The best ever Met Gala looks, from Princess Diana to Rihanna

The First Monday in May is fast approaching, which means one thing: The Met Gala is mere days away.

Also known as the Costume Institute Benefit, the charity event is held in New York’s Metropolitan Museum of Art to support their costume department. Each year, it coincides with the opening of a new spring fashion exhibition, which in turn dictates the dress code. This year’s show is Karl Lagerfeld: A Line Of Beauty, looking back and the life and legacy of the great designer – so expect plenty of Chanel, riffs on tweed, and perhaps a few icy-white pony tails.

What is now one of the biggest international events of the year began as a simple high society dinner in 1948. The legendary former US Vogue Editor Diana Vreeland then joined the board in 1972 and blasted it into the celebrity sphere before Anna Wintour, Vogue’s current Editor-in-Chief, took the reins in 1995 and secured its place as the fashion industry’s Oscars. From this point on, countless memorable looks have made their way up the inafmous Met steps.

In 1996, Princess Diana caused a scadal when she arrived in a blue satin slip dress by Dior. She was, undoubtedly, belle of the ball. As Bob Morris reported in the New York Times that year: “In a midnight blue and black lace gown by John Galliano (the newly appointed designer for the House of Dior), she went into dinner in the museum’s restaurant with Liz Tilberis, the editor in chief of Harper’s Bazaar. The rest of the guests, including Calvin Klein, Bill Blass, Madame Jacques Chirac and Christy Turlington (whose face was the model for the Costume Institute’s mannequins), followed like bedazzled serfs.” It set the night up as the newsworthy display of new fashions that it remains today.

1999 was infamous year Stella McCartney (daughter of Beatle Paul McCartney) arrived arm in arm with Liv Tyler (daughter of Aerosmith’s Steven Tyler), and the pair wore matching asymmetric t-shirts, appropriately reading Rock Royalty.

Sarah Jessica Parker, a New Yorker and long-time Met enthusiast, had her greatest look made by the late Alexander McQueen for the 2006 ball, when the theme was AngloMania: Tradition and Transgression in British Fashion. The pair entered hand in hand, wearing swathes of matching tartan print; him in a kilt, her in a sliced open tulle frock. Since, the Sex and The City star has spoken about the experience, telling Vogue “Like everybody else, I was in love with him. I have every pin he dropped from his mouth in my possession still. I have everything he cut off in my possession still. I have things that seem like nothing, from every fitting I ever did with him in my possession.”

In 2011, the exhibition was Alexander McQueen: Savage Beauty, devoted to the late designer but controversial due to its proximity to his suicide in 2010. The show was to be a huge success, however, and went on to be a blockbuster exhibtion at the Victoria and Albert Musuem as well. On the night, many guests took the opportunity to put his designs in motion, led by SJP, Naomi Campbell and Coco Rocha.

2015 was a particularly well documented year thanks to The First Monday in May documentary, and Rihanna made a clear bid to steal the show. The singer took to the ruby carpeted steps in a spellbinding golden embroidered gown by Chinese designer Guo Pei, which featured a three metre long train trimmed in fox fur, weighing 25 kilograms. It was bang on theme for the China: Through the Looking Glass exhibition, and you would hope so: it took a staggering 6000 hours to make.

Heavenly Bodies: Fashion and the Catholic Imagination, in 2018, saw many take the theme to new levels, as they doubled down on religious. That meant Katy Perry in huge Versace angel wings, Rihanna in a pearl encrusted Pope look by John Galliano for Margiela, and Madonna - who performed later in the vening - wearing gothic black Jean Paul Gaultier.

Camp was the word on everyone’s lips in 2019. As red carpets go, the Met is about as camp as it gets anyway – so attendees had to think big to stand out. That they did. Lady Gaga treated watchers on to four individual looks, designed by Brandon Maxwell, Jared Leto carried a life-like wax replica of his own severed head, and Katy Perry was a human chandelier, designed by Jeremy Scott for Moschino.

The pandemic meant 2020 was the Met that never was, but things sprung back to action with a posponed September date for 2021’s Gala. It was defined by Kim Kardashian in a face covering t-shirt by Balenciaga, Rihanna and A$AP Rocky arriving in sculptural duvet looks, and Iman in a gilded gold look by Harris Reed.

That takes us up to last year, which was themed In America: An Anthology of Fashion, and made way for a host of all-American statements. The headlines were shared, again, by Kim Kardashian who borrowed Marilyn Monroe’s 1962 dress worn to wore to serenade President John F Kennedy (and consequently slammed for, as many deemed it to be a museum artefact), and Blake Lively, who mesmerised onlookers with her colour changing glowing orange to bright turquoise Versace gown, which was an ode to the Statue of Liberty.

If the years have proven anything, it is that it is impossible to guess who will turn up or what jaw-dropping frock they have picked out to wear. 2023’s installment - coming right up.

Scroll through the gallery above to see the best Met Gala fashion moments of all time.