New documentary The First Monday In May charts the ever-fashionable story of the Met Gala. Rebecca Gonsalves examines the most sartorial social event of the year

To us Brits, the first Monday in May is a significant date – as the first bank holiday of the summer, it is to be spent in a pub garden, having a nosy around a country estate or trying not to bicker in the garden centre. It is tradition, and long may it continue. But in recent years, this special day has become inextricably linked with an altogether more fabulous event across the Atlantic, namely the Met Gala, the annual fundraiser for New York’s Metropolitan Museum of Art’s Costume Institute.

Arguably the fashion world’s most important social event, the Met Gala doesn’t disappoint where it matters – on the red carpet – which has provided some of the most memorable fashion moments of recent years. Little wonder: the event is overseen by Anna Wintour, editor-in-chief of American Vogue and co-host of the Met Gala since 1999. She is, undoubtedly, the fashion world’s finest party planner.

And Wintour, whose exacting standards and no-nonsense demeanour were chronicled in 2009’s The September Issue, is once again the focus of the camera lens. Last year, film-maker Andrew Rossi was granted unprecedented access to the Met Gala: the night itself and the months of meticulous planning that go into it. His resulting film, The First Monday In May, documents the power struggles and political manoeuvres that go into both the gala and the fashion exhibition that it opens, on this occasion China: Through The Looking Glass.

“Anna is in no way some capricious devil who wears Prada,” says Rossi, referring to that other infamous, albeit fictionalised, portrayal of Wintour on the big screen. But those hoping for more of The September Issue’s tense, bordering on hostile, conversations won’t be disappointed; as Rossi diplomatically puts it, “[Wintour] is not conflict averse and not afraid to challenge any of the people that she works with. She has high, and clear, standards.”

We learn in the film that she vets every single detail of the event, from the floral arrangement to the guest list and even what – or rather who – many of the guests will be wearing. The latter is perhaps the most important element of all: the Met Gala has been dubbed the fashion industry’s Oscars, but where the Oscars’ red carpet has become increasingly sanitised and safe, the Met’s is a breeding ground for experimental design.

Take the robe by Chinese designer Guo Pei that Rihanna wore for the 2015 gala: canary yellow and with a seemingly endless train, it’s the gown that launched a thousand omelette memes. Or Madonna’s controversial interpretation of this year’s ‘Manus x Machina’ theme – black Givenchy lace, with sheer panels over her breasts and buttocks, a fashion statement if ever there was one. Designers seem to approach it in the same way they do couture, relishing the ‘costume’ part of the Costume Institute.

As well as providing a behind-the-scenes view, Rossi was keen to explore the debate over fashion as a legitimate art form, as well as the controversy of a Chinese fashion exhibition from a western perspective. “I wasn’t interested in making a movie about party planning,” he says.

It might not be the focus of Rossi’s film, but the planning process provides some of the most compelling scenes, many of which are stolen by Wintour’s dry wit. Of one prospective guest, she asks: “Can he not be on his cell phone the entire time?” Sadly for viewers, the name of the guest is censored – as is exactly how eye-watering Rihanna’s requested performance fee is. A later scene shows the singer dancing on tables performing B*tch Better Have My Money, to an audience including Beyoncé, Cara Delevingne, and Justin Bieber – a testament to Wintour’s negotiating prowess and the mega-wattage of the guest list.

Since Wintour became chairwoman of the Met Gala in 1995, the event has become inextricably linked with her, and in turn American Vogue, but it wasn’t always thus. The gala dates back to 1948, two years after the Costume Institute itself was founded when The Met merged with The Museum of Costume Art. Back then it was a midnight supper held in December for society matrons who paid $50 for the privilege of attending and were treated to “skits, raffles and pageants of models in historical dress”, according to the Costume Institute’s records.

“I remember the Met Ball when it was still held in December,” says André Leon Talley, former contributing editor of American Vogue. He has been attending the ball since 1975, when he worked at Andy Warhol’s Factory, and Diana Vreeland, as special consultant to the Met, was in charge of reviving the institution’s appeal. “It was the winter party before Christmas for New York society. It was a much smaller dinner in those days, about 300 people – very select,” says Talley. In the Seventies there was no red carpet but guests still dressed to impress. “You had a dress of the season and you would debut it at the Met Ball.” Back then New York was a vibrant, experimental place, Warhol was a ball regular, although he wore jeans with his jacket.

“Mrs [Jackie Kennedy] Onassis once attended in a black strapless Valentino,” recalls Talley, never one to forget a devastatingly beautiful dress. Hillary Clinton attended too, in 2001, in a floor-length leopard print gown and even Princess Diana graced the gala with her presence in 1996, in one of newly appointed Dior designer John Galliano’s very first gowns for the house – a navy sheath dress trimmed with lace. It’s fitting that royalty and political royalty have attended, as the event so closely resembles a modern-day royal court, presided over by Wintour. No doubt Kate Middleton and Michelle Obama are top of her 2017 wishlist.

Today, the guest list has almost doubled in size, with over 600 invitees, although it remains an event for the elite: tickets reportedly cost £23,000 each, with a table of 10 coming in at £211,000. But even the wealthiest wannabe can’t just buy their way onto the red carpet: this is strictly an invitation-only affair.

And everybody has to pay their way – even celebrities, according to Talley. Or, more accurately, behemoth fashion brands such as Burberry and Versace buy those tickets and tables, and Vogue helps them to connect with the actresses and models with whom they would like to be aligned in the eyes of the public. “Everyone’s invited to walk on the red carpet,” explains Talley. “Everyone dresses the way they want to dress, or see themselves – there are no strict rules.” That’s how, in recent years, the likes of Kendall Jenner, Kate Upton and Jourdan Dunn have worn Topshop on the red carpet, while H&M is making inroads too. In New York, money doesn’t just talk, it hollers.

But just how much fun can such a formal event actually be? According to Talley, guests are aware that the hallowed halls of the Met call for a certain level of decorum. “I don’t let myself go!” says Talley with mock-outrage. “You’re at a very important party, etiquette is demanded at all times – by me at least.” Perhaps that’s why Gwyneth Paltrow declared the event “unfun” in 2013, stating she’d never attend again.

Wintour, though, hopes guests have fun – especially on the red carpet. “It’s a kind of theatre,” she says. “Fashion can create a dream, create a fantasy.” And, as the film shows, fantasy is what the Met Gala is all about.

The First Monday In May is released nationwide on 30 September

Photography: Rex Features, The New York Times, Eyevine, Landmark Media