Every so often a photograph surfaces that rewrites a small corner of pop culture history. This is one of them: Princess Diana and David Bowie, side by side, laughing together at a London charity concert in 1987. The image existed for decades without ever being published, and the reason it stayed hidden had nothing to do with Bowie at all.
A Night at Wembley That Almost Made History
The setting was a charity concert at Wembley Stadium, with Bowie headlining that evening. Diana, then 25 and already the most photographed woman on the planet, attended in support of the cause. The promoter Harvey Goldsmith arranged the photo opportunity, and Denis O'Regan, a photographer who had toured with Bowie and shot some of his most iconic images, was brought in to capture the moment.
According to O'Regan, retelling the story decades later, Diana herself wondered whether the rock star would agree to be photographed with her. Bowie, ever gracious, said yes. The picture was snapped, and it was everything a photo editor could want: natural, warm, two global icons sharing a genuine laugh.
Then the phone rang the next morning. The palace asked that the photograph not be published.
The Real Reason the Palace Intervened
The request had nothing to do with the image being inappropriate, and nothing to do with Bowie's presence. It was about who else was with Diana that night. The princess had arrived at the concert accompanied by Major James Hewitt, at a time when rumors about an affair between the two were swirling through London society and, in due course, were confirmed.
Hewitt had spent the evening deliberately avoiding cameras, and the palace was determined not to fuel speculation by letting any published image connect Diana's public appearance to the evening's private guest list. A cheerful photo with Bowie might have seemed harmless, but in the tabloid ecosystem of the late 1980s, any new Diana image from that night would have been mined for background clues: who stood where, who looked at whom, who was cropped out of frame.
O'Regan made the decision to hold the photograph, a choice he says he still supports. The negative sat quietly in his archive while the world moved on through the 1990s, through the divorce, through 1997, and through every retrospective since. He has said in interviews that respect for the palace's request and for Diana herself made the decision easy at the time, even though he knew he was sitting on one of the most desirable royal images ever captured.
The Leather Pants Nobody Forgot
One detail from that night did escape into the record. In her biography, Diana recounted the criticism she received for her outfit: leather pants, which pushed firmly against the boundaries of what palace advisers considered appropriate for a future queen. The garments reportedly did not sit well with the royal family at all, and the episode became an early example of the public's endless fascination with what Diana wore and what it supposedly signified.
Seen today, the fuss feels almost quaint, another reminder of how tightly the institution policed even the most harmless expressions of personal style during her years inside it.
Why the Photo Matters Now
The photograph's eventual emergence says as much about us as it does about 1987. Diana remains a subject of bottomless public interest, and every newly surfaced image triggers a fresh wave of reflection on her life and the way the establishment managed her. This one captures a rare intersection of worlds: the most famous princess in history and the most influential rock chameleon of his era, both at their peak, both famously guarded in public, both allowing themselves a moment of unguarded fun.
It also documents the machinery of royal image control at work. A single phone call prevented a picture from existing in the public record for decades, a small but vivid illustration of how palace preference once shaped what audiences were allowed to see.
A Portrait With Everything Except the Scandal
O'Regan's image finally gives people the chance to see what the palace preferred they never did: Diana enjoying herself, completely at ease, in the company of a legend. The irony is that the photograph itself contains no hint of scandal. It is simply two charismatic people laughing, with the messy human story of that year deliberately framed out of the shot.
Decades on, the picture feels less like an embarrassment and more like a gift, a window into an evening when music, charity and celebrity briefly shared a stage at Wembley. It documents a version of Diana that the official record rarely permitted: relaxed, modern, and completely at ease in the company of a music legend. The detail that kept it hidden, Hewitt's careful invisibility, is precisely the detail that makes its survival so remarkable.
The account above is based on the photographer's recollections and published interviews.
