Unveiling the Royal Inspiration: How Anna Wintour Transformed the Met Gala into Fashion’s Premier Event

Every year, the Met Gala stands as the pinnacle of the fashion world, drawing in celebrities and influencers from every corner. But what fuels this spectacular event’s enduring allure? One insider suggests it’s none other than Princess Diana who played a pivotal role.

Anna Wintour, Vogue’s Global Editorial Director and Condé Nast’s Chief Content Officer, has been the driving force behind the transformation of what was once the Costume Institute ball at the Metropolitan Museum of Art. Under her leadership since 1995, it has evolved from a simple society dinner into an unmissable occasion on the fashion calendar.

Behind this transformation lies a compelling narrative of rivalry. Wintour and the late Elizabeth Tilberis, former editor of Harper’s Bazaar, were engaged in a fierce competition to elevate their respective magazines. This competition reached its peak in 1996 when Tilberis brought Princess Diana as her guest to the Met Gala.

Filipa Fino, who served as the senior accessories director at American Vogue and worked closely with Wintour for seven years, recounts the intensity of this rivalry. Both editors were determined to outshine each other, vying to make their publications the ultimate authority in fashion.

The stakes were raised when Tilberis not only secured Diana’s attendance at the gala but also featured her on the cover of Harper’s Bazaar’s September 1997 issue. This bold move marked a significant triumph for Tilberis and a setback for Wintour.

For Wintour, who felt she should have been the one to escort the princess, this incident ignited an unwavering dedication to the Met Gala. According to Fino, it was this turning point that spurred Wintour’s relentless commitment to making the gala an unparalleled spectacle.

‘The princess died and it never happened and Anna had no way of getting redemption,’ Fino told The Times.

‘This seed of Anna never being able to host Princess Diana at the Met, and her vision of what it should be like – worthy of a princess – is what drove her from 1996 to today. She took on the Costume Institute Ball as her own personal project.’

‘She’s p***** off at God. She’s p***** off at time. She’s p***** off with history, which had Diana die before she got her a cover.’

When Diana attended the Met Gala on December 9, 1996, it was four months after the divorce papers had been signed and just eight months before her death.

She sported a £10,000 midnight-blue dress, trimmed with black lace and worn under a matching velvet opera coat.

It was also a fashion coup because Diana was the first person to wear a gown by Dior’s new designer, the enfant terrible John Galliano, from his highly anticipated first haute couture show.

She teamed it with her sapphire choker set in a triple strand of pearls and her Lady Dior bag, originally called the ‘Chouchou’, and renamed in her honour.

She had been given her first ‘Chouchou’ bag on a 1995 visit to Paris by the then-first lady, Madame Bernadette Chirac, and it became a firm favourite. She ordered it in blue the following year to ‘match her eyes’.

Galliano and his team travelled from Paris to London three times for fittings, making their last visit on November 28, the designer’s 35th birthday. He arrived at Kensington Palace to find that the princess had organised a cake and champagne.

But the dress evoked mixed feelings. Fashion editor Hilary Alexander described it as ‘The most important dress since Liz Hurley wore her safety-pinned Versace’. 

‘The whole idea of wearing a petticoat in public is new,’ she wrote in the Daily Telegraph.

‘We have seen actresses and starlets wearing underwear as outerwear, but for a princess to do it at a formal occasion is a different matter.

‘It is a very sensual rather than overly sexy dress, and it is a million miles away from the more formal outfits she usually picks.

‘It represents a new kind of royal dressing. By wearing the dress on such an important occasion, she is also paying a long-overdue homage to Galliano.’

Pictured: Elizabeth Tilberis, former editor of Harper’s Bazaar magazine, is shown seated at an office desk in 1992

Fashion critic Brenda Polan, however, was less of a fan: ‘It was not so much haute couture as Oh! Couture,’ she wrote, in the Daily Mail.

‘The problem, and there is no delicate way of saying this, is that it looked like she had accidentally stepped out in her nightie, which meant, of course, that she wasn’t wearing a bra.’

However, in a 2018 interview, Galliano revealed that Diana had chosen to remove the interior bustier. ‘It was a reflection of how she was already feeling,’ he told the Wall Street Journal Magazine. ‘Liberated.’

Guests at New York’s party of the year included designers Calvin Klein and Christian Lacroix, models Linda Evangelista, Christy Turlington, Iman and photographer Patrick Demarchelier.

After sipping champagne and chatting with designers Vera Wang, Oscar de la Renta, Calvin Klein and Bill Blass, Diana, seated between Tilberis and Galliano, dined on sea bass, veal and tarte tatin.

But she slipped away before midnight, whisked in a stretch limo back to the plush Carlyle Hotel as the dancing was set to begin, missing the furore on the dance floor as guests smashed glasses and split champagne.

‘It was a zoo, and I guess that maybe they didn’t want to put her through it,’ said Mica Traynor, a fashion designer. ‘But I didn’t feel she was actually here. I just wanted to see her dance once, but no luck.’

‘People wanted to just look at her,’ added debutante Crickett Richards. ‘They paid to see her, and, to all intents and purposes, she did not show up. It’s a shame. She is so beautiful. I think she could have tried a little harder.’

However, Bianca Jagger said: ‘I don’t think she ever intended to stay long, but I know she enjoyed herself. She looked marvellous.’