The Oscars is the grand finale of awards season, and for many stars, they will save their best look for last. But what constitutes a memorable red carpet ensemble isn’t always the most impeccably or tastefully styled. Sometimes it’s layered with meaning, or joyfully bonkers, or a wardrobe malfunction that somehow went right... Scroll on to see the looks that went down in Academy Awards history.
Taking the plunge: Liz Taylor in Edith Head, 1970
What to wear when you are one half of the world’s most glamorous couple and your career is rather on the wane? Liz Taylor chose a plunging periwinkle chiffon dress, which famously matched her violet eyes and revealed the mother of all décolletés. Created by the costume designer Edith Head, it not only showed off her more-than-ample cleavage but also a 69-carat pear-shaped diamond that Richard Burton bought for her, originally as a ring from Cartier for a rumoured $1.1m. After their second divorce, Taylor sold the diamond in 1978 for £5m, part of which was used to build a hospital in Botswana. As for the dress? Mattel reportedly paid $167,500 for it at a charity auction.
Cher-raising: Cher in Bob Mackie, 1986
This black, beaded two-piece (complete with a 2ft-high rooster-feather headdress) by Bob Mackie was way ahead of its time. Never mind the fact that she resembled an ostrich who had just discovered S&M, Cher was actually only paving the way for Rihanna and Lady Gaga in the “more is more” stakes. Two years later, she was at it again, in an outfit that would be a precursor to the Noughties sheer trend. It offered coverage yet still showed off a silhouette honed by thrice-weekly barrecore sessions. Whether revealing all or steathily covering up, Cher certainly staked her claim to Oscar fashion history.
Basically brilliant: Sharon Stone in Gap and Vera Wang, 1998
Nearly two decades before normcore hit, Sharon Stone took a white Gap shirt (cooler still, it belonged to her husband, Phil Bronstein), teamed it with a Vera Wang skirt – and wore it down the red carpet. The start of high-low occasion wear? Possibly. But Stone was also on to something. “Stone wears Gap to the Oscars,” screamed the headlines, proving that less often leads to more. The sexiest woman in Hollywood proved that she didn’t need to diet into a sparkling princess dress or reveal everything to turn heads (admittedly, she’d already done that in Basic Instinct). These days, even the sisters behind Rodarte, champions of millefeuille layers of tulle, admit that a pair of jeans feels the most modern look at a black-tie do. We have to agree – spectacular looks can be comfy, too.
Tears in a gown: Gwyneth Paltrow in Ralph Lauren, 1999
Some thought it was perfectly befitting of a new star nominated for her first Oscar (for Shakespeare in Love). A classic, full-skirted, spaghetti strap, bubblegum-pink taffeta princess gown designed for the all-American girl by the all-American designer Ralph Lauren, it made Time magazine’s list of the greatest Oscar dresses of all time. Others described it as a prom dress, and criticised the fit and her choice of scraped-back hair. Either way, it was upstaged by the actress herself when she got up to make one of the most tearful acceptance speeches in Oscar history – and began sobbing before she even left her seat.
Swanning around: Björk in Marjan Pejoski, 2001
When fashion historians come to plunder the Oscar fashion annals, Björk’s swan dress, designed by Macedonian-born Marjan Pejoski, will go down as one of the most talked-about – adored and reviled in equal measure. It has been the highlight of a MoMA retrospective honouring the Icelandic musician’s work and was even reimagined by Valentino for its spring/summer 2014 couture collection. What’s often forgotten is that Björk brought six ostrich eggs with her, lifting up the feathers of her dress to “lay” them on the red carpet. As she later revealed: “Other people’s bodyguards kept picking them up and saying, ‘’Scuse me, ma’am, you dropped this.’”
Sheer talent: Halle Berry in Elie Saab, 2002
Still the only black woman to have won a best actress Oscar (for Monster’s Ball), Halle Berry chose a showstopping dress that lived up to that history-making night. There was nothing expected about it: the burgundy silk skirt was made in two parts, with a narrow column surrounded by a floor-sweeping train, while its Lebanese designer, Elie Saab, added extra flowers to the embroidered mesh bodice at Halle’s request to make it a touch more demure. And given how many column inches she – and the dress – generated that night, and for years to come, that wasn’t a bad idea at all.
‘This old thing?’: Reese Witherspoon in vintage Christian Dior, 2006
Some years, neutral minimalism dominate the Oscars, while other years it’s the billowing swish, swish of ultra-feminine fishtail gowns. Back in 2006, resembling your six-year-old niece in a party dress was just fine as long as you could call your outfit “vintage”. This was five years after Julia Roberts accepted her award in a decade-old monochrome Valentino dress and Renée Zellweger wore a 1950s yellow chiffon concoction by Jean Desses. Reese Witherspoon found her 1955 Christian Dior gown in a Paris boutique but had trouble convincing the owner to part with it as it had once belonged to royalty. Vintage was one way of showing your fashion savvy in the Noughties, even if most of what we mere mortals wore was little more than elevated charity-shop chic.
Fallen beauty: Jennifer Lawrence in Dior, 2013
Lawrence’s fall when approaching the stage to collect her Academy Award for best actress was so charming, some wondered whether it was intentional. The dress, a Dior haute couture creation by then artistic director Raf Simons, played a key role – it somehow looked even more beautiful mid-tumble, with the skirt cascading across the steps. Then there was the jewellery: the diamond Chopard necklace that had been draped down her back, fell across her shoulders. It’s proof that fashion only really comes alive when you break free from the static red carpet pose – and Lawrence ensured that her look went down in history.
The $18m showstopper: Cate Blanchett in Armani Privé and Chopard, 2014
Even by couture standards, the outfit that Cate Blanchett chose the year she won best actress for Blue Jasmine was extravagant. The tiered Armani Privé gown, made from 25 metres of nude tulle and embellished with thousands of dégradé sequins, was reportedly worth $100,000 and took about 600 hours to make (and weighed a ton, as Cate revealed on the red carpet). But it was the jewellery that made jaws drop: approximately $18m-worth, in the form of a brown diamond bracelet, a pear-shaped diamond ring and earrings encrusted with 62 opals, all by Chopard.
Out of the blue: Lupita Nyong’o in Prada, 2014
Lupita’s management team staged one of the most strategic red carpet assaults in history, culminating in this breathtaking gown – its impact all the greater among the sea of muted shades that year. Known solely at that point for her role in 12 Years a Slave, Lupita’s chameleonic, colourful style was engineered to prove she was capable of anything – and be a strong female lead. No surprises that Lupita went on to win the Oscar and a Lancôme contract, which, as Isabella Rossellini once said, was like “winning the lottery” because it allowed her to take only roles she wanted to. Designed by Prada, the silk dress’s pale blue was a nod to Kenya, where the actress was raised, while the neckline echoed that of Liz Taylor, whose style she admires.
Hand-made heaven: Julianne Moore in Chanel couture, 2015
Having stormed the awards season, picking up gongs left, right and centre for Still Alice, Julianne Moore might have had a hunch that she was in with a very good chance of winning the best actress award. So, very sensibly, she turned to Chanel couture. Her monochrome strapless gown was apparently designed by Karl Lagerfeld himself; it was lined with silk crêpe and featured a best-supporting concealed bustier. According to Chanel, it featured 800,000 hand-painted resin sequins and flowers made from ivory, beige and black organza and tulle. The dress took 27 workers 987 hours – around six weeks – to create. Yes, really!
One for the boys: Billy Porter in Christian Siriano, 2019
Who said gowns were just for women? When multi-hyphenate star Billy Porter stepped out in a Christian Siriano tuxedo gown, he shook up our expectations of who should wear what on the red carpet. It paved the way for male celebrities to be more creative with menswear, a ripple effect that continues to be felt today in the red carpet looks of Jacob Elordi, Timothée Chalamet and Oscar Isaac. Porter told Vogue at the time: “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.”
The one with a message: Natalie Portman in Dior, 2020
The 2020 Oscars nominations were controversial for their lack of women and people of colour. Natalie Portman, who wore a black and gold gown for the occasion, chose to honour the women snubbed by the Academy by having their names embroidered onto the edge of her cape. A tasteful yet powerful way to convey an important message.
The one with the trainers: Chloé Zhao in Hermès, 2021
The pandemic lockdowns changed our relationship with clothes, and nowhere was this more apparent than in Chloé Zhao’s look for the Oscars in 2021. The director, who was named best director for Nomadland (the first woman of colour and second woman ever to win the award), wore a knitted Hermès dress with box-fresh white trainers on the red carpet. With her hair styled in two braids and minimal make-up, she was ahead of the curve on quiet luxury, and offered incontrovertible proof that you don’t need to sacrifice comfort for style. That, and trainers can and should be welcome on even the most formal red carpet.
The 1951 recreation: Carey Mulligan in Balenciaga, 2024
There’s vintage, there’s archive, and then there’s the rare antique, which nobody (bar Kim Kardashian) would actually wear on the red carpet for fear of damaging it. Carey Mulligan did the next best thing in 2024, when she wore a recreation of a 1951 Balenciaga couture gown – the first time the house has remade a dress from its archives for the red carpet. The strapless design was fitted through the body, with a scalloped hem and full, white, tulle skirt. The look was completed by inky black opera gloves. “I think it’s my favourite dress I’ve ever worn,” Mulligan told Vogue. “It’s the most incredible shape and so classic, but feels really modern.”
The broken zip: Emma Stone in Louis Vuitton, 2024
Better known as the dress with the broken zip. Emma Stone’s pale green peplum-waisted dress was a custom Louis Vuitton creation (the actress has long been an ambassador for the house) and a red carpet showstopper. The wardrobe malfunction occurred just before Stone was announced as best actress for her role in Poor Things. When she reached the mic to collect her award, she said: “Oh boy, my dress is broken. I think it happened during ‘I’m Just Ken’. I’m pretty sure.” Stone was quickly “sewed back in” afterwards, so that she could celebrate her win unhindered.
The chandelier: Ariana Grande in Schiaparelli, 2025
If we were still socially distancing, Ariana Grande’s dress for the 2025 Oscars would have been ideal. The Schiaparelli creation featured a wide tutu-like peplum with a waved hem, and a tulle skirt embellished with crystals. It concluded her run of “method dressing” as her Wicked character, Glinda, on the red carpet. A sensational grand finale.