Anna Wintour has revealed her proudest achievement in her 36 years as editor-in-chief of Vogue. 

The British editor, 74, reflected on her early career at the US fashion bible in Disney+’s new documentary series In Vogue: The 90s, which is available to stream on Friday.

After being made editor-in-chief in 1988, Anna – who had lost a number of friends to AIDS – organised the ‘7th on Sale’ charity fundraiser.

During the four-day event, over 100 designers – including Ralph Lauren, Michael Kors and Donna Karan – donated $20m worth of goods, which were then sold for a fraction of their retail price to raise money for the New York City AIDS Fund.

The mother-of-two explained: ‘The fashion community was one of the hardest hit [by the AIDS epidemic]. So many people that we cared deeply about were being affected.

Pictured: Vogue editor Anna Wintour, 74, at Marc Jacobs’ AW24 show in New York in July. The editor has contributed to a new Disney+ series

‘It’s hard to think about this now but there really was trepidation about talking about HIV or the illness itself. It was just not discussed.’

However, the Vogue editor says she was motivated to act when she lost her close friend Alan Buchsbaum – who was an architect and designer – to the illness in 1987.

She explained: ‘[He was] one of the first people I met when I moved to New York [in 1976] and we spent a lot of time with him.’

The editor appeared visibly emotional as she detailed how Alan told her ex-husband David Shaffer that not being able to see her son Charles grow up was his ‘biggest regret’.

Following the loss of Alan, Anna says there was an ‘urgent need’ to raise awareness as well as money.

She added: ‘So it was not a question of, “should we do this?” It was a question of, “how should we do it? How quickly? How can we make a statement that will not only reach our community but the world?”‘

Anna said the idea behind the 7th on Sale event was to create a ‘street fair’, where designers would sell their clothes and accessories at their respective booths.

Reflecting on his experience of the event, Michael Kors said: ‘Sometimes in fashion, you feel what you do is light or frothy.

Anna Wintour pictured with French fashion photographer Patrick Demarchelier at the Seventh on Sale AIDS benefit in July 1990

Photographer Steven Meisel, director Herb Ritts, and supermodel Christy Turlington attend the Seventh on Sale charity event in New York in 1990

Fashion designers Bill Blass & Donna Karan, trying on a Blass evening dress, at 7th Ave on Sale AIDS benefit

David Bowie and supermodel Iman arrive at the 7th On Sale AIDS Benefit at the Lexington Avenue Armory in Manhattan

‘But in this instance, we thought: “Wow, what we do actually can make a difference.”‘ 

At the time, Anna told a TV reporter that the event had raised over $1m before they had even sold an item.

Looking back on the event 34 years later, Anna said: ‘7th on Sale – as small as it was – really changed the conversation.’

Despite being the chairwoman of the Met Gala for the past 29 years, Anna says this AIDS fundraiser is her real career highlighted. 

The Vogue editor added: ‘When I look back at my career, honestly I have to say, it’s the initiative that I am the proudest of.’ 

Elsewhere in the documentary, Jean Paul Gaultier revealed his boyfriend died of AIDS while Tom Ford said he lost seven friends to the illness.

Pictured: Anna Wintour with the late Karl Largerfeld at the Seventh on Sale event in New York in 1990

The Vogue editor says she was motivated to act when she lost her close friend Alan Buchsbaum – who was an architect and designer – to the illness in 1987

Before she moved to Vogue in 1981, Anna had previously worked at Harpers & Queen in London and Harper’s Bazaar in America.

She said of her promotion to the head of Vogue: ‘Conde Nast [appointed me] because it was time for change.

‘Under the previous leadership, every cover of Vogue looked all the same […] sometimes you just need to tear everything up and start over.’

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Admitting that she had ‘no plan’, Anna said she set about finding a team of ‘brilliantly creative people’ to work with as she opened up about her career at the fashion bible.

While on board a flight from London to New York in 1989, Anna says she got talking to a ‘very conservative gentleman’, who praised the magazine for previous issues featuring Audrey Hepburn and Grace Kelly.

After he joked that Madonna would never appear on their front page, the editor said she had a ‘lightbulb’ moment and became set on featuring the ‘controversial’ pop star.

Earlier this week, Lewis Hamilton revealed he ‘received fashion advice’ from Anna as the pair watched the US Open final together in New York.

The British racing driver, 39, stepped out on Saturday to watch Jessica Pegula of the U.S. take on Belarus’ Aryna Sabalenka in the final. 

Anna and Lewis said greeted one another as they arrived for a day of tennis, before the fashion guru gave the F1 star some clothing tips, The Sun said. 

The pair, who are tennis fans and attended Wimbledon together in 2018, were seen beaming as they greeted each other and chatted in the stands.