The red carpet may be temporarily rolled up, but Tinseltown’s style rebels are secretly plotting their next fashion insurrection. As A-listers rummage through Hollywood’s fashion archives, the upcoming Met Gala prompts a revisit to the ceremony’s most jaw-dropping and provocative fashion moments—a trip down memory lane where fashion risks were taken, boundaries were pushed, and controversy reigned supreme. Which fashion flubs made the cut? Who dared to bare all? And which sartorial sacrifices sparked outrage and admiration?

From daring exposures to audacious experiments, here are 15 times celebrities committed sartorial sins that left the world aghast, bewildered, and dare we say, utterly fascinated. 

Kim Kardashian broke the Internet during the Met Gala 2022 in a sheer sparkly gown originally belonging to Marilyn Monroe. Kardashian reportedly borrowed the dress from Ripley’s Believe It or Not!, following its purchase from Julien’s Auction in 2016 for a staggering $4.81 million.

Kardashian's quest to squeeze into the gown was a tale of torture and tantalization, proving some styles are more suffocating than sophisticated. But as she slipped into the historic number, she also slipped in the eyes of critics who cried foul over her decision to wear a dress that was more relic than runway-ready.

Rihanna stepped up to Met Gala 2018’s theme, Heavenly Bodies: Fashion and Catholic Imagination, in a papal miter, a ceremonial headpiece of bishops, sporting Maison Margiela Artisanal’s strapless mini dress with a floor-length detailed collared robe.

Despite hitting the sartorial bullseye with the theme, the backlash was brutal, with many translating the fashion iteration as a disrespect to the religion.

Alexandria Ocasio-Cortez made a Met Gala debut in 2021 no sartorial shuffles can ever overlook. She walked the red carpet in a white Brother Vellies gown with a slogan, “Tax The Rich,” emboldened in red across her back.

Cortez’s crimson carpet coup intended to spark conversations around “fairness and equity,” as Ocasio-Cortez told reporters about the inspiration behind the statement at the Gala. But it was her daring backdrop that left the viewers scrambling for shelter.

Taylor Swift’s style has long been the darling of Pinterest, but at the 2016 Met Gala, she made a daring departure from her signature sweet aesthetic. Gone were the girl-next-door giggles and crimson kisses.

Instead, Swift stormed the red carpet in a rebellious goth-inspired Louis Vuitton ensemble, complete with a bold, bleach-blonde bob.

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The pièce de résistance, however, was the dark, dramatic lip color that sealed her transformation from sweetheart to edgy, igniting a firestorm of criticism and praise in equal measure.

Sarah Jessica Parker has been worshipped as the sartorial guru since S-- and the City. However, her take on 2015’s Met Gala theme of China: Through the Looking Glass sparked relentless criticism.

Parker donned an H&M gown of her own design with a Philip Treacy headpiece, the latter was slammed for appropriating offensive cultural stereotypes at fashion’s biggest night in Hollywood. 

Met Gala historically capitalizes on extravaganza because anything otherwise is a rule-breaker. But when Rihanna pulled up at the 2015 Met Gala in a voluminous 55-lb Guo Pei gown, covered in so much fur that it spread across the entire staircase felt less.

The red carpet look caused a firestorm of criticism from fur activists since the dress was reportedly made out of fox fur, making her subsequent perfume launch a magnet for protestors (via Dazed.)

Kim Kardashian’s 2021 Met Gala look was a real cloak and dagger affair. But instead of invisibility, she opted for an all-black Balenciaga ensemble that made her almost invisible to fashion sense.

The Internet was left scratching its head, wondering if it resembled a little too close to a giant trash bag, and the memes and trolls had a field day with her look becoming the fashion equivalent of a Horcrux.

The Jenner sisters, like the Kardashians, are famous for their fashion genius. However, when Kendall Jenner walked the 2017 Met Gala carpet in a barely there La Perla sheer floor-length gown, controversy followed suit.

Though sheer dominance of fashion extravaganza is not a trend she began, it sparked quite the chaos with critics drawing comparisons to Rose McGowan’s back-revealing dress.

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Although fashion resurrections are well-received, one label fashionistas never want to flaunt is of a copycat.

Jaden Smith’s Met Gala 2017 look was a hair-raising experience, literally! The icon brought his dreadlocks along for the ride as an accessory because who needs a clutch when you have a cascade of cut-out tresses?

Paired with Louis Vuitton boots, Smith’s overall vibe was less fashion and high maintenance—well, until it was not. Smith’s look at least launched a thousand what-was-he-thinking, and safe to say, the meme palette has still not gone stale. 

Ye, formerly Kanye West, could be a fashion god. But his knack for eccentrics once had him outrageously defying the Manus x Machina: Fashion in an Age of Technology Met Gala in 2016.

The ‘Vultures’ rapper stepped out in a custom Balmain jacket, a Fear of God distressed jeans, and just when the fashion critics thought that was enough, his eyes lit up like a blue candy with his contacts matching his denim color. 

The 2023 Met Gala’s theme, Karl Lagerfeld: A Line of Beauty, saw a feline excursion on the red carpet. But the most jaw-dropping of all was Jared Leto’s literal animated transformation into one in a catsuit, resembling the late designer’s beloved cat, Choupette.

While the social media was already abuzz, both Penelope Disick and North West went all out, calling it out as “cringe" in a 2023 episode of The Kardashians.   

Billie Eilish brutally butchered her bad-girl, baggy brand in 2021, trading it for Barbie-esque, blonde bombshell makeover at her Met Gala debut. The Oscar de la Renta peach tulle gown was a sugar-coated sledgehammer to her street-style stalwarts, leaving some fans betrayed and others bewitched.

Love it or loathe it, it was a delicious demolition of her former fashion persona.

Many defy the rules in Hollywood and land in history. But which side they touchdown on could be up for debate. Karlie Kloss’s thematic departure for seemingly overlooking the 2019 Met Gala theme of Camp: Notes on Fashion saw her catching flak for opting for a gold metallic minidress with puffy black sleeves.

In a statement for Vogue’s video series Life in Looks in 2023, however, she admitted that she did “deserve” the criticism without an excuse.

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Yet, little did she know, in the years to come, she would be considered the camp queen of all time and it sounds like, Kloss' couture redemption has no expiry date.

Priyanka Chopra’s Met Gala debut in 2017 was more of a coat-astrophe. The Bollywood bombshell’s bespoke Ralph Lauren trench coat dress was a dress-to-impress, but somehow it left fans wrapped up in laughter.

Chopra herself buttoned up and joined the meme brigade later on, but it was a fashion moment Met Gala’s history will never forget. 

At the 2019 Met Gala, Katy Perry took the theme of Camp to a different level by literally showing up as a human chandelier. The dress was designed by Jeremy Scott for Moschino with a silver Swarovski crystal-clad mini dress and bodice.

If fans, however, thought that was extra, she served a petri dish of hilarity by pulling up like a cheeseburger to end the night. 

For an icon who lives, breathes, and made her empire in fashion, Kim Kardashian sure has landed quite a few times on the wrong side of couture archives. In 2013, she opted for a Met Gala look in a long-sleeved floral gown by Givenchy and soon the meme field ran full with comparisons of it to couch material.

Kardashian, however, is definitely not the only one who has had their fashion reputation hanging by a thread because who knows what couture conflicts await this forthcoming couture season?

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What do you think of these controversial Met Gala looks? Let us know in the comments below!