Oscars: Best Dresses Ever (right to left) Hillary Swank, Janelle Monae, Jane Fonda
This year, perhaps more than ever, Hollywood’s biggest stars are set to hit the red carpet in the daring looks we’ve been waiting for. All of this, of course, with the help of their professional stylists who I’m sure have been on every fashion and couture show to make sure they don’t skip a beat.
Ahead of this year’s awards, we take a look back at some of the best Oscar looks of all time.
These dresses have made an impact not only in the fashion industry, but also in the cultural zeitgeist.
These Oscar dresses also made fashion icons the actresses who wore them.
The Best Oscars Red Carpet Dresses Ever
Sharon Stone in GAP and Vera Wang, 1998
Some looks are going to be unexpected and that’s why they made the list! Remember Sharon Stone in 1998, in a white GAP button-down shirt, believed to belong to her husband at the time, and a Vera Wang skirt that together played off masculinity and femininity?
This same look features a mix of high and low marks which at the time was unheard of on the red carpet. Finally, this look is as modern today as it was then; inspiring a fresh, sophisticated and sexy style that became an instant classic and has been embraced by many actors since.
The Oscars: Sharon Stone in GAP and Vera Wang in 1998
The Oscars: Nicole Kidman, with Tom Cruise, in Christian Dior Couture in 1997
Nicole Kidman in Christian Dior Couture, 1997
The elegant Asian-inspired silhouette of Nicole Kidman’s 1997 Christian Dior Couture gown featured an embroidery design and luxe silk fabric in the perfect hue of chartreuse.
Paired with frosted blue pumps, a feminine chinoiserie clutch and dramatic chandelier earrings, this look showed how accessories can turn a beautiful dress into a memorable moment.
I think this dress has become Nicole’s go-to for red carpet style, she clearly takes pride in sparking non-stop iconic moments and fashion-forward looks every year. This dress was a watershed moment in her fashion career.
Halle Berry in Elie Saab, 2002
In 2002, Halle Berry made history several times. She was the first African-American woman to win the Best Actress award. She also made history by being the first American actress to wear Arab couture designer Elie Saab and introduce him to the Western world.
The dress, with very artfully placed embroidery, was perfectly tailored to her figure, giving old Hollywood glamor with new Hollywood sex appeal.
Mila Kunis in Elie Saab, 2011
In 2011, Mila Kunis’ lavender chiffon and lace dress Elie Saab played the perfect melody of glamour, femininity and elegance.
Mila’s dress has become a big fashion moment for all ages.
Inspired by the look, some well-known fashion brands replicated the dress for their prom and others for their bridal lines. This look is one of Mila’s finest fashion moments.
Jane Fonda in Balmain, 2018
This hair! This body! This posture! That confidence and that dress! She literally redefined what it’s like to be 80; not only in the industry, but in the world.
This look is so important to our culture today and for generations to come.
Where ageism tries to define women in Hollywood, Jane breaks the code and inspires generations of women that self-love, fashion, glamour, beauty and work do NOT stop at a certain age. . Nor this best dressed list. She is legendary.
Oscars: Halle Berry made history as Elie Saab in 2002
The Oscars: Mila Kunis at the Oscars in Elie Saab in 2011
Jennifer Lopez in Valentino, 2003
It was a different kind of daring for actress Jennifer Lopez.
It was a tribute to American fashion icon Jackie O, who showed Jennifer had the ability to create timeless classic style moments as well as deliver bold sex appeal.
This dress brings one shoulder back to evening wear for the next few seasons. The pistachio color has become more common for red carpets, evening wear and especially the bridal market.
The Oscars: Jane Fonda wore Balmain on the red carpet in 2018
Oscars: Jennifer Lopez in Valentino at the 2003 Oscars
Jessica Alba in Versace, 2006
That Oscar dress was a watershed moment in my own fashion career. I was interning at Vogue and this Versace Couture dress made me not only dream of fashion, but also realize that it was my destiny.
At a time when starlets roamed Hollywood in juicy couture tracksuits and the fashion trends on most magazine covers were for club wear; here is Jessica Alba showing chic femininity and elegance.
She exuded class and grace like a royal. The color of the lace was perfect for Jessica’s complexion and figure; it kept her perfect for an Oscar among icons while showcasing her youthful glow.
The Oscars: Jessica Alba at the Oscars in Versace in 2006
The Oscars: Hillary Swank wins the Oscar for Million Dollar Baby in 2005 wearing Guy Laroche
Hilary Swank in Guy Laroche, 2005
The night Hilary Swank accepted the Oscar for Million Dollar Baby in 2005, she donned this stunning long-sleeved, open-back sapphire blue dress by Guy Laroche, which featured her sculpted body as her “muse.”
This dress underlined American fashion with a twist. It brought back the long-sleeved and high-necked dresses of earlier eras, but introduced an all-new low for the back of a dress.
Many celebrities have tried to emulate lower back drama, but none have managed it with such class and flair.
The Oscars: Gwyneth Paltrow wore Ralph Lauren to the Oscars in 1999
The Oscars: Janelle Monae wore Elie Saab at the Oscars in 2017
Gwyneth Paltrow in Ralph Lauren, 1999
Gwyneth Paltrow wore Ralph Lauren’s candy pink taffeta spaghetti strap ballgown which featured Grace Kelly.
The clean, classic American style worked perfectly for Gwyneth Paltrow’s all-American character.
After its style moment, the color bubble gum pink has reappeared for evening wear as a classic hue. This dress would become a hit with prom dresses for years and 23 years later the company ASOS has recreated the iconic dress.
Janelle Monae in Elie Saab, 2017
Janelle Monae’s 2017 Elie Saab dress was a live work of art. The dramatic couture gown with the perfectly placed applique and diamond crystals gave us a fairy tale featuring a queen.
That year was her first Oscars, and with two nominated films (Moonlight and Hidden Figures), she was able to bring the award-winning drama to the red carpet and make an Oscar-worthy statement.
Engie Hassan is a Royal and Famous Stylist, Costume Designer and Vogue Alum. For the red carpets, Engie has styled Priyanka Chopra, Jeremy Piven, Joshua Henry, Taryn Manning, Rizwan Manji (Schitt’s Creek), comedienne Maysoon Zayid, Antoine Smith and many more. Her Cannes style for Indian actress and activist Fagun Thakar has landed best-dressed lists including Vogue, Elle, Harper’s Bazaar, The CUT and more.
For personal style and other events, she has worked with Orlando Bloom, Kanye West, Miranda Kerr, Lady Gaga, Andre Holland, Amir Arison and more. Hassan is a costume designer and wardrobe stylist for over a dozen film and television projects, including 3 films premiering this year.