top of page
FRAMES_Oscars Fashion_03.JPG
FRAMES_Oscars Fashion_04.JPG

Decades of Best Supporting Actress Oscars' Fashion

by Majo Aguilar

The Academy Awards have just turned ninety-five years old, with just a few lustrous more to celebrate their first century of life.

In the motion picture industry, women have always earned less recognition and economic reward, but women are also often the focal point of the awards. When it comes to Oscars fashion, audiences are never interested in the tuxedos, but in the dresses worn by the female actors. The image of the Best Supporting Actress is often transfixed in memory along with their work, and represents the time period in which that image lives. While a motion picture tells us a lot about the film industry at the time, social context, and political context, a single picture can tell a similar story through fashion. 

The Best Supporting Actresses also deserves to have their name (and their dress ) written in history and collective memory. That's why Portray-TS Digital Magazine journeys through the almost ninety-five years of The Academy, and winks at our Editor-in-Chief's love of fashion. Read below for some of our Best Supporting Actress fashion and how their choices reflect the decade and tradition of moving pictures. 


1937 marked the first time The Academy awarded the statuette for Best Supporting Actress, with the first-ever winner being Gale Sondergaard for the film Anthony Adverse directed by Mervin LeRoy, starring Olivia De Havilland and Fredric March. The winner opted for a sleeveless  black and white floral patterned design with a buttonhole collar. This dress represents the sober silhouette of pre-war fashion, a classic cut and neutral colors. The 1930s saw a rise in conservatism following the 1920s' glamour. As opposed to the "boyish" or "gamine" Chanel-influenced fashion, women wore more feminine silhouettes with a focus on the shoulders. The dress is a timeless choice that could be worn decades later. 

Sobering Silhouettes 


Alice Brady won for In Old Chicago, starring heartthrob Tyrone Power and Alice Faye, but unfortunately couldn’t attend the ceremony due to a broken ankle. Her absence, however, led to one of the most memorable incidents in Oscar history - the story goes that an anonymous person attended on her behalf to accept the award, but the mysterious man was never found and her award never appeared. In 2008, The Academy confirmed that a replacement was handed to her. Security levels at the ceremony have increased since then. 


Fay Bainter had a role in one of the most iconic Hollywood films ever made, the classic southern drama Jezabel directed by icon Billy Wilder and starring one of silver screen’s biggest dames, Bette Davis, alongside Henry Fonda. Fay Bainter wore a gorgeous and, once again, very 1930s gown to receive her statue. Interestingly, her choice to wear transparent tulle was a more rebellious detail of the time. Fay is photographed alongside studio executive Jack Warner from Warner Bros. and her fellow cast partner Bette Davis.

Screen Shot 2023-04-17 at 4.19.59 PM.png


Mary Astor is the perfect example of what fashion looked like through the 1940s. In wartime style, her dress is different from the opulent dresses of the past due to textile rationing. Colors were dark at the time, and shapes were simple to save fabric and time. Astor's pencil cut dress is layered with a minimalist cloak and clasp. The winner for The Great Lie directed by Edmund Goulding and starring Bette Davis and George Brent is happily pictured after her triumph.


As fabrics become more available at the end of the war, fashion items became more complex. Katina Paxinou, the winner, photographed with Paul Likas and Jeniffer Jones on her left and Charles Coburn on the right, wore the infamous “shoulder pads” or epaulets that became so popular in the mid 1940s. They were desired for the broad and pointy effect they gave which created an illusion of a slimmer waist. The style was replicated across every-day fashion like blazers and coats. This trend would reappear in the 1980s with a more juvenile re-imagination. The greek was crowned for For Whom the Bell Tolls directed by Sam Wood and starring Gary Cooper and Ingrid Bergman


In pure Cinderella fashion (and looking like a princess herself) Celeste Holm attended the ceremony wearing what would become the signature gown cut in the decade to come. With a leafier and wider skirt and a more detailed and romantic trunk, the dress is a hint of what Christian Dior would present a year later, the famous and revolutionary Dior look, which changed fashion forever. She won for Gentlemen's Agreement directed by legend Elia Kazan and starring Gregory Peck and Dorothy McGuire.


Gloria Grahame has her hand kissed by kneeling Edmund Gwenn after winning for The Bad and the Beautiful with Lana Turner and Kirk Douglas, directed by one of Italy’s greatest exports, Vincente Minelli. In typical 50s fashion, Grahame wore a dreamy dress with a heart-shaped corset. The novelty and fun aspect about the design was its length at the calf demonstrating that even shorter options can still be elegant. 


One of Hollywood’s most talented and gorgeous blondes at the time, Eva Marie Saint, Marlon Brando’s eternal on-screen love, took the award home in her film debut, the classic drama, On the Waterfront directed by Elia Kazan and starring Brando alongside Karl Malden. Saint is one of the few classic hollywood stars that are still fortunately among us - she remains healthy and beautiful at the age of 98! In fact, the icon was invited to the 2018 edition of the Academy Awards to present Best Costume Design. For her special night she jazzed up the typical award look and wore a two-piece pearl white suit, consisting of a jacket and a pencil skirt of satin fabric with a discreet brocade. At the time it was an innovative choice that contrasted the widely worn strapless dress and wide skirt.


Embracing her culture, Miyoshi Umeki wore a traditional Japanese kimono to receive her award for Sayonara, the technicolor drama-romance directed by Joshua Logan and starring the it star at the moment, Marlon Brando and Umeki herself. She was the first ever Asian woman to win the award, and paved the way not only for Asian female performers and directors, but to the Asian community involved in the motion picture business. Her dress is a statement of embracing your culture and feeling proud and confident. 



Rosa Dolores Alverío, better known as Rita Moreno, starred in a historical moment at the 1962 ceremony. She not only won for her role as Anita in the adaptation of Broadway's hit West Side Story directed by Robert Wisse and Jerome Robbins, but became the first latina to ever receive the accolade. Rita told E! Entertainment that her now iconic gown was confectioned in Manila, Philippines. The design is one of the most exquisite pieces ever worn to the awards - a skirt printed with golden brocade and a black top that matches the traditionally elegant long gloves. This piece is timeless.


Rita spectacularly reappeared wearing this dress with just little modifications at the age of 86 in the 2018 edition of the Oscars, looking like an absolute goddess. What makes Moreno’s win so special and different from others is the heartwarming moment when the diva was able to witness actress Ariana DeBose win for the same role as she did sixty years before, during the 2021 Oscars. DeBose thanked Rita, who was visibly moved. This has been one of the only two times that an actor or actress has been awarded by reprising a role another actor played before, the other case had been that of Robert De Niro and Marlon Brando, who played Vito Corleone on different occasions.


Lila Kedrova, the French-Russian theater star, won her first award due to a screen role for her performance in Zorba the Greek, directed by Michael Cacoyannis and starring Anthony Quinn. This wasn't the first time Lila got recognition for her role as Madame Hortense, since Zorba was also a very popular Broadway production, the critics crowned her with her first Tony as well. Kedrova wore a dark, sleeveless, straight-cut dress with matching gloves in a Jackie Kennedy style. She proved that the upcoming trends of one of the most spectacular decades in fashion wasn't only for the younger generation. Her outfit was a lesson that women of any age could be part of the rising mod fashion.


Ruth Gordon had been there since the beginning of it all. Born in 1896 and being credited in a movie for the first time in 1915, more than anyone, she knew what filmmaking was all about. Gordon is one of the most underrated actresses ever. She managed to have a successful career that spanned seven decades and overcame the terror of many actors and the motive that ended tons of careers: talkies. She won for her role in Roman Polanski’s Rosemary’s Baby at the age of 73. Ruth wore a very classic Barbie pink dress with long sleeves and a circular neck, the design´s cut is a timeless and forever elegant cut that is reinvented with an interesting feathered detail around the waist. Finishing the outfit with pearl jewelry, her attire is everything we can expect from a diva of the big screen.


New decade, new trends - that’s the rule. Cloris Leachman proves it just right. The winner wore an extremely minimalistic dress, a black spaghetti strap design with no jewelry. The complicated and structured dresses from the 40s or the puffy skirts of the 50s and 60s were gone, the 1970s introduced a much simpler elegance which was intended to elongate the figure. Leachman’s dress will forever be a fantastic choice, little black dresses never go out of style. She received the Oscar for her performance in the coming of age film The Last Picture Show directed by American cinema icon Peter Bogdanovich, she shared the screen with then rising stars Cybill Shepherd and Jeff Bridges. She’s photographed alongside Raquel Welch and Gene Hackman.


Ingrid Bergman is one of the most brilliant and gorgeous actresses that ever graced the screen. Her work in American and international cinema positioned her as the fourth greatest classic cinema star according to the American Film Institute. Bergman’s win is different, while other actresses pursue the best actress award for years and get nominated for best supporting actress instead, Bergman had previously won two Oscars for best actress, first in 1944 for George Cukor’s Gaslight, and for the second time in 1956 for Anatole Litvak’s Anastasia.


The swede had never been nominated for best supporting actress until 1975, when she won for Murder in the Orient Express, which is one of the first movies ever to have an all-star cast - Lauren Bacall, Albert Finney, Sean Connery, John Gielgud, Jean-Pierre Cassel, Vanessa Redgrave, Michael York, Rachel Roberts, Jacqueline Bisset, Anthony Perkins, Richard Widmark and Wendy Hiller, and directed by Oscar winning Sydney Lumet. Ingrid Bergman wore a loose and boho-chic flower patterned dress in pastel tones made of light and flowy fabric that still reminds us of the flower child fashion that was still strong at the beginning of the decade. The design enhances her natural beauty and warm undertones.

Flower Child


Dame Maggie Smith won her second Oscar for California Suite, directed by Herbert Ross. This film had an all-star cast once again - Smith shared credits with Jane Fonda, Bill Crosby, Richard Pryor, Eileen May and Michael Caine. In the dying days of disco, Dame Maggie Smith wore a dress reminiscent of the usual attire worn at Studio 54, a shiny metallic brocade top and a flowy straight black skirt, the balance of sobriety and brightness perfectly marked the end of the decade, as well as the slight hint that in the coming decade people would crave wild volume. Maggie is photographed alongside rising star Brooke Shields.


This is the first of three times that fan favorite Meryl Streep won an Academy Award for her role in Kramer vs Kramer, directed by Robert Benton and starring Dustin Hoffman. Two years later, she would win as best actress for Sophie's Choice and again in the same category in 2011 for The Iron Lady. She remains as the most nominated actress of all time, with 21 nominations. Streep wore a cream colored coat-like gown by Pauline Trigère, showing clear influence of the 1940s in reincorporating shoulder pads, structured tops and heavy fabrics  in fashion, her choice is of a very similar style to the dress that Ingrid Bergman wore to the 1944 edition of the Awards.


Anjelica Huston was crowned best supporting actress for her role in Prizzi’s Honor. It was a very emotional and special win for her since she was directed by her father, legend John Huston, and shared the screen with the love of her life, actor Jack Nicholson, with whom she had a fifteen year long on and off relationship. Huston stole the show with an emerald green one-sleeve creation by costume designer Tzetzi Ganev. Her gown might be one of the most spectacular dresses ever worn to the Academy Awards - it’s an outstanding dress among the usual 1980s over-the-top choices. It’s simplicity and lightness enhances Anjelica’s height and gives off classic Hollywood vibes in a very Evelyn Hugo kind of way. 


Geena Davis summarized the eighties with this baby blue dress. It has it all: shiny fabric (most likely to be satin), volume, colorful shoes and sheer stockings. The more, the better. In a modern context of what award fashion should be, this dress might feels dated (because it is), but back then this was all the rage, and a dream dress for many. This is the time when many stars showed some of their personality through their clothes, and not everyone needed or had a stylist. Davis won for The Accidental Tourist, directed by Lawrence Kasdan and starring William Hurt.


Something more classic than a black and white Chanel gown? I don’t think so! Marisa Tomei  looked dazzling in one of the most timeless brands of all time. The A-cut skirt and jewel neckline will forever distinguish the french haute-couture house and favor any body type at any age and for every occasion. Tomei brought back the original elegance of the Oscars with a pair of black gloves and a classic updo. This is a major throwback to the golden age of movies. Marisa won for My Cousin Vinny directed by Jonathan Lynn and starring Joe Pesci.


Apparently, the 90s were a decade that fell in love with the fashion of the 1950s, the proof is Mira Sorvino’s pale blue Armani dress, with a strapless heart shaped top and a full skirt. This dress could have been perfectly worn forty years back by Grace Kelly or Sophia Loren. Her look is complemented and enhanced by the gorgeous clear jewelry and wavy updo. Sorvino won for Woody Allen 's Mighty Aphrodite.

The 1990s Welcomes the 1950s


Kim Basinger paid the ultimate homage to classic Hollywood. The actress, who won for Curtis Hanson’s L.A. Confidential starring Russell Crowe, made an evident tribute to Grace Kelly not only by wearing a very similar dress in color and shape, but by wearing similar hairstyle and makeup to the one that the future Princess of Monaco had in the 1955 edition of the Academy Awards. The creation by Escada once again demonstrated that less is more, and simplicity is often the ultimate elegance.


The cute girl next door from the eighties, Jennifer Connelly, was now a gorgeous young woman who had just been crownd best supporting actress for her performance in Ron Howard’s A Beautiful Mind, starring alongside Russell Crowe. It was the beginning of the millennium with Y2K fashion taking over. It is no secret that fashion in the beginning of the 2000s was somewhat...experimental. Jennifer wore a nude Balenciaga dress that gave the illusion of being ripped, paired with a yellow scarf. Jennifer certainly encapsulated the first decade of the millennium. 


The iconic Cate Blanchett won her first Oscar for Martin Scorsese’s The Aviator, where she played another iconic woman, Katherine Hepburn, who turns out to be the actress with the most Academy Awards in history, a total of four, which ironically she never attended to pick up. Valentino was Cate’s chosen designer. Cate Blanchett showed once again her great taste for silhouettes. In classic Y2k aesthetic, she wears a pastel colored dress amongst the technicolored crowd. 


The Spanish diva Penelope Cruz wore a white Balmain design to pick up her award for her role in Vicky Cristina Barcelona, directed by Woody Allen and starring Scarlett Johansson and Cruz’s husband Javier Bardem. The princess-cut lace gown is a fairytale dream, the discrete silver scaling across the torso and skirt brightened up the actress, who accessorized the strapless dress with silver jewelry. Once again, classics will forever be in vogue.


The 2010s were the year of solid color dresses, Anne Hathaway paved the way with an extremely elegant pale pink Prada gown and silver jewelry. Anne, who won for Les Miserables by Tom Hooper, made a last minute change and dressed in this gorgeous, clean-cut halter neck and crossed back design instead of the original Valentino dress she was planning to wear to the ceremony. 


Prada had another hit during the 2014 ceremony, where then newcomer Lupita Nyong´o wore a pale blue 70s inspired gown, similar to the pastel Halston design Lauren Hutton wore to the 1975 Oscars and model Elsa Hork re-wore to Cannes 2019. The design is of extreme simplicity but the V neckline and wide skirt are enough to make this dress extremely stylish. She finished the look with a silver headband. Lupita won for her role in Twelve Years a Slave, directed by Steve McQeen, one of the most talented directors of modern cinema.


Alicia Vikander resembled princess Belle in this yellow Louis Vuitton dress, the asymmetrical skirt and strapless top were decorated with silver applications and matched with silver platforms, also designed by Louis Vouitton. The Swede shined like no other, not only because of her triumph for The Danish Girl directed by Tom Hooper, but because the dress enhanced her natural beauty and warm undertones.


We are just starting the 2020s, three years into the decade aren’t enough to choose our favorite dresses yet, but we can certainly say that Laura Dern inaugurated this new decade with a gorgeous Oscar de la Renta gown in pale pink and black applications. Dern looked spectacular, but the cherry on top of her win for Noah Baumbach’s Marriage Story is that she won it on her birthday. Wearing beautiful gown and winning an Academy Award seems like the perfect way to celebrate such a special day.

bottom of page