The photograph may have been kept out of public view for decades, but its story is ultimately less about a secret picture and more about the extraordinary scrutiny surrounding Princess Diana.
In 1987, Diana was still one of the most photographed people in the world. Almost every detail of her public appearances—from the people standing beside her to the clothes she wore—could become the subject of headlines. A seemingly harmless photograph with David Bowie therefore carried a significance far beyond the moment itself.
According to Denis O’Regan’s account, the request not to publish the photograph came from the palace shortly after the concert. The concern was reportedly connected to Major James Hewitt, who had accompanied Diana that evening while their relationship remained largely out of public view. Hewitt deliberately avoided photographers, and O’Regan said he did not initially have reason to photograph him because his identity was not widely known.
Diana’s appearance that night also attracted attention. She had chosen leather trousers rather than the more traditional clothing expected of a member of the royal family. Diana later explained that she wanted to dress in a way that made sense for her age and for the audience around her. It was another example of how she was gradually developing a public style that sometimes differed from royal expectations.
The photograph with Bowie captured a very different side of her. Rather than the carefully staged royal portraits people were accustomed to seeing, it showed Diana relaxed and smiling beside one of Britain’s most famous musicians. Bowie, meanwhile, was at the height of his international fame, making the image a fascinating snapshot of two major cultural figures sharing an informal moment.
For O’Regan, however, the decision to keep the photograph unpublished was straightforward. He had received the palace’s request, understood the circumstances surrounding Diana’s evening, and chose not to release it. Decades later, he still regarded that decision as the appropriate one at the time.
Now the photograph can be viewed without the same immediate consequences it might once have carried. The people involved have long since moved beyond the events of 1987, and Diana’s relationship with Hewitt eventually became public.
What makes the image remarkable today is not simply that Diana was photographed with David Bowie. It is that a single photograph could once have been considered significant enough to keep from publication.
Seen nearly four decades later, the picture offers a small glimpse into an era when Princess Diana’s private life, public image, friendships, clothing, and even casual encounters could become matters of intense concern.
And perhaps that is what makes the long-hidden photograph so fascinating: it wasn’t a scandalous image—it was simply a moment of Diana being young, relaxed, and herself, captured beside a music legend before the world knew just how much was happening behind the scenes.