Back in 1996, the late Royal wore a slinky navy gown with a stylish lace trim by the French designer as she partied with the fashion elite at the Met Gala in New York.
However, it has now been revealed the late Princess almost avoided the dress entirely because she worried it would "embarrass" a teenage Prince William.
According to the Daily Mail, Diana feared the gown was "so racy, in fact, [she] very nearly didn't wear the dress to New York's Met Gala for fear Prince William, then 14, wouldn't like it being so revealing."
But it wasn't just his mother's fashion choices that concerned the teenage Prince.
In fact, Prince William would complain to friends about how Princess Diana's public life "embarrassed" him, according to one royal biographer.
Despite Prince Charles and Diana's best efforts to protect their sons from the split, Prince William and Prince Harry were inevitably affected by their parent's divorce.
But according to biographer Katie Nicholl, the couple's elder son was particularly upset by the media attention his mother attracted during their high-profile divorce.
In her 2010 biography William and Harry, the royal author spoke to Prince William's childhood friend Kitty Dimbleby who was close to the Royal at the time.
She said: "I do remember William being distracted by what was going on at home.
"At the time there was a lot in the newspapers about Charles and Diana's marriage being in trouble."
She added: "William told me, 'Papa never embarrasses me but Mummy sometimes does.'"
Although Princess Diana and Prince Charles' divorce was finalised in 1996, the couple had separated three years before.
In an infamous 1995 Panorama interview, Princess Diana acknowledged rumours of Prince Charles' affair with Camilla Parker Bowles and said: "Well, there were three of us in this marriage, so it was a bit crowded."
But despite their messy divorce – which stripped Princess Diana of her title and office – the feuding couple did put on a united front for the sake of their children.
While Prince William was a student at Ludgrove boarding school, the biographer added: "Despite their feuding, Diana and Charles made an effort to visit William."
A former schoolmate told the biographer how Diana would spontaneously turn up to her son's school for visits.
"There was never a big deal when she showed up at the school and she seemed to like that," they recalled.
"For us boys she was just William and Harry's pretty mummy, not a princess."
In more Royal Family news, Princess Diana asked her boydguard "do you think they'll do that to me?" the day after Gianni Versace's murder.
And Princess Diana "hit Prince Charles over the head during his bedtime prayers", royal biographer claims.
Plus Princess Charlotte is the spitting image of a young Princess Diana in Cambridges' Christmas card, fans claim.
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