is probably one of our favourites. The silk taffeta Valentino dress regularly topped lists of the best Oscars looks of all time following its appearance at the 2005 Oscars. Of the gown, Blanchett said: "When I tried it on, the sun was beaming through the windows, and the fabric was shot through with a pink and blue. Because the Oscars start out as a daytime event, I thought it would be amazing in the sunlight".

Jennifer Aniston in 2006

Jennifer Aniston.

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Sometimes the simple outfits are indeed the best. In the 90s, Jennifer Aniston's best looks often consisted of laid-back and grungy pieces, but this black scoop-neck Rochas gown from 2006 offered a more sophisticated yet subtle take on the red carpet trends of the time. 

Jennifer Lawrence in 2013

Jennifer Lawrence.

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Jennifer Lawrence's appearance at the 2013 Oscars is more often associated with events other than the dress she wore: her win making her the second-youngest winner in the category, her stumble while walking up to the stage, her admission to the press that she "did a shot" before being interviewed. But while her fall made for one of the most memorable Oscars moments, Lawrence's strapless Dior gown deserves attention, too. The stunning dress is thought to be the most expensive one designed for the Oscars and is worth around $4 million.

Gemma Chan in 2019

Gemma Chan.

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Gemma Chan walked the Oscars red carpet in 2019 in a gorgeous, Barbie pink ruffled Valentino gown. From the bubblegum shade to the extravagant ruffled collar - and the pockets! - this is one of our favourite looks of all time.

Audrey Hepburn in 1954

Audrey Hepburn.

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Often thought of as one of the most stylish and classy women to have ever lived, it's no surprise Audrey Hepburn would turn up to the Oscars in a beautiful, timeless look. The white floral dress was the result of Hepburn meeting with Givenchy, who actually thought he was going to be meeting with fellow actress (of no relation) Katharine Hepburn. Luckily, the meeting was fruitful and Givenchy went on to design not only this iconic Oscars look but the famous LBD worn by Audrey in Breakfast in Tiffany's.

Cher in 1973

Cher in 1973.

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Cher's looks throughout the 70s were always iconic, but this midriff-baring two-piece is probably one of her most well-known 'fits. Designed by her friend Bob Mackie, the sequinned look was fairly controversial for the time, but Cher's ability to make literally anything look good means that it went down in history as one of her best fashion choices.

Barbra Streisand in 1969

Barbra Streisand.

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The 1969 Oscars were a memorable night for several reasons; one being that it was the first (and still only) time that two actresses were tied for the Best Actress award, Barbra Streisand and Katharine Hepburn. Another is the outfit Streisand opted for - a sheer, sparkling pantsuit by Arnold Scaasi, which featured flared trousers, a white collar adorned with a black bow, and white tuxedo cuffs. Though Streisand later claimed she was horrified to learn how see-through the pantsuit really was, the outfit was immediately controversial, a bold but brave fashion choice from the esteemed star.

Lauren Hutton in 1975

Lauren Hutton.

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In an era where celebrities didn't have stylists and mostly dressed themselves, Lauren Hutton's 70s gown, soft makeup and seemingly unstyled hair prove that the actress was capable of pulling off an incredible look without much help. The low-cut, rainbow chiffon dress is pure 70s but has transcended fashion trends and styles since, seeing a resurgence in popularity on social media in recent years.

Sharon Stone in 1998

Sharon Stone.

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It's a word that's bandied around a lot, but Sharon Stone's 1998 'fit at the Oscars is truly one of the most iconic red carpet moments of all time. While celebrities are known to walk the carpet nowadays in much more 'risky' looks, in 1998, Sharon's decision to pair an unbuttoned, oversized white shirt - from Gap, no less - with a floor-length satin Vera Wang skirt was completely boundary-pushing. It's one of our favourite looks, full stop, and it's rightly cemented legendary status in fashion history.

Reese Witherspoon in 2006

Reese Witherspoon.

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Winning Best Actress for her role in the Johnny Cash biopic Walk the Line, Reese Witherspoon wore a show-stopping vintage Dior dress. The actress later said it was her favourite look she's ever worn, telling her followers: "It was a 1957 Christian Dior bought at a vintage store in Paris. So dreamy!"

Michelle Williams in 2006

Michelle Williams.

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Michelle Williams' saffron-coloured Vera Wang gown in 2006 went down in history as a top-tier Academy Award 'fit. While yellow isn't always the most popular choice for the red carpet, Michelle pulls it off perfectly, aided by the low-maintenance bun with wispy bangs.

Sandra Bullock in 1997

Sandra Bullock.

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While it's not her most famous Oscars look, we love the simplicity of this Richard Tyler dress, worn by Sandra Bullock in 1997. From the thin straps and slip dress vibe to the muted brown shade, this look is pure 90s, and the noticeable blush, blue eyeshadow and reddish-brown lip also make this one of our favourite 90s makeup looks.

Lupita Nyong'o in 2014

Lupita Nyong'o.

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At the beginning of her career, Lupita Nyong'o attended the Oscars for the first time and ended up winning a Best Supporting Actress gong for her star turn in 12 Years a Slave. Reportedly, both Stella McCartney and Alexander McQueen reached out to Nyong'o to offer their designer services for the big night, but she went with Prada instead; her gorgeous blue gown is widely considered to be one of the best Oscars looks to ever grace the red carpet.

Cate Blanchett in 1999

Cate Blanchett.

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In a dress that would fit perfectly into the naked dress trend of later years, Cate Blanchett looked incredible in this revealing look. The John Galliano gown from the 1999 Oscars combined sparkly floral adornments on a sheer back, with an equally sheer front section, which she matched with some chic satin heels.

Florence Pugh in 2024

Florence Pugh.

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Little Women star Florence Pugh hasn't always hit the mark with her red-carpet outfits, with some of her dresses even stirring controversy. Pugh's 2024 Oscars look featured a structured peplum bodice (complete with 'floating straps), as well as a satin silver skirt, with both partly adorned with water-like shiny beads. Gorgeous.

Daryl Hannah in 1990

Daryl Hannah.

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Have you ever seen a more 90s red carpet look? The sunglasses, the sheer (fingerless) gloves, the flowing curls; we're obsessed with every part of Daryl Hannah's 1990 Oscars 'fit. The mermaid cut of Hannah's gold dress is particularly apt, considering she played a mermaid in the 1984 film Splash.

Zendaya in 2021

Zendaya.

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Zendaya's professional partnership with stylist Law Roach is one of the best decisions the star has ever made, and this bright yellow dress with matching platform heels is one of our favourite looks. It's one of those dresses that could only look this good on someone as chic as Zendaya - the colour isn't exactly subtle, but it looks incredible on her. The actress kept her hair long, wavy and simple to keep the focus on her dress and the chunky silver necklaces.

Kate Winslet in 1996

Kate Winslet.

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In 1996, the same year Kate Winslet's most well-known film, Titanic, was released, the 21-year-old turned up to the Oscars (for which she was nominated, for the first time, for her role in Sense and Sensibility), in style. Her dress of choice, a gorgeous pink Vivienne Westwood number, predicted the Barbiecore trend by about 27 years.

Madonna in 1991

Madonna.

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One of Madonna's best looks of all time, this Bob Mackie dress, fur stole and all the accessories - long gloves, blonde pin curls, red lipstick - is pure Old Hollywood, with Hollywood icon Marilyn Monroe coming to mind in particular. Madonna was the perfect person to pull this look off.

Michelle Yeoh in 2019

Michelle Yeoh.

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Michelle Yeoh has been wowing with her Oscars dresses for the last few years, but her 2019 sequinned look is without a doubt our favourite. The Elie Saab Haute Couture gown featured an off-the-shoulder, fitted sparkling bodice, with a beautifully embellished tulle skirt - and the accompanying accessories are the perfect match.

Cate Blanchett in 2000

Cate Blanchett.

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This slinky black dress with gold detailing reminds us slightly of Elizabeth Hurley's iconic Versace 'safety pin dress', but is still utterly unique. The Jean Paul Gaultier gown was worn by Cate Blanchett at the 2000 Oscars ceremony, paired with a simple up-do in order to keep all the attention on the backless dress.

Saoirse Ronan in 2020

Saoirse Ronan.

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Saoirse Ronan always has impeccable style, and the 2020 Oscars red carpet proved this. Her custom Gucci gown featured a plunging neckline and a lavender skirt, and while the outfit stood out on its own for being gorgeous, it turns out that the black bodice of the gown was actually upcycled from the dress Ronan wore the previous weekend to the BAFTAs.

Geena Davis in 1992

Geena Davis.

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Three years after winning the Best Supporting Actress gong for her role in The Accidental Tourist, Geena Davis showed up in this incredible and unique gown, designed by Ruth Meyers and Bill Hargate. Blending 80s prom aesthetics with Old Hollywood glamour, this bold look may have featured on some 'worst-dressed' lists, but it's still one of our favourites.

Hannah Holway
Shopping writer

Hannah is the UK Shopping Writer for woman&home. As a shopping writer, Hannah has written on everything from period pants to wine subscriptions, and is especially interested in sustainable alternatives to well-known products, as well as books and homeware accessories. 

Before she joined the team at woman&home Hannah headed up the social media accounts for Wonderland in 2019, where she was also a Contributing Editor for the magazine’s sister titles. During the COVID-19 pandemic, Hannah also explored evolving shopping trends at New York Magazine’s The Strategist UK, researching everything from face masks to status candles and even pens.