Joshua Goldman
Joshua Goldman
min read · June 30, 2025 · Entertainment

Inside Vogue: Anna Wintour's Era Under Fire

When it was announced that Anna Wintour would be stepping away from one of her roles at Vogue after a whopping 37 years, the fashion industry was left shocked over the news

The Infamous Anna: A Scandalous Reign

Meet Anna, the queen of controversy and drama, who has left a trail of scandals and surprises throughout her illustrious career. As the editor-in-chief of Vogue and Vanity Fair, Anna has always been known for her sharp tongue and unapologetic attitude, but even she can't escape the wrath of the internet.

Fierce from the Start: Anna's Bullying Past

As the fashion world comes to grips with the news, FEMAIL has recapped Anna's many scandals from over the years

It all began in school, where Anna allegedly bullied her classmates. According to reports, she was known for being cruel and mean-spirited, leaving a lasting impact on those around her. But little did anyone know that this feisty attitude would be the precursor to a life of drama and controversy.

The Marriage that Ended with Scandal

Anna's marriage to David Shaffer ended in 1999, but not before she had allegedly cheated on him with a married millionaire businessman named Shelby Bryan. The scandalous affair made headlines, and Anna's reputation took a hit. But she didn't let it slow her down – instead, she went public with Shelby, and the two were together for nearly two decades.

Former classmates of Anna's previously claimed that her teenage years were marred by petty jealousies and extreme cattiness . She's seen in 1973

Racism Allegations: Anna's Dark Past

In 2020, Anna was accused of racism by 18 black journalists who had worked with her at Vogue. The allegations claimed that she favored employees who were "thin, rich, and white," a charge that left many feeling shocked and betrayed. Anna apologized for using the term "pickaninny" in a memo, but the damage was already done.

Vanity Fair Drama: Mark Guiducci's Appointment

One of the magazine mogul's ex-friends Vivienne Lasky described Anna (seen in 1973) as 'harshly critical and sarcastic,' and claimed she 'made fun of people who weren't' like her

In April, Vanity Fair announced its new editor-in-chief, Mark Guiducci – Anna's daughter Bee's close friend. The decision sparked outrage among staff members who felt he wasn't qualified for the job and was only appointed due to his connection to Anna. The controversy surrounding Mark's appointment has left many questioning Anna's judgment.

The Met Gala Debacle: A Fashion Faux Pas

This year's Met Gala was met with widespread criticism, with many attendees accused of wearing unremarkable outfits. PR expert Sarah Schmidt even called for Anna to step down from hosting the event, stating that she had become "stale" and needed a reboot.

Alex Walker, a highly respected editor at Anna's father's paper, also remembered Anna as an 'absolute monster' who would do and say things just 'to be mean.' Anna is seen in 1972

A Legacy of Controversy: Anna's Impact on Fashion

From her alleged bullying past to her controversial marriage and racist allegations, Anna has left a lasting impact on the fashion industry. Love her or hate her, there's no denying that Anna has always been a force to be reckoned with. But as her reign comes to an end, can she truly leave behind a legacy of respect and admiration?

In conclusion, Anna's life has been a whirlwind of drama, controversy, and scandal. From her bullying past to her racist allegations, she has left a lasting impact on the fashion industry. As we look back on her tumultuous career, one thing is clear: Anna will always be remembered as a queen of controversy.

Over the years, Anna has had a slew of public feuds with big stars and fashion figures, including her former colleague and friend Andre Leon Talley (seen together in 2009)

He unleashed a furious tirade against Anna in his 2020 book, accusing her of ending their friendship because she believed him to be 'too old, too overweight and too uncool'

Andre, who was editor-at-large of Vogue magazine from 1998 to 2013, also claimed that Anna never said anything 'human and sincere' during their many years working together

Back in August 2023, Billy Porter slammed Anna after Vogue featured Harry Styles in a dress on its cover

He added that he had sat down for a chat with Anna months prior focused on inclusivity. He recalled, 'That b***h said to me at the end,

TV personality Tim Gunn also hit out at Anna in his 2010 book, claiming she insisted on being 'carried down' a set of stairs by her bodyguards while leaving a fashion show

Over the years, Anna (seen in 2013) has earned the nickname 'The Ice Queen' due to her emotionless demeanor and fierce determination to ensure each Vogue issue was 'perfect'

One reporter who worked in the same building as Vogue in the early 2000s said that crossing paths with her was so scary it would 'immobilize her.' She's seen in 2011

Anna has long been described by pals as a 'perfectionist' and it was said she was involved in every single detail about every single Vogue issue

In addition, Anna - who has hosted the coveted Met Gala for over 30 years - has raised eyebrows over the alleged measures that she has taken to ensure everything goes well at the event

In 1984, Anna married child psychiatrist David Shaffer (seen in 1991), and together, they welcomed a son named Charles and a daughter named Katherine, now known as Bee

But they split in 1999 after 15 years of marriage, and their breakup was shrouded in scandal. They're seen in 1994

At the time, a whirlwind of reports claimed that her marriage had ended because Anna had cheated on her husband with a married millionaire businessman named Shelby Bryan (seen)

Even so, she and Shelby went public with their romance soon after her marriage to David ended, and they were together for nearly two decades after that. They're seen in 2003

But in October 2020, it was revealed that she and Shelby had quietly gone their separate ways. A source told the Daily Mail at the time that it ended 'because she had grown bored'

In 2020, a group of 18 black journalists who had worked with Anna over the years accused her of favoring employees who are 'thin, rich, and white'

11 of them called for her resignation following cultural appropriation controversies - including outrage over a 2017 Vogue shoot that featured Kendall Jenner wearing fake gold teeth

Anna responded with: 'I strongly believe that the most important thing any of us can do in our work is to provide opportunities for those who may not have had access to them'

This year's Met Gala was brutally blasted online after fans were left unamused by many of the attendees' choice of clothing. Kim Kardashian is seen at the Met Gala

The 2025 theme - Superfine: Tailoring Black Style - presented an opportunity for 'boundary-pushing' looks, but big names such as Kendall Jenner (seen) struggled to stand out

Afterwards, leading PR expert Sarah Schmidt advised Anna to end her three-decade reign and pass on the baton in a bid to introduce 'radical imagination.' Anna is seen at the event

News hit the web earlier this month that Anna had picked her daughter, Bee's close pal Mark Guiducci to run Vanity Fair following a high-profile search for the publication's next leader

Afterwards, an insider alleged to the Daily Mail the decision had sparked immense outrage in the company , claiming that many Vanity Fair staffers felt like Guiducci was 'not qualified'

His friendship with Anna's daughter has spanned years and the two have been photographed together frequently, often at high-profile parties

'Anna has tried to bring Bee more into the fold,' the source claimed. 'The thinking is that having Mark oversee Vanity Fair [will give] Bee an outlet to host parties and be part of the Vanity Fair'