The 20 Best Oscars Looks From the Last 20 Years

Two decades of the world’s most anticipated red carpet event distilled down to the very best looks

Words by ALISON EDMOND, executive creative and fashion director


Oscar dresses are as divisive to fashionistas as football teams are to NFL fans. I have been obsessed with watching the Academy Awards since I was in my late teens, when I religiously stayed up until the wee hours in London with my oldest friend year after year to celebrate Los Angeles’ biggest night. And of course, half the fun — perhaps even three-quarters — was seeing the red carpet choices the stars had made. Whether we were critiquing, marveling, loving or hating, the fashion was essential viewing. Global fascination with sartorial hits and misses has only increased since social media has grown to own public opinion, and designers and stylists have become more and more involved in this competitive game.

In celebration of the 2020 Academy Awards, we’re presenting the 20 best looks from the past 20 Oscars — in my humble opinion — and it’s these particular looks that have left such a lasting impression on my psyche.


1. Zoë Saldana in Givenchy Haute Couture (2010) — presenter
This Riccardo Tisci-designed confection-like gown was shockingly beautiful in its craftsmanship and cut, and carried off by the uber-elegant Zoë Saldana to absolute perfection. While this would have been too much on most mere mortals, her dancer’s frame and perfect poise make this my all-time standout Oscars look.

2. Gwyneth Paltrow in Tom Ford (2012) — presenter
Here was the ultimate lesson in minimal chic. A masterpiece from Tom Ford, this look has been imitated numerous times but never looked so good as on Ms, Goop herself.


3. Lupita Nyong’o in Calvin Klein (2015) — presenter
Seamstresses hand-sewed over 6,000 natural pearls onto this incredible custom gown by designer Francisco Costa for Calvin Klein, worn by Lupito Nyong’o the year after her triumphant Best Supporting Actress win for 12 Years a Slave, as she went on to become a perennial red carpet favorite. Famously stolen from her hotel after the ceremony, the dress was eventually returned.

4. Cate Blanchett in Givenchy Haute Couture (2011) — presenter
Blanchett has a personal style that always kills on the red carpet, and she is one of the few who can make a fashion-forward couture gown look like her own. This pale lilac halter gown with a beaded placket by Riccardo Tisci was one of their many successful partnerships in chic.

5. Tilda Swinton in Lanvin (2008) — winner, Best Supporting Actress, Michael Clayton
Always a winner in unique style, Tilda Swinton killed it in this dramatic diaphanous black velvet sheath by Alber Elbaz during his heyday at Lanvin. She also dyed her hair scarlet and showed us that classic dress code rules can be broken beautifully.


6. Marion Cotillard in Jean Paul Gaultier Haute Couture (2008) — winner, Best Actress, La Vie En Rose
Celebrating the best of her native France, Cotillard chose this amazing mermaid look with delicately embroidered “scales” and a fishtail train by the Gallic fashion hero Jean Paul Gaultier. She wowed at the 80th Academy Awards with both her onscreen performance as Edith Piaf and on the red carpet with her avant-garde French style.

7. Uma Thurman in Christian Lacroix Haute Couture (2004) — presenter
It may have been a controversial choice that was universally panned, but I personally loved this Lacroix look. Having just attended the label’s decadent couture show in Paris, it was a dream to see the look come to life on the gorgeous Uma Thurman, and I will always commend tasteful bravery. Fashion-forward choices are not always appreciated in the moment, as they are, indeed, ahead of their time.


8. Alicia Vikander in Louis Vuitton (2016) — winner, Best Supporting Actress, The Danish Girl
Alicia Vikander was a breath of fresh air on the 2016 red carpet, with her pale-lemon puffball gown with flashes of silver sequins, designed by Nicholas Ghesquiere, whose pieces she continues to wear regularly. Romantic and cool at the same time, it was a modern classic reimagined.

9. Naomie Harris in Calvin Klein (2017) — nominee, Best Supporting Actress, Moonlight
I loved this risqué sequined look by Raf Simons. Its short length made it a risky choice, but Naomie Harris’ fabulous legs and asymmetric shoes, plus the drama of the long train, made it worthy of the Oscars red carpet and a surefire hit.

10. Amy Adams in Oscar de la Renta (2013) — nominee, Best Supporting Actress, The Master
Sometimes the classic silhouettes just wow us, and this powder blue Oscar de la Renta fairy-tale moment was flawless on the uber-talented Amy Adams. Inspired by a vintage photo, the frothy tulle train was all hand-pulled tiers, with a hand-beaded bodice.


11. Zoë Saldana in Alexis Mabille Couture (2013) — presenter
The effortlessly chic Zoë Saldana nailed it (once again) in this unconventional monochrome bustier gown with floral applique, designed by French couturier Alexis Mabille. I have yet to see her put a foot wrong on the red carpet.

12. Hilary Swank in Guy Laroche (2005) — winner, Best Actress, Million Dollar Baby
This navy blue backless dress was a mastery in drape and construction by Herve Leroux at Guy Laroche, and it showed off Swank’s extraordinary physique to its very best. A modernist choice in a sea of predictable strapless gowns that year, it was apparently a superstitious last-minute choice, repeating the scenario of her eleventh-hour dress switch at the Oscars in 2000, where she also won the Best Actress accolade.


13. Jennifer Lopez in Tom Ford (2019) — presenter
This silver dynamo of a dress illustrated Tom Ford doing what he does best. A futuristic, form-fitting look with intricate mosaic mirrored detail, it transformed Jennifer Lopez into a modern-day siren, fully covered but still sexy as hell.

14. Penélope Cruz in Chanel Haute Couture (2008) — presenter
Cruz has the charisma of an old-school Hollywood star, and she channels that in all her red carpet picks. This corseted black feathered Chanel gown was the ultimate in vintage style. Had it not been 2008, it could easily have been 1958.

15. Zendaya in Giambattista Valli Couture (2018) — presenter
The combination of one of today’s most stylish young stars wearing one of red carpet’s most talented designers is always a guaranteed winner. The Grecian-style drape, the subtle brown tones, the asymmetry of the one-shoulder cut on Zendaya’s long, lithe frame was a salute to Giambattista Valli’s sensual design skills.


16. Gemma Chan in Valentino (2019) — attendee
From the runway to the red carpet, voluminous dresses are the new statement, and Gemma Chan made a brave entrance in her ruffled hot pink Valentino (with pockets) in 2019, fresh from her success in Crazy Rich Asians. An immediate hit with the critics, this trend was embraced by more stars who followed suit. (Kathryn Newton just donned a similarly gorgeous Valentino style in tangerine for the SAG awards ceremony, making all the best dressed lists.)

17. Amandla Stenberg in Miu Miu (2019) — presenter
A star in the making, this young talent proved that youth is no barrier to carry off such classic vintage elegance. Stenberg teamed with Miuccia Prada for this 1920s-inspired silver beaded column gown with a subtle sheer lining, looking every inch a goddess.


18. Naomi Watts in Armani Prive (2013) — nominee, Best Actress, The Impossible
Both Naomi Watts and Giorgio Armani are noted for their red carpet triumphs, so together they made a formidable pair. This highly polished design in metallic gunmetal gray, with its geometric cut, was just sublime and deservedly made many Oscars “Best Dressed” lists.

19. Lupita Nyong’o in Prada (2014) — winner, Best Supporting Actress, 12 Years a Slave
This ice-blue pleated chiffon dream dress was as notable for the joyful spirit of Lupita Nyong’o and her delight at wearing it, as it was for the exquisite design, color and fit. Unforgettable in her win, the actor was 2014’s belle of the ball.

20. Ava DuVernay in Ash1 Studio (2017) — nominee, Best Documentary, 13th
In addition to looking stunning, Ava DuVernay wore a statement of support to complement the subject of race and injustice in the U.S. prison system, which she covered in her revered documentary. Her 2017 Oscars look was a silver lace and organdy custom gown designed by Ashi Studio (Mohammed Ashi), a designer from Lebanon, a majority Muslim country.


Feature image: LUPITO NYONG’O in PRADA at the 2014 Academy Awards, at which she won Best Supporting Actress for her role as Patsey. Photo by Jason Merritt/Getty Images.


Feb. 4, 2020

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