The best and most subversive Oscars fashion moments

When the Oscars first started in 1929, many of the attendees who weren’t frequenting high society galas or parties didn’t know how to dress for the awards. However, one of the first people who harnessed the event and the power of image was Bette Davis. By 1936, Bette was locked into a ferocious and very public legal battle with Warner Brothers. She, as well as other actors and actresses, were fighting to have the artistic freedom to pick and choose what films they’d like to star in.

Bette did not win the lawsuit, so instead, that year at the 1936 Academy Awards, she accepted the award for Best Actress for Dangerous in a maid’s uniform. The costume, which was intended for the 1934 film Housewife, signalled that Bette thought that actors were being treated like ‘hired help’.

“That was her way of protesting without being too verbal,” Dijanna tells The Weekly. “Because she was still contracted to the system and she still had to work.”

“That was the first time that someone really took the red carpet and made a statement of their own on it.”

Just three years later, Bette made another fashion statement at the Oscars when she once again dipped into the costume trope for the red carpet. This time, to accept her second Academy Award, the actress donned a Collette gown with an Elizabethan feathered collar. This was apt considering that Bette had just shot The Private Lives of Elizabeth and Essex that year.

Though it was just three years ago Bette brought the secretive politics of Hollywood to the Oscars red carpet, now on that same platform, she was crowning herself as Hollywood royalty.

“Bette took all those royalty tropes that she was using in the movie, and translated them to her red carpet gown to make a statement that she is the queen of Hollywood – and that visual totally worked,” Dijanna says.

For actress Olivia de Havilland, the Oscars red carpet wasn’t so much a place to protest as it was a place for a PR refresh. Like Bette and hundreds of other actors, Olivia felt the wrath of the stringent and harsh contracts placed upon her by film studios.

In search of better movie roles in the mid-1940s, Olivia began turning down roles offered to her by Warner Brothers. This resulted in Jack Warner punishing her by suspending her from acting altogether. Then, once Olivia’s seven year contract ended, Jack attempted to extend it by arguing that Olivia owed him for the time she missed while suspended.

Olivia took Warner Brothers to court and won her case, resulting in what is now called the De Havilland Law. Though this saw her ostracised for a few years, it also let Olivia seek out more fulfilling acting opportunities such as Catherine Sloper in The Heiress (1949) – a role which landed the actress her second Oscar win for Best Actress.

However, Olivia felt that her legal battle with Warner Brothers as well as her highly publicised feud with her sister, Joan Fontaine, could spoil her public image. So she turned to Orry-Kelly for help.

Orry-Kelly, who was an Australian costume designer, dressed Olivia in a dreamy white chiffon gown for the 1950 Oscars. The crown jewel of the outfit was the fabric daisies which were stitched to the skirt of the dress to promote the sense of being sweet, innocent and ‘fresh as a daisy’.

At a time where Oscars attendees donned dresses with miles and miles of pastel tulle, Marlene Dietrich not only subverted the norm, but she stole the show. The actress, who had been overlooked for her stellar performance in Alfred Hitchcock’s Stage Fright, was relegated to presenting awards alongside a little-known actress at the time – Marilyn Monroe.

Marlene called upon Christian Dior, who at that point had become a world famous designer, to craft the perfect gown for the evening. In total opposition to the princess-y ballgowns donned by some of the younger women in attendance, 51-year-old Marlene Dietrich stepped out in a racy, fitted black cocktail dress with an ultra-daring thigh-high split.

“It’s really interesting, because when you look at how Marilyn Monroe dresses almost immediately after that, she started to wear the more straight silhouettes. I feel like she definitely took a masterclass from Marlena Dietrich that night,” Dijanna explains.

In 1969, Barbra Streisand was up for her very first Oscar award. The vocal powerhouse had two options for the red carpet, play it safe with a traditional Dior gown, or push the boundaries with a gender-defying Scaasi two-piece suit. Barbra, of course, chose the latter.

Inspired by Yves Saint Laurent’s 1966 Le Smoking suit, the Scaasi ‘party pyjamas’ featured sheer fabric, bell-bottoms and a constellation of sparkling paillettes. Though these paillettes shimmered under the lights as Barbra walked on stage to claim her award for Best Actress, the sheer nature of the suit also rendered her buttocks semi-exposed.

Though some described the moment as one of the most ‘shocking’ in Oscars red carpet history, it not only cemented Barbra as a style icon, but the media coverage of the outfit catapulted her career to new heights.

Jane Fonda‘s career has been full of subversive moments, either through actual protest or implied, like this instance here. Off the back of her residency in France and her appearance in Barbarella (1968), Jane became a sex symbol, something she was desperately trying to eschew.

And so, when she was nominated in 1972, Jane appeared at the Oscars to accept the award for Best Actress with a new look. Jane donned a trim Yves Saint Laurent Rive Gauche black suit that was inspired by an anti-Vietnam protest in Paris.

Not only did Jane’s new look reject the objectification of her sex symbol status, but it was already deeply rooted in the activism that would go on to define her career.

Before Princess Diana stepped out in that daring Christina Stambolian cocktail dress that we now famously refer to as ‘the revenge dress’, Cher had her own ‘revenge dress’ moment eight years prior. It’s hard to remember any other Oscar Awards attendee in 1986, and that’s exactly what Cher wanted.

The singer-turned-actress was deeply disappointed when her performance in Mask was completely overlooked by the Academy, so she turned to Bob Mackie for help. Together, with a sketchpad in a New York hotel room, she and Bob sketched an utterly glamorous and outrageous outfit that would bring the attention back to her.

Featuring a feathered headpiece, a satin robe, a sequined skirt with a sharp scalloped hem that poked the hip bones and a tiny bralette, Cher had jaws dropping at the 1986 Oscars.

“It was just genius, she made the Academy pay for it. And it worked. Because a couple of years later, she did in fact win Best Actress,” Dijanna explains.

So, you’re going to a pretty big party, and you know your ex is going to be there. What do you do? Well, if you’re Madonna, you call up the King of Pop and bring the date of all dates.

Madonna had been invited to perform the Oscar-nominated hit Sooner or Later from the film Dick Tracy, which she starred in alongside Warren Beatty. Having split with Warren just months prior to the awards show, Madonna decided to make a splash at the event.

Not only did she show up hand-in-hand with Michael Jackson, but she donned a Bob Mackie design and paid homage to her icon, Marilyn Monroe, in a glittering white dress, golden curls, red lipstick and a fur coat.

At the Oscars, usually our eyes are glued to the A-Listers floating down the carpet in haute couture. However, when Lizzy Gardiner, an Australian costume designer, hit the 1995 red carpet, she stole the show. Lizzy and her co-costume designer, Tim Chappel had been nominated for an Oscar for Best Costume for their work on the seminal film, Priscilla Queen of the Desert.

Rather than a traditional gown, Lizzy showed up in this splendid creation which featured 254 expired American Express Gold cards. The dress was originally meant for the Priscilla film, but American Express wouldn’t give her permission to use it on screen.

“I’m broke, and I didn’t have anything to wear. So I went through my list of past good ideas,” Gardiner was quoted saying at the time.

“If she had opted for something more traditional, she wouldn’t have made the splash she did,” Dijanna says. “People had all these different interpretations of what the dress meant, was it a representation of the materialism that was at the forefront of people’s minds in the 80s? Was it a jibe to people who spent thousands of dollars on the red carpet? Or was it an homage to the 60s panel dresses?”

Critics at the time weren’t nearly as kind in their interpretations of the dress; both Cosmopolitan and Time Magazine cited the dress as one of the ‘worst of all time,’ with Time even labelling the design as “tacky”. However, it is this exact surrealism that defines many high fashion collections 30 years on.

Much like Lizzy Gardiner, Nicole Kidman also unfairly found herself on a number of ‘worst dressed’ lists when she wore this satin chartreuse John Galliano gown at the 1997 Oscars. Outspoken fashion critic Joan Rivers lambasted the Australian actress from over the velvet ropes shouting the gown was “the ugliest thing I’ve ever seen”.

Whilst the dress lived on in infamy (even scoring itself its own dedicated Wikipedia page), Dijanna says that this marked a real turning point for red carpet fashion.

“These harsh remarks from Joan Rivers are linked to a turning point in Oscars red carpet history when risks became calculated and anything remotely original in the way of self-styling was replaced by professional advice and safe sartorial choice,” Dijanna tells The Weekly.

In 2002, Halle Berry made Oscars red carpet history when she became the first Black woman to win an Oscar for Best Actress for the film Monster’s Ball. In anticipation of potentially not only being recognised by her industry, but making history, Halle Berry turned up in this dreamy gown by a then little-known designer, Elie Saab.

“I think there was a very purposeful choice to wear something sheer and show as much Black skin as possible for such a historical and defining moment,” Dijanna says.

Not only does the Oscars red carpet catapult the careers of stars, but designers, too. 15 years on from dressing Halle Berry for her momentous win, Elie Saab quickly became a fashion mainstay in red carpet fashion. In 2017, he dressed Janelle Monae in this opulent spin on an 18th century robe à la française gown.

“She was not nominated for anything, but she starred in two of the films that were up for best picture, so I think she felt like that was her princess moment… that gown says, ‘I’m here,'” Dijanna says.

In 2018, Hollywood was well and truly in the throes of the Time’s Up and #MeToo movement. The conversation dominated headlines, social media and the Oscars red carpet. Countless celebrities used the red carpet and the awards to either make a verbal statement or one through their fashion.

Jane Fonda, who is no stranger to communicating through fashion, opted for a very plain white gown to contrast with the Time’s Up pin.

“She made sure she was a billboard for that message,” Dijanna explains.

For the 2019 Oscars, we started to see the men of Hollywood bring their A-game. Actor Billy Porter teamed up with Christian Siriano to create a marvellous tuxedo-gown hybrid.

“It was a risky move that avoided stunt status through Christian’s precise execution and Billy’s defiant delivery,” Dijanna praises.

However, whilst truly spectacular and bold, Billy porter did not make Oscars red carpet history by donning a dress.

According to Dijanna, that accolade belongs to Tim Chappel, who was also a costume designer for the movie Priscilla Queen of the Desert.

Tim donned a skirt to accept his coveted gold statue, however he seemed to fly under the radar when standing next to Lizzy Gardiner’s eye-catching credit card frock.

Once again in 2022, the men of Hollywood were put on notice when Timothée Chalamet made waves baring skin by foregoing the traditional dress shirt in a suit.

After what has felt like decades of men appearing at these prestigious events in a stock standard suit, Timothée made Oscars red carpet history when he bucked gender norms and formality constraints which has possibly shifted men’s red carpet culture for future events.