If Lady Di defined the British style of the 1990s, it's Carolyn Bessette Kennedy who did the same on the other side of the Atlantic.
Though both tragically died within just a couple of years of each other, their style legacy continues to stand strong by crossing borders and timelines to perfectly capture the nostalgia of their original era. And just as Diana's iconic looks returned to the spotlight thanks to Netflix's The Crown, her American counterpart is once again entering our collective consciousness, this time through Ryan Murphy's latest project.
The first edition of Murphy's new anthology series Love Story focuses on the complex relationship between Bessette (played by Sarah Pidgeon) and John F. Kennedy Jr. (played by Paul Anthony Kelly), as well as the media's turbulent coverage and harassment of the couple. Whether you like Ryan Murphy's sensationalist, high-stakes approach to storytelling or not, you simply can't deny the visual impact of Carolyn Bessette. Even in this remade, glossy version of events, her style holds up.
Armed with just Bessette's name, one quick scour through Pinterest results with a whole line-up of looks that seize the effortlessness we all yearn for. It's nineties fashion at its best: minimal but still full of personality and attitude. Although she definitely nails the formal look without looking like there's too much thought put into the process, it's her everyday looks that feel particularly timely for 2026. Thanks to the fit, wash and styling choices, images that feature Carolyn Bessette's jeans look like they were snapped by street style photographers during the most recent fashion week season in Paris or Milan. It's no wonder then that everyone seems to be coveting that mid-waist, bootcut jean right now.
After staring at photos of those outfits for slightly too long, you might start feeling like her essence has entered the building. But pulling off a Carolyn Bessette look is harder than you think. As evident in that catastrophic first look at the Ryan Murphy show that caused an online ruckus and even resulted in the showrunners hiring a new costume designer, finding the recipe to her style is a near-impossible task. So much of what we love about it is her attitude to simplicity and the way her gorgeous face frames these looks. Her beauty is undeniable and once-in-a-lifetime – and just wearing a similar dress wouldn't necessarily get you there.
So instead of trying to copy her looks and failing, we picked out six style lessons and accompanying key pieces that will help emulate her style today.
Cropped kick-flare blue jeans
Let's start with the secret ingredient – the exact pair of Carolyn Bessette's jeans that perfectly encapsulates her style iconography. A cropped, kick flare denim trouser in a shade of blue, with a mid-waist and a generous, worn-out fit. Sounds simple, but finding the exact style might feel like looking for Cinderella's slipper. The key, though, is in treating them as a go-to, wearing them with daily and embracing their patina. Levi's has a pretty exact match in their 725™ Kick Boot jean, as does Aligne, though you could also find an old pair of bootcut jeans and take them to your tailor for a crop.
The cropped kick-flare is a pretty universally flattering shape, so style them with block heel sandals or loafers for that nonchalant, everyday look, completed with a slim-fitting black top and a sleek up-do. It's the off-duty uniform that never goes out of style.
As someone who had worked in the fashion industry, Carolyn Bessette's access to clothes was expansive. Her close (but complex) relationship to Calvin Klein – another archetypal icon of the 1990s – was particularly evident in the clean lines of her outerwear. Today, finding a similar coat could prove quite difficult – single-breasted, knee-length, tailored without being too slim-fitting. In black, this type of coat is one you will probably keep hold of for the rest of your life. To make sure you maintain that Bessette vibe, pick pieces that have strong but not overpowering shoulders, and make sure to make use of the pockets. The more you wear it, the more real this piece will feel.
Soft square-toed boots
The quintessential 1990s shoe had its biggest fan in Carolyn Bessette. The unassuming elegance of a soft square-toed boot will forever be synonymous with this style icon. Worn as part of her work uniform as a fashion publicist as well as on the streets of New York in her role as political royalty – this shoe is a true code-switching staple. Because they were such a cross-generational piece during their original time, you will find numerous pre-loved pieces on Vinted and eBay, as well as in most of your local charity shops. But if you're looking to invest in a new pair, make sure to consider the balance of the toe box (sleek rather than chunky), the heel (wide rather than thin), and the shaft (close to the ankle).
Signature accessories in neutral colours
Just like with the rest of the wardrobe, Carolyn Bessette had a no-fuss approach when it came to accessories. Her favourite Prada bag was renamed after her back in 2023 – it's basically your most classic rectangular shoulder bag with minimal lines. But it's the headgear that gets referenced the most today, from street style to catwalks to red carpets. Zoe Kravitz is one of those new style icons who consistently bring out pieces that look like they came straight from Bessette's wardrobe. Her oval-shaped glasses from Selima Optique layer perfectly with a thick tortoise headband purchased from a pharmacy or a blue scarf worn as a bandana.
While method dressing and style transformations might seem tempting due to their makeover-y nature, Bessette's static approach to dressing feels quite contemporary and connected to the capsule wardrobe trends of today. Finding signature pieces that can be worn again and again is particularly helpful when searching for your own personal expression of style.
The act of not trying too hard can be quite difficult for some of us, especially when it comes to formal events. But take a leaf out of Carolyn Bessette's book and opt for pieces that feel totally timeless and almost ‘uneventful’. At first, you might be fearful of feeling underdressed – but that's the point! Instead of trying to make a bold statement in a fancy environment, taking the understated route offers a great alternative that instantly lowers the pressure.
A great example is Bessette's wedding dress – the most classic white silk slip, designed by Narciso Rodriguez, which was the total antithesis to the frills of the British royal wedding. Similarly, Bessette's use of a classic white Oxford shirt in formal environments should be studied – instead of buttoning it up, tuck it in a wrap shape to elevate this wardrobe staple.
There's a sort of urban legend that says Carolyn Bessette never wore colour. And yes, most of her iconic looks were in black, white or camel. However, she also had the ability to skilfully pull off colours most would find difficult to wear. A vivid blood orange coat in a patterned bouclé? The key is to downplay the rest of the look, including a soft bootcut jean and a woollen beanie. It's the contrast of classically masculine and feminine elements, made even better with the unintentional (but totally intentional) matching with her partner.
