Art of Style

11 of the best Oscar looks of all time


If there’s a greater joy at this time of year than scrolling through red-carpet pictures the morning after the Oscars, then we’ve yet to find it. The anticipation is great, which is why, as we wait for this year’s crop of dresses to be unveiled, our fashion team has been trawling through past favorites. Here are our highlights – what are yours?

Greta Gerwig wears Rodarte, 2018
“As 2018’s only female director nominee, all eyes were on Greta Gerwig. Far from conforming to how a woman in a male-dominated world might be expected to dress, her embroidered, sunflower-yellow Rodarte gown was more in sync with the Ladybird director’s brilliant vision than clichéd dress codes. Renowned for her whimsical red-carpet style, she’s stayed true to her love of fearless and ultra-feminine fashion: this dress was optimistic, beautiful and so much more, perfectly symbolic of what Gerwig brings to the film industry.” Gillian Brett, Fashion Features Associate
Cate Blanchett wears Givenchy Couture by Riccardo Tisci, 2011
“I love how this dress is soft and fierce at the same time; it feels so relevant again for the SS18 season. Yes to pastels, but in a modern, grown-up way.” Anina Heé, Associate Shopping Editor
Martha Plimpton wears vintage, 1989
“Designer Erdem Moralioglu recently reminded me of this outstanding Oscars dress as it is his all-time favorite red-carpet moment and, thanks to him, it’s now also mine. Martha Plimpton on the arm of River Phoenix in a 1930s vintage dress was the total antithesis to the high-octane glam of the time (this was the same year that Melanie Griffith wore a huge white meringue bridal gown and pearls). If any actress replicated this in 2018, they would still look more modern than anyone else on the carpet.” Kay Barron, Fashion Features Director
Farrah Fawcett wears Stephen Burrows, 1978
“Farrah Fawcett is the epitome of ’70s glam and this slinky gold disco-chic gown by Stephen Burrows is her perfect red-carpet partner. The dress is daring but simple, especially paired with no jewelry and her trademark ‘Farrah flick’.” Marquessa Lucas-Box, Fashion Assistant
Naomie Harris wears Calvin Klein by Appointment, 2017
“It takes a lot of confidence to bare your ankles at the Oscars, but this makes me wonder why more people don’t do it. The dress feels so effortless; a simple shape, a fleeting cutout and, when you get up close, you find it’s covered in sequins, too. And then she’s paired it with asymmetric shoes to finish – a pretty directional flourish when you consider how traditional most Oscars looks are. It was a genuine fashion moment: the first red-carpet look by Calvin Klein under the direction of Raf Simons who had unveiled his first collection for the label a few weeks before. Red-carpet perfection.” Emma Sells, Fashion Features Editor
Michelle Williams wears Vera Wang, 2006
“You don’t see a lot of yellow on red carpets, which, largely, is a good call. Even more so since 2006, because every canary-colored dress worn to an awards ceremony will forever be compared to this, and it is hard to think that anything could ever surpass it. How do you choose an event dress when you are one of the coolest actresses in the world? Because, generally speaking, glamorous gowns are not cool. Beautiful, yes; daring, sometimes; but rarely cool. In truth, Vera Wang would not be the first designer who popped into your mind. But it’s the many elements of surprise that make this so perfect. Wang + Williams; pleats + gathers; vintage shaping + modern actress; custard yellow + that scarlet lip... A masterclass in how to do you, no matter what the dress code.” Jennifer Dickinson, Digital Editorial Director
Lauren Hutton wears Halston, 1975
“I love how effortless and feminine Hutton looks in this simple, banded, plunging, Greek-goddess style dress. And that she has pared it back with natural hair and makeup and no jewelry, making it all about her.” Morgan Pilcher, Fashion Editor
Lupita Nyong’o wears Prada, 2014
“Simplicity is always more powerful. Lupita Nyong’o’s custom-made Prada dress almost vibrated in its purity of color and clean A-lines. The movement of the pleating borrowed from vintage costume designers, and the color reminded Nyong’o of her hometown of Nairobi. It was the perfect way to mark her arrival in Hollywood, winning the Best Supporting Actress award for 12 Years a Slave.” Emily Zak, Executive Fashion Editor
Nicole Kidman wears Dior, 1997
“Nicole Kidman’s silk Dior gown, designed by John Galliano, embroidered with chinoiseries and featuring side slits, is my landmark awards-season moment. I love the unusual color, but also the vintage feel and the fact that Galliano made a dress so perfect for her body. He had just been appointed creative director of Dior and this appearance signaled his arrival as a new force on the red carpet. Equally, it earmarked Kidman as an experimental fashion darling.” Marian Nachmia, Senior Fashion Assistant
Jane Fonda wears Yves Saint Laurent Couture, 1972
“I love the pants suit Jane Fonda wore in 1972 while accepting an Oscar for her role in Klute. ‘I bought this Yves Saint Laurent suit right after I gave birth to my daughter in 1968,’ the actress has said. ‘I decided to wear it to the Oscars when I won for Klute because I felt it suited the somber times. Besides, I wasn’t into buying fancy dresses when the Vietnam War was still being fought.’” Gabriele Hackworthy, Global Editorial Fashion Director
Ruth Negga wears Valentino, 2017
“Ruth Negga’s love affair with Valentino reminds me of the golden era of Hollywood glamour. Wearing this beautiful, custom-designed scarlet dress to the 2017 Oscars – when she was nominated for Loving, the true story of a couple who were banished from Virginia for their interracial marriage – she confidently and elegantly asserted her place among Hollywood’s most talented actors. She’s a force to be reckoned with on-screen and on the red carpet.” Gillian Brett, Fashion Features Associate

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