Princess Diana Once Wore A Different Outfit Just to Hide Her Bold Swimwear from Paparazzi

Princess Diana was known for captivating the masses, whether through bold fashion statements or her compassionate demeanor. Among her many iconic looks, one that continues to intrigue is the dress she wore to shield her choice of swimwear from the relentless paparazzi during a family vacation in 1990. Diana, often at odds with the media yet adept at managing her relationship with them, orchestrated a bikini switch.

During her vacation in the British Virgin Islands, Diana was photographed wearing a striking cheetah-print one-piece swimwear paired with a matching sarong. The outfit quickly became celebrated as one of her standout looks. Unbeknownst to many, this ensemble was a deliberate cover-up for a 'microscopic' red bikini underneath, as revealed by former royal correspondent, Jane Moore. As per Instyle, Moore, during an episode of I'm a Celebrity...Get Me Out of Here!, explained Diana’s strategy to control media coverage.

Moore said, "She would go on holiday, and all the media would go as well. Then her detectives would come over and say, ‘If you leave her alone all week, on Wednesday morning, she’ll come onto the beach, and you can take some photos." On the agreed day, Diana appeared on the beach in her cheetah-print swimsuit, accompanied by her young sons, Prince William and Prince Harry, who were snapped playing in the sand. Once the paparazzi's boat drifted far enough from the shore, Diana slipped into her daring red bikini, a move that sent photographers scrambling to capture the unexpected sight.

“Just when we’re so far away, she’s come back out onto the beach in the most microscopic red bikini that you’ve ever seen,” Moore recalled. The frenzy among photographers grew as they tried to persuade their boat operator to turn around. “All the photographers were throwing money at our boat guy, going, ‘Turn around!’” Moore added. Diana's calculated dealings with the media were not unusual. Moore emphasized that the Princess of Wales maintained a strategic relationship with the press, often making agreements to balance her need for privacy with the public's insatiable interest. “She played it very well,” Moore noted.

This incident was one of many when Diana wittingly outsmarted the media. Paparazzi photos of Diana were always highly sought after by news outlets, and she devised a strategy to diminish their value. Jenni Rivett, Diana’s former personal trainer, shared that the Princess intentionally wore the same sweatshirt to the gym, day in and day out. "Every single session, all the media camped outside with their cameras and lenses… I remember one of her strategies was that she was going to wear the same Virgin Active sweatshirt for every single session," Rivett told Hello! magazine.

Diana's ingenuity didn’t stop there. Whenever she stepped out of a car wearing a low-cut dress, she would hold a clutch in front of her chest, effectively shielding her cleavage from photographers eager to capture a scandalous shot. According to CheatSheet, designer Anya Hindmarch, who collaborated with the Princess, revealed that Diana humorously referred to these clutches as her 'cleavage bags.'