3 min readComparisons between Diana, Princess of Wales and Carolyn Bessette Kennedy are easy to make. The pair were born just four years apart; each thrust into the media’s unrelenting gaze because of the men they married. In the ’90s, both were extreme paparazzi fodder with their every move photographed and commented upon.
Then, of course, there are the tragic deaths that further align them. Diana died in a car accident in 1997, while Bessette Kennedy was killed in a plane crash in 1999. Both were in their 30s. It’s unknown whether the two ever met, but they sat just a pew apart at Gianni Versace’s funeral.
Carolyn Bessette Kennedy at Versace’s funeral.
Diana, Princess of Wales at Versace’s funeral.
Since their passing, both women have transcended as style icons. While their wardrobes were admired during their lifetimes, what has since followed is such a fanatic celebration of what they wore that it has elevated them to idol status. In the case of Diana, it’s her off-duty wardrobe that has become most fixed upon, be it her gym sweatshirts or high-waisted denim—but not forgetting the revenge dress, either. Bessette Kennedy’s sleek, minimalist approach, meanwhile, quickly became the blueprint for the quiet luxury trend that dominated the 2020s. Her wedding dress is no doubt amongst Pinterest’s most-saved reference images.
What has proved most precedent in seeing both of these women become such muses, 30 years after their passings, is the television shows that have turned their very real lives into plotlines. In Love Story: John F. Kennedy Jr. & Carolyn Bessette, the story of how Bessette Kennedy met and went on to marry John F. Kennedy Jr. plays out, while the later seasons of The Crown charted Lady Diana’s arrival into the Windsor family and her subsequent struggle to leave it.
Elizabeth Debicki as Diana, Princess of Wales in The Crown.
Sarah Pidgeon as Carolyn Bessette in Love Story.
Both have given a new generation of imitators and admirers a look not only at the truly fascinating lives of these women but also at how they dressed for those exceptional lives. Many of the costumes have remained close to the source material, recreating real outfits to the nth degree, while others riff on the hallmarks of their wardrobes. Think of Diana’s move from preppy teenage knits to natty Versace dresses and Bessette Kennedy’s excellent selection of muted outerwear.
The badge of “style icon” is too often freely assigned in 2026, but these women, whether they would care for it or not, simply are exactly that. Despite being a moniker linked to fashion choices, a style icon doesn’t always come down to having a wardrobe full of the best clothes. It comes down to personal style, and these two had it in abundance.
It is as simple as this: Both Diana and Bessette Kennedy understood what worked for them—be it as an extension of their personalities or for the messages they were choosing to say through their sartorial choices—and they rarely veered from this. Sure, there were moments of trend-tapping, especially in the case of fashion industry insider Bessette Kennedy, who pulled from the runway collections of Calvin Klein, Prada, and Comme des Garçons to shape her enviable wardrobe. But decades on, their fashion approaches are aligned in their consistency and consideration.
If you look at the pieces they wore in the ’90s, there’s an almost formulaic approach to their outfits with repeating patterns appearing time and time again. Their silhouettes rarely differ, and color palettes tend to also remain within a select set of shades.
It’s a lesson for all of us to observe and apply. In today’s overwhelming trend cycle, where social media dictates the quickening frequency of what’s in and what’s out, it can be easy to get lost in the noise. Sticking to some core personal style principles of your own will not only allow you to silence the overconsumption that comes with trend cycles, but will also help you discover more about who you are and what that looks like.
We can’t promise you style icon status like we have afforded Diana and Bessette Kennedy, but we can be sure you’ll look and feel better by taking on their considered, curated approach.