In 1996, Diana, Princess of Wales ripped apart a designer dress. John Galliano had just been appointed as the head of French fashion house Christian Dior and his first job had been to create a frock for the Princess to wear to the famed Met Gala.
The gown he designed for the Princess was a dramatic departure from her usual look, a very contemporary slinky slip dress, trimmed with lace.
However, when the Princess arrived at Metropolitan Museum in New York with her good friend, magazine editor Liz Tiberris, Galliano was absolutely shocked. The dress he had created for Diana had an interior bustier to make the slip a more modest number.
Unbeknown to him Diana had made some alterations herself. When the designer first saw the Princess he was stunned, telling The Wall Street Journal: "We were like, Oh, my God – she's torn out the corset. It was a reflection of how she was already feeling: liberated."
While the Christina Strambolian black cocktail dress Diana had worn to the opening of the Serpentine Summer Party in 1994 (AKA the Revenge Dress) was far more obviously daring, Diana's look that night for the Met Gala was far more of a bold statement.
Here was the single mother very clearly showing off a new boldness and willingness to take risks. For the then-35-year-old, this was a symbolic moment, heralding the start of her new life as an independent woman and her intention to live a much more international existence. It was thrilling.
Which is why, if Meghan does roll up, she will be very much nailing her colours to the celebrity mast and will telegraph where she sees her future, that is, wedged firmly in the Hollywood milieu.
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This week, she and husband Harry are set to undertake their final series of events in London as working HRHs, with the official "divorce" set to take place on March 31. What comes next for the pair remains an absolute unknown.
The challenge now for the duo is to somehow find a way to maintain a certain dignity and shore up their philanthropic standing while also contending with the hard scrabble reality of creating a pipeline of high-paying gigs (especially if they end up being personally lumped with having to pay for their own security, a bill which one estimate has put at an eye-watering $39 million-a-year.)
The indications thus far is that this may prove quite challenging.
While they had previously been expected to set up a charitable foundation, in February announced that instead they would be establishing a "non-profit entity" and planned "to develop a new way to effect change".
Now, according to a new report in The Sun today, Diana's daughter-in-law Meghan, Duchess of Sussex might be following in her footsteps, with the UK newspaper stating that she is set to attend this year's bash.
And if she did, I think it would be a huge mistake.
The parallels between the two women at this point in their lives is intriguing. Like Diana, Meghan bought a radical approach to a fusty 1000-year-old institution before finding her ambitions and identity stifled by royal life.
Like Diana when she ascended the famous Metropolitan Museum steps in 1996, Meghan is on the precipice of starting a new, post-royal life.
Like Diana, Meghan (and Harry) seem to hunger for the freedom of life outside The Firm and the opportunity to craft and a fashion an existence of their own making.
However, unlike when Diana attended the Met Gala nearly 25 years ago, Meghan's attendance would not be a bold statement of independence but a PR misstep which could be highly damaging. The reason? The actual Gala and the celebrity landscape have changed dramatically since the 90s.
In Diana's day, the Gala was the pinnacle of high-society glamour, an intoxicating nexus of money and exquisite taste and it was a night that brought together the haute couture-loving, subtly-facelifted New York grand dames with the upper echelons of the style world. That has dramatically changed in the intervening years.
These days the famed party, always held on the first Monday in May, has become a cavalcade of Kardashians and celebs squeezed into ever more outlandish outfits and the whole thing is far more of a global marketing exercise than an elegant evening.
The gala has become an event that reflects our era, an attention-seeking, pop culture-soaked extravaganza seemingly designed for the Instagram age.
In January, a video emerged of Harry seemingly touting for work for Meghan with then Disney boss Bob Iger, while in February, they attended a JP Morgan conference in Miami, an event for which it has been alleged they were paid a six or seven-figure sum.
All of which creates the unfortunate impression that, right now, the couple is more focused on bolstering their bank account (and standing with Beyonce) than benevolently making the world a better place.
If the Duchess did attend the Gala in May, that would lend more credence, rightly or wrongly, to that perception.
Like Diana, Meghan is a person clearly driven by an innate sense of purpose and has a clear view on what she wants the next chapter of her life to look like. But, there is no getting away from the fact that when Diana went to the Met Gala, it was a declaration of independence.
And if Meghan goes, it would be a declaration that she and Harry are now open for business.
Daniela Elser is a royal expert and writer with 15 years experience working with a number of Australia's leading media titles.