From Björk To Timothée Chalamet — 15 Oscars Looks That Pushed The Ceremony’s Dress Code To The Limit

Cher was looking to command “attention” with her Bob Mackie dress at the 1986 ceremony, the designer said in a 2018 interview with The New Yorker — and attention is what she got.

“She was p**sed off because she didn’t get nominated” for her performance in Peter Bogdanovich’s Mask, Mackie divulged to the outlet, before recalling how the black outfit, which exposed her midriff and turned heads with a plumed mohawk headdress, was called “not fashion” at the time.

Now, views regarding Cher in the dress on social media range from “No one dressed like her then,” to “Iconic” and “revolutionary.”

The singer and actress shut down the Oscars in a see-through beaded gown by Bob Mackie in 1998. 

She completed the look with a matching headpiece and choker necklace. 

“I loved her over-the-top get-ups, especially the ones with Bob Mackie,” a fan wrote.

At last year’s Oscars, Julianne Hough wore a flowing, mocha-hued gown from Christian Dior’s Spring 2025 ready-to-wear collection.

The sleeveless design featured a slightly cinched waist for added definition.

However, the fact that the gown came from a ready-to-wear line made it less suited to the formality typically expected at a black-tie event.

A critic sounded off on Reddit: “You can tell it's not for an evening affair.” 

The Icelandic singer, songwriter, and composer arrived at the 2001 Oscars in a swan dress designed by Marjan Pejoski.

The whimsical gown was more of a theatrical costume than traditional eveningwear appropriate for the Oscars, and for that reason, it drew instant ridicule.

TV fashion pundit Steven Cojocaru, per BBC, called the fashion moment “probably the dumbest thing I’ve ever seen.”

“The girl should be put into an asylum,” offered American comedian and actress Joan Rivers.

However, since then, the dress has been regarded as one of the most iconic looks in Oscars history and has become extremely popular among the general population.

“My mom made me this dress for Halloween my sophomore year in college,” a Redditor shared, with another echoing, “I also made a knockoff of the dress for Halloween.”

Rachel Zegler’s first appearance at the Oscars came in 2022, and it remains memorable for several reasons. 

One notable detail audiences recall is that it came after she publicly revealed she had been left off the guest list, despite her film West Side Story being nominated for seven awards.

“IDK y’all, I have tried it all, but it doesn’t seem to be happening,” she said via social media at the time.

Soon after, it was reported that she would attend the show as a presenter.

Zegler went on to make her Oscars debut worth it by walking the red carpet in a Dior creation.

Despite the actress donning a major-label outfit, the sheer finish of her outfit brought her close to breaking the ceremony’s dress code.

“She never fails to slay on the red carpet,” a fan commented regardless.

Barbra Streisand bagged the Academy Award for Best Actress for Funny Girl in 1969, but today, netizens remember her striking fashion that year more than her win.

The actress debated between a “lovely but very conservative” dress and an Arnold Scaasi “pantsuit with plastic sequins,” she told W Magazine in 2016. She ultimately went with the latter option.

“I had no idea that when lights hit the outfit it would become transparent!” she later revealed.

A Redditor, however, refused to believe Streisand, arguing: “It’s not actually see-through. There’s a flesh-colored layer underneath. She knew there was a panel. There’s no way she wouldn’t have known because the portion is very visible.”

Another added, “This outfit was horrible by all means.”

The Australian costume designer caused a stir at the 67th Academy Awards by stepping onto the red carpet in a gown crafted from 253 American Express Gold cards, all carrying her name but missing a digit, hence rendering them invalid.

Using a literal corporate product instead of sticking to prestigious houses such as Dior and Chanel for the night was seen as “tacky” by many.

Besides this detail, the waist-high slit of the dress pushed it far beyond the formal elegance expected under the Oscars dress code.

“I do remember wondering when I first saw this dress how badly it would imprint on the back of her thighs when she sat down,” a Redditor noted about the ensemble.

At the 72nd Oscar Awards in 2000, Trey Parker wore a refined version of Jennifer Lopez’s much-celebrated Versace dress from the 2000 Grammys, while Matt Stone complemented him in a pink gown inspired by the Ralph Lauren piece worn by Gwyneth Paltrow at the previous Oscars.

The South Park creators admitted in several interviews, including Jimmy Kimmel Live!, that they were under the influence of LSD when they walked the red carpet.

“They served,” a Reddit user said about their looks, while another wrote, “They ate.”

“I envy men for being able to do stuff like this without causing too much of a scandal,” a third expressed.

Celine Dion raised eyebrows when she arrived at the 1999 Oscars in a number that expertly blended casual and avant-garde elements.

The singer wore a backward white tuxedo by Dior and completed the look with bedazzled Ray-Bans and a fedora.

The look, which landed Dion on many ‘worst-dressed at Oscars’ lists, has remained a fan favorite.

“I remember thinking she was just so cool when I first saw it in my Teen Vogue,” a Redditor recalled, while another added, “The suit lives rent-free in my head.”

Demi Moore did not care much about wearing a high-end fashion brand at the 1989 Oscars either.

That year, the actress donned a hybrid dress-bodysuit that she fashioned herself out of spandex bike shorts, a corset, and metallic floral-print fabric.

Moore’s style, repeatedly called “worse” by publications like Women’s Wear Daily and Grazia, draws similar reactions on Reddit, with one user recently labeling it “hideous” and another seeing it as “peak ugly.”

Blair arrived at the 2002 Academy Awards in a red tassel dress by Versace that Time magazine described as an “incomplete crochet project” in 2011. 

Milan-based NSS Magazine, meanwhile, compared the design to a “fluttering Vileda mop.”

“Literally the worst,” a netizen agreeing with these publications said.

Edy Williams did not defy the black-tie dress code of the Oscars by a small margin in 1986.

Instead of the expected couture, the He**hole actress wore a showgirl-like outfit to the soirée, consisting of a tiny white thong and strategically placed pearls that ran from the top of her body down to her waist.

“The dress must have driven the censors crazy back then,” a netizen remarked.

Gwyneth Paltrow pushed the boundaries of the Oscars dress code in 2002 by stepping onto the red carpet in a gothic gown crafted by Alexander McQueen.

While the bottom half of the dress featured a black floor-length skirt, the top half consisted of a figure-hugging sheer bodice.

“She was ahead of her time,” a netizen said in the piece’s favor, despite Paltrow herself expressing in a 2013 Q&A posted on her wellness and lifestyle brand Goop that she “should have worn a br*” to make it more modest and in line with the elegance that the Academy demands.

Sacha Baron Cohen arrived at the 2012 Oscars in character, dressed as Admiral General Aladeen, a Middle Eastern leader from his film The Di*tator.

The British comedian also carried an urn bearing the image of former North Korean leader Kim Jong-il.

While speaking to Ryan Seacrest, who was covering the red carpet for E!, Cohen poured the contents of the vessel onto his suit, covering him in white powder. Security then escorted him away.

Criticizing both Cohen’s unconventional attire and his stunt, a netizen wrote, “It was nauseating.”

The actor whose ping-pong biopic Marty Supreme is nominated in nine categories, including Best Actor and Best Picture this year, arrived at the 2022 ceremony in a sequined black suit by Louis Vuitton, worn sans shirt.

The look was pulled from Nicolas Ghesquière’s Spring 2022 womenswear collection, allowing Chalamet to convey that design doesn’t have to be bound by gender. 

He paired the two-piece with sleek, patent ankle-length boots and several white-gold rings by Cartier.

While social media users loved the experiment, with one commenting, “He is one of the few men in Hollywood who tries unique and interesting looks,” the outfit stepped outside the bounds of black tie as it put his chest on display in the absence of a shirt — an essential element of a tuxedo.