Cher in Bob Mackie, 1974 - Cher has made a career out of being ahead of the curve, and nailed the ethereal sheer dressing trend decades before it was popularised. For the 1974 Met, she wore a gown by her long-time costume collaborator Bob Mackie, made of the then-outlawed soufflé fabric that was sprayed to fit her like a second skin. Though one can only imagine how stirring this dress would’ve been by 1974’s standards, it exemplifies Cher’s ability to create conversation through the clothes she wears, and push the envelope for experimenters to follow in her footsteps.

Princess Diana in Dior, 1996 - While the Met draws high-profile guests from all corners of celebrity, spotting a royal in attendance is a rarer occurrence. In 1996, Princess Diana famously attended (photographed above with editor Liz Tilberis), and wore a deep-blue camisole dress with lace details—designed by a then-little known John Galliano. In her later years, the Princess of Wales was known for her embrace of avant-garde designers and striking silhouettes, and this ensemble was no exception, working like catnip for photographers on the night.

Liv Tyler and Stella McCartney, 1999 - The ‘Rock Style’ theme at the 1999 Met Gala left attendees wondering how to nail the brief, but for Liv Tyler and Stella McCartney—daughters of iconic rock-stars Steven Tyler and Paul McCartney—it was light work. Of their custom ‘Rock Royalty’ t-shirts, which McCartney had printed the morning of the Met, the fashion designer said, “I didn’t come at it intentionally to be rebellious at all. I didn’t know what people wore.” She added, “In this day and age, people would really plan it and overthink it intentionally to get attention in the media. And we really didn’t, and that is what’s so lovely about it.”

Kim Kardashian in Jean Louis, 2022 - There’s a reason Kim Kardashian’s dress from 2022 looks familiar: it was originally worn by Marilyn Monroe to sing ‘Happy Birthday’ to President John F. Kennedy in 1962, taken out of a museum on loan for the night. The dress was only on Kardashian for a handful of minutes; once inside the gala, she changed into a different outfit to prevent damaging the historic piece. Naturally, social media was alight with conversations about whether the dress should’ve been worn at all, but if there’s any outfit that exemplifies the Met Gala’s reputation as the ‘Fashion Olympics’, it’s this.

Taylor Swift in Louis Vuitton, 2016 - The 2016 gala marked a new beginning for Taylor Swift’s style; the performer channelled her look on American Vogue’s then-newly released May 2016 cover with a peroxide-blonde chopped bob and Louis Vuitton mini dress. Fans were divided on the look, but the edgier vibe served Swift well—carrying over into her darker Reputation album, which was released in 2017.

Karlie Kloss in Dapper Dan x Gucci, 2019 - Supermodel Karlie Kloss admitted to having no idea that her gold mini-dress for the 2019 Met Gala would cause a stir, as some deemed it unfit for the high-level glamour we usually expect from the Met. Earlier in the night, Kloss teased her look with a selfie with the caption “Looking camp right in the eye”—a tie-in to the theme, which has since reached meme infamy online. In a video posted later on her YouTube channel, Kloss said, “I could feel the [negative] reaction literally from when I walked onto the red carpet.”

Katy Perry in Versace, 2018 - Always one to take the event’s theme to the next level, Katy Perry ruffled feathers (quite literally) with this angelic Versace number, which was so tall she could barely get through the door.

Kim Kardashian West in Vivienne Westwood, 2017 - Though she’s known for bringing unmissable glamour to the Met, the boldest thing about Kim Kardashian’s 2017 Met Gala dress was its simplicity. Her Vivienne Westwood dress was worn without jewellery, as part of her sartorial response to being robbed at gunpoint in Paris in late 2016; it’s believed Kardashian was targeted for her displays of wealth on social media, including her Lorraine Schwartz engagement ring, which was taken by thieves. While the event was traumatic, Kardashian later recounted that the robbery was a transformative moment in her life, and that it made her “a different person”.

Kendall Jenner in La Perla, 2017 - The allure of a sheer ‘naked’ dress has been utilised on the Met red carpet by everyone from Beyoncé to Bella Hadid, but Kendall Jenner took it to another level in this slinky, spellbinding custom number by lingerie brand La Perla, worn with matching Christian Louboutin pumps.

Pharrell and Helen Lasichanh in Comme des Garçons, 2017 - Couple style has never been as bold as when Pharrell arrived at the 2017 Met in jeans and Doc Martens, while his wife, model Helen Lasichanh, embodied Lego-chic in this number from Comme des Garçons’ autumn/winter ’17/’18 collection.

Sarah Jessica Parker in Monse, 2016 - Those who criticised Sarah Jessica Parker’s ensemble at the 2016 technology-themed Met Gala were served a slice of humble pie by the actress herself. When one blogger wrote on Instagram that Parker’s Monse number didn’t do justice to the theme, the Sex and the City star commented: “Always welcome thoughts but I’m a stickler for the theme and pay close attention to what it means. Every year with great consideration, research and conviction. The understanding of man and machine, how they intersect, when and why is what we considered. Perhaps you weren’t aware of the technology used in the details and embellishments of the design. Or perhaps you simply didn’t like what I wore which is completely fine but you can’t accuse me of not paying close attention and adhering to the theme. With respect and warmest regards, sj.”

Rihanna in Guo Pei, 2015 - Though this look by Chinese couturier Guo Pei is enshrined in Met Gala history, the fox-fur edges struck a chord with anti-fur activists, some of whom found it irresponsible for Rihanna to promote fur use.

Grimes in Iris van Herpen, 2021 - Who else but Grimes could bring a sword to the Met, and make it work? Iris van Herpen designed the ‘Genesis’ performer’s futuristic dress, while Marc Jacobs’ ’70s punk Kiki boots boosted her to new heights.

Kim Petras in Collina Strada, 2021 - If you were asked to define ‘horsing around’ at the Met, the strikingly realistic equine dress worn by Kim Petras at the 2021 Gala would be a perfect fit. The insouciant number was created by New York label Collina Strada, modelled off its spring/summer ’22 collection, which featured life-size animal heads and objects built into the clothes. Petras’ long hair—a ‘pony tail’ in every sense—completed the visual.

Jaden Smith in Louis Vuitton, 2017 - Comme des Garçons designer Rei Kawakubo, the thematic subject of the 2017 Met Gala, is famous for her abstract, deconstructed silhouettes—which made the night’s theme a particularly difficult one to nail. However, what could be considered more ‘deconstructed’ than carrying your own chopped-off hair in your hand, á la Jaden Smith?

Frank Ocean in Prada, 2019 - Where many stars used the 2019 ‘Camp’-themed Met Gala as an excuse to dress opulently, Frank Ocean attended in a very toned-down, albeit still chic, look from Prada. If it was his intention to fly under the radar, it almost didn’t work—his outfit still garnered plenty of attention, mostly for being so unexpected. In a perfectly meta turn, Ocean pulled out his own camera at points on the red carpet, taking film pictures of the photographers.

Timothée Chalamet in Haider Ackermann, 2021 - 2021’s ‘In America’ theme saw attendees channel US-centric fashion staples in their own ways, and Timothée Chalamet, a co-chair of the event, was one of the night’s most talked-about. His decision to pair a satin Haider Ackermann blazer with Converse sneakers was an effortless embodiment of the high-low look, despite some decrying the sneakers for being ‘too casual’.

Bella Hadid, 2017 - Eschewing the idea of a gown or long train, Bella Hadid was pure vixen fantasy in this catsuit, with sheer elements and a cut that left her whole back on display as she slinked up the steps.