Oscars:Best dresses of all time (right to left) Hillary Swank, Janelle Monae, Jane Fonda
This year, perhaps more than ever, Hollywood’s biggest stars are expected to hit the red carpet in the daring looks we have been waiting for. All, of course, with the help of their professional stylists who I’m sure have been hitting all the fashion and couture shows to make sure they don’t skip a beat.
Ahead of this year’s awards, we look back at some of the very best Oscars looks of all time.
These dresses made an impact not just in the fashion industry but in the cultural zeitgeist.
These Oscar gowns also made fashion icons out of the actresses who wore them.
Best Oscars red carpet dresses of all time
Sharon Stone in GAP and Vera Wang, 1998
Some looks are going to be unexpected and that is just why they made the list! Remember Sharon Stone in 1998, in a white button-down shirt from the GAP, rumored to belong to her husband at the time, and a skirt from Vera Wang which together played up masculinity and femininity?
This same look showcases mixing high and low brands which at the time was unheard of for the red carpet. Lastly, this look is as modern today as it was then; inspiring a fresh, sophisticated, sexy style that became an instant classic and has been adopted by many actors since.
The Oscars: Sharon Stone in GAP and Vera Wang in 1998
The Oscars: Nicole Kidman, with Tom Cruise, wearing 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 motif and luxe silk fabric in the perfect shade of chartreuse.
Paired with frosted blue slingbacks, a ladylike chinoiserie clutch, and dramatic chandelier earrings, this look showed how accessories can elevate a beautiful gown into a memorable moment.
I think this dress became Nicole’s benchmark for red carpet style, she clearly takes pride in prompting non-stop iconic moments and fashion-forward looks every year. This dress was a defining moment in her fashion career.
Halle Berry in Elie Saab, 2002
In 2002 Halle Berry made history multiple times. She was the first African American woman to win best actress. She also made history by being the first American actress to ever wear Arab couture designer Elie Saab and introduce him to the western world.
The dress, with very artfully placed embroidery, was customised perfectly for her silhouette, giving old Hollywood glamour with new Hollywood sex appeal.
Mila Kunis in Elie Saab, 2011
In 2011 Mila Kunis’s Elie Saab chiffon and lace lavender dress played the perfect melody of glamour, femininity and elegance.
Mila’s dress became a huge fashion moment for all ages.
Inspired by the look, some well-known fashion brands replicated the gown for their prom and others for their bridal lines. This look is one of Mila’s finest fashion moments.
Jane Fonda in Balmain, 2018
That hair! That body! That posture! That confidence and that dress! She literally redefined what it is to be 80; not only in the industry but the world.
This look is so important to our culture today and for the 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 end at a certain age. Nor does this best-dressed list. She is legendary.
The Oscars: Halle Berry making history wearing Elie Saab in 2002
The Oscars: Mila Kunis at The Oscars wearing Elie Saab in 2011
Jennifer Lopez in Valentino, 2003
This was a different kind of daring for actress Jennifer Lopez.
This was an homage to America’s fashion icon Jackie O, which showed that Jennifer had the range to create timeless classic style moments as well as offer daring sex appeal.
This dress brought back one shoulder to evening wear for the next few seasons. The color pistachio became more mainstream for red carpets, evening wear, and especially the bridal market.
The Oscars: Jane Fonda wore Balmain on the red carpet in 2018
The Oscars: Jennifer Lopez in Valentino at the 2003 Academy Awards
Jessica Alba in Versace, 2006
This dress at the Oscars was a defining moment in my own fashion career. I was interning at Vogue and this Couture gown by Versace was what made me not just dream about fashion, but realise it was my destiny.
At a time when starlets were running around Hollywood in juicy couture tracksuits and the fashion trends on most magazine covers were for club attire; here comes Jessica Alba showing chic femininity and elegance.
She was exuding class and grace like a royal. The color of the lace was perfect for Jessica’s skin tone and silhouette; it kept her perfect for an Oscars among the icons while showcasing her youthful glow.
The Oscars: Jessica Alba at the Oscars in wearing Versace in 2006
The Oscars: Hillary Swank winning 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 sapphire blue backless long sleeve Guy Laroche gown, which showcased her sculpted body as his “muse”.
This gown highlighted American fashion with a twist. It brought back the long sleeve gowns and high necks of previous eras but introduced a whole new low for the back of a gown.
Many celebrities have tried to mimic this down’s low back drama, but none have managed it with quite as much class and flair.
The Oscars: Gwyneth Paltrow wore Ralph Lauren at 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 bubblegum pink taffeta spaghetti-strapped ball gown that channeled Grace Kelly.
The clean classic American style worked perfectly for Gwyneth Paltrow’s all-American-girl persona.
After her style moment, the color bubble gum pink reemerged for evening wear as a classic shade. This gown would become a hit with prom dresses for years and 23 years later the company ASOS recreated the iconic dress.
Janelle Monae in Elie Saab, 2017
Janelle Monae’s 2017 Elie Saab gown was a live piece of art. The dramatic couture gown with the perfectly placed applique and diamond crystals gave us a fairy tale that starred a Queen.
That year was her first Oscars, and with two films nominated (Moonlight and Hidden Figures) she knew to bring the award-winning drama to the red carpet and make an Oscars-worthy statement.
Engie Hassan is a royal and celebrity stylist, costume designer and Vogue Alum. For red carpets Engie has styled Priyanka Chopra, Jeremy Piven, Joshua Henry, Taryn Manning, Rizwan Manji (Schitt’s Creek), comedienne Maysoon Zayid, Antoinique Smith and many others. Her Cannes styling for Indian actress and activist Fagun Thakar secured best dressed lists including Vogue, Elle, Harper’s Bazaar, The CUT and more.
For personal styling 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.