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For starters, she wore that dress during a completely different vacation.
Before realizing their marriage was over, Princess Diana and Prince Charles took one last “romantic” (those quotes are working overtime) trip to Italy as a second honeymoon. And as The Crown’s first episode of season 5 make all kinds of clear, the trip was tense. However, the episode takes more creative liberties than usual when it comes to Charles and Diana’s vacation, and the time has come for a quick fact check.
It was a private vacation, so it’s kinda unclear! In fact, the only information we do have is that Charles and Diana went to Italy in early August 1991. Since the trip was for family and friends only, there aren’t many photos, but—as Insider reports—Diana and Charles were pictured boarding a yacht on August 7, and Shutterstock (a photo distributor) describes the image as their “second Honeymoon:”

But again, since this was a private trip, we simply cannot know what was said on board. Meaning much of what happened during this episode of The Crown is pure speculation—including Charles and Diana’s argument, Charles deciding to head back early, and Charles arranging a meeting with Prime Minister John Major (which we now know never even took place).
On top of pretty much inventing everything that was said/done during their Italy trip (fair enough, the show is fiction), The Crown appears to have borrowed inspiration for Diana’s outfits from a different trip altogether. See this short-sleeved floral dress that Elizabeth Debicki wears in the show?
As Town & Country notes, it’s a recreation of this dress, which Princess Diana wore during her and Charles’s 1992 trip to Seville:
Meanwhile, we also see Diana in a recreation of the leopard print swimsuit + skirt that she wore during a trip to the British Virgin Islands in 1990:
But perhaps most significantly? Ahem:
Princess Diana and Prince Charles went on vacation to Italy in August 1991, which The Crown covers in episode 1. The show then depicts Diana making tapes for Andrew Morton’s book in episode 2. But in reality, the creation of these tapes happened months before.
According to Sara Bradford’s book, Diana, the Princess of Wales started recording tapes for Morton in May 1991. Charles and Diana then spent their 10-year wedding anniversary on July 29 dining at Highgrove and took their Italy trip in August.
Of course, The Crown does imply that the recording process took a while, so there’s definitely room for their timeline to be a little flexible. But still, the more ya know!

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