Princess Diana's "Cleavage Bags" Were the Chicest Royal Fashion Trick
Princess Diana's "Cleavage Bags" Were the Chicest Royal Fashion Trick
Katherine J IgoeThu, July 2, 2026 at 4:15 PM UTC
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Diana in her revenge dress with a black clutchCredit: GettyThe Gist -
Princess Diana was well-used to being photographed in the 1990s, and she had an ingenious trick to avoid revealing photos.
She would bring small "cleavage bags" to her public appearances, which she would strategically hold in front of her to prevent paparazzi from taking photos of her chest.
From her "revenge dress" to the gorgeous black Jacques Azagury she wore to her final birthday, these are the most famous instances of her cleavage bags.
After Princess Diana started the slow process to separate from Prince Charles in 1992 and later divorced him in 1996, she debuted a bolder, more fashion-forward, and exciting style. The change accompanied her newly short hair, which had debuted just a couple of years earlier in 1990.
During this period of grand transition, Diana wore outfits designed by modern designers Gianni Versace and Jacques Azagury, and also chose more dramatic gowns by her mainstay designer Catherine Walker than earlier iterations she'd worn. Her handbags had always been iconic, but she began favoring small satin bags during this time. It was a brilliant marriage of fashion and function: to prevent cameramen from getting a revealing or unflattering shot of her chest, she would hold them strategically in front of her. Her handbag designer, Anya Hindmarch, designed many of the custom pieces with her in secret, with tiny "D" details surreptitiously added to the bags.
The British handbag designer later shared in an interview with The Telegraph that it was a joyful process to make these practical-yet-stylish pieces: "We used to laugh when we designed what she called her 'cleavage bags,' little satin clutches which she would cover her cleavage with when she stepped out of cars." The royal's strategic posing became an iconic part of her public appearances, and it's one memorable example of Diana's long-lasting style ingenuity—instead of wearing higher-necked gowns, as she might have done earlier in her public life, she found a workaround. She helped humanize fashion for future royals, including Kate Middleton and Meghan Markle.
Below, the most famous instances of Diana's "cleavage" dresses, accompanying some of her most daring dresses.
01 of 07
At 'The Fugitive' Film Premiere, 1993
Diana wearing a navy dress and maching accessoriesCredit: Getty
Here, Diana attends the British premiere of The Fugitive in September 1993. One year after her separation, this would have been emblematic of her increasingly fitted outfits. It would define her newly chic style, especially for high-profile events; this one also saw movie stars Harrison Ford, Clint Eastwood, and Roger Moore attending. She paired a navy shift dress with tights and pumps and wore her sapphire and pearl choker as a statement accessory. Thus, the "cleavage bag," as we'd come to know them, functioned as a way for her to exit the vehicle, covering her chest.
02 of 07
The Iconic "Revenge Dress" With Matching Clutch
Diana's "revenge dress" included a matching black clutch
We most closely associate this event—a gala at the Serpentine Gallery in Hyde Park—with Diana's gorgeous and daring minidress. Designed by Christina Stambolian in black silk crepe, this "revenge dress" was the perfect outfit to "steal" headlines from Prince Charles; his documentary had premiered earlier in the day, wherein he'd admitted to cheating on Diana. She held the silk and velvet envelope clutch up by her chest, which was off-shoulder and surprisingly low for her. The ensemble became one of her most well-known dresses, but Diana still managed to retain a touch of modesty in even the most daring outfit.
03 of 07
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At the 'Haunted' Film Premiere, 1995
Diana wears a blue dress and black bagCredit: Getty
Diana, getting out of the car at the Haunted film premiere in London, performs her signature move. The blue evening dress was designed by Catherine Walker, according to Getty, and matched her tights and shoes to the look. The clutch looks to be black and offers a touch of contrast to the rest of the look. It's hard to see here, obviously, but the neckline was quite low relative to the princess' style. By this point, Diana was a pro at what the paparazzi might use to make a scandal, so the clutch preserved a touch of her privacy.
04 of 07
Attending a Dinner in Argentina, 1995
Diana in an all-red outfit, including bag and shoesCredit: Getty
Here, Diana held her small red bag slightly in front of her; from the profile, we can see how she protected her chest with her bag and, with her right hand, kept her hand at her dress hem. She was arriving for a dinner in Argentina during an official solo visit, and the lace gown was by one of her favorites—Catherine Walker. During this trip, Diana debuted several fashion-forward looks that were even more daring. Here, this was also a nice way to be visible to the crowd in such a bright color.
05 of 07
At a Performance of 'Swan Lake,' 1997
Diana matches her blue bag to her blue minidressCredit: Getty
In the last year of Diana's life, she really leaned in on her fashion instincts. This Jacques Azagury ice-blue minidress, for example, was one of the most avant-garde gowns of her life. It was beautifully form-fitting while still being relatively full-coverage and modest. And, per usual, she held her light blue satin clutch in front of her chest as an extra step of protection. The sweet blue matching sling-backs added a touch of formality—she was attending a performance of Swan Lake at the Royal Albert Hall, and had just been named Patron of the English National Ballet.
06 of 07
At The Tate Gallery On Her Birthday, 1997
Diana in a black sparkly dress and black accessoriesCredit: Getty
Princess Diana celebrated her last, 36th birthday at the Tate Gallery—which was holding a gala to celebrate its 100th birthday. The designer of her daring gown was, again, Jacques Azagury, in black Chantilly lace with sequins and beads. It was one of the "Famous Five" dresses he made for her in the last year of her life and called it his favorite. The small black clutch was a softer hue and a nice contrast, while still fitting into her all-black theme for the night. In hindsight, that color would take on a deeper poignancy.
07 of 07
At the 'In Love and War' Premiere, 1997
Diana in a navy dress clutches a black bagCredit: Getty
Here, Diana attended the In Love and War premiere in aid of the British Red Cross in 1997. As was often the case, this blue lace gown was designed by Catherine Walker. The thin clutch was an exact match to the color, and the gold accents perfectly matched her gold jewelry. By this point, Diana looked more confident and happy in her public events. She had established her new, post-divorce style—a nice mix of glamorous and daring. She wore what she wanted, and she wasn't about to give the paparazzi any salacious photos.
on InStyle
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