Carolyn Bessette Kennedy vs. Carrie Bradshaw: Which Iconic New Yorker Is More Your Summer Style?
Carrie Bradshaw and Carolyn Bessette Kennedy are two of the best-dressed New Yorkers of all time, yet they have very different styles. Here, editor Rebecca Rhys-Evans investigates how these two '90s New York icons have impacted the way we dress today.
A few months ago, I wrote an article questioning whether New Yorkers were the "new" French girls. In the story, I claimed that the huge interest in '90s minimalism spawned from Love Story, the hit TV show that depicted the late Carolyn Bessette Kennedy and her husband John F Kennedy Jnr, had inspired an aesthetic amongst fashion insiders in the city that wasn’t too dissimilar from that which we often associate with French women.
Whether or not you agree that one might be replacing the other, there’s no denying the growing movement in fashion that has adopted these same codes of Carolyn’s ‘90s minimalism and French-girl style. Every New York influencer, stylist and editor I follow on Instagram claims the same seeming irreverence to trends and commitment to a timeless, neutral capsule wardrobe of pillbox hats, frog-clasp closures and silk scarf belts that ensure the appearance of effortless elegance at all times. The show began at the start of 2026, right after the peak of quiet luxury, and gave classic dressers a renewed passion for their pared-back sense of style.
Countless publications, Substack writers and online commentators documented the meteoric chokehold "CBK style" had on womenswear earlier this year. Every high-street edit and marketing email came with a subject line around getting the look, and understandably so! Bessette-Kennedy’s uniform of knee-length skirts, white shirts, Levi 501s, minimalist tailoring and dresses from Prada and Calvin Klein (she worked for the brand) was supremely elegant. Sarah Pidgeon, who played her in the show, added fuel to the fire by adopting CBK's low-key, highly effective '90s style off-screen, even dying her hair the same specific shade of blonde.
Bessette-Kennedy’s uniform of knee-length skirts, white shirts, Levi 501s, minimalist tailoring and dresses from Prada and Calvin Klein (she worked for the brand) was supremely elegant.
But as the show ended just in time for spring, the new highly anticipated spring/summer 2026 designer collections dropped. These collections had an occasional whiff of quiet luxury and minimalism here and there, but on the whole they painted a different picture. Texture at Bottega Veneta! Ruffles and tulle at Dior! And sequins, florals, feathers and much, much more at Chanel! Finally, maximalism was back on the menu. And it’s not that minimalists are immediately hanging up their all-black looks, but there has been a notable shift, one that made way for more experimental, eclectic and colourful wardrobes; a wardrobe that one might associate with another very well-dressed, highly referenced New Yorker born with the same initials: Carrie Bradshaw.
The spring/summer 2026 collections painted a different picture, one that made way for more experimental, eclectic and colourful wardrobes; a wardrobe that one might associate with another very well-dressed, highly referenced New Yorker born with the same initials: Carrie Bradshaw.
Worn by Sarah Jessica Parker but devised by costume designer Patricia Field, Carrie’s style needs no introduction. A longtime champion of Manolo Blahnik shoes and the person who made the Fendi Baguette the first-ever It bag, with each episode of Sex and the City, fans knew to expect the unexpected from her outfits. From the Galliano for Dior newspaper dress and the "naked" DKNY slip she's wearing on the side of the bus to the tulle skirt in the opening credits, she was an advocate for some of today’s most divisive comeback trends, including capri pants (even those in camo print), crop tops, bandanas, boob tubes and exposed bras (always with the exposed bra!). Carrie did it all, whilst almost always in heels and always looking—as she’d say—fabulous.
Today, we might be in the midst of summer 2026, but look around on the streets or in your office, and you could hardly tell. I’d estimate 90% of women dress similarly to one of these two iconic New York women of the '90s. The Carrie Bradshaws (CB) of today are those diving into mermaidcore colour palettes, likely having a "Pucci summer" and no doubt invested in one of the latest re-edition designer handbags like the Saint Laurent Mombasa, the Gucci Indy, the Fendi Baguette or the Chloé Paddington. The Carolyn Bessette Kennedy (CBK) gang, however, wear new styles from contemporary luxury brands like Toteme, Khaite and The Row. They’ll be in tailored skirt suits, tank tops with jeans and a thong wedge sandal, and maybe a pair of Celine sunglasses with a black headband for good measure.
Sure, there are some overlaps in their style; some of Carrie’s most-loved outfits were surprisingly low-key (the white bias-cut silk dress when she sees Big outside his engagement party at The Plaza), but those are few and far between. It’s deeper than just minimalist vs. maximalist, timeless vs. trending. Carolyn had a uniform, but if one tried to give the same to Carrie, she’d have it tailored into a miniskirt and put a Tory Burch brooch on it. Where Carrie was appealing because she tried (who else wears heels with athletic shorts for a dog walk?), Carolyn was appealing because she didn’t. Effortlessness was essential to her aloof sense of cool.
Where Carrie was appealing because she tried (who else wears heels with athletic shorts for a dog walk?), Carolyn was appealing because she didn’t.
And before you tell me that New York style can’t be categorised just by these two women, that I’m forgetting many other well-dressed NYC celebrity inhabitants like Mary-Kate and Ashley Olsen, Chloë Sevigny and Zoë Kravitz, to name a few, I know, but they weren’t born with the same initials, so they don’t count here.
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Rebecca Rhys-Evans is a London-based fashion and beauty editor with a decade of editorial experience. She started working at Who What Wear UK in the summer of 2022, where she was hired to lead all branded content for the UK site. Be it styling the latest designer collections, or reviewing the most recent beauty skincare products, Rebecca is the voice (and often face) for Who What Wear UK’s commercial partnerships. A self-confessed internet obsessive, she loves all facets of content creation—be it writing, filming, art directing or styling—and revels in collaborating with brands to help harness their product and tell their story. Before Who What Wear, Rebecca contributed to FLANNELS.com, BURO., Polyester, Screenshot, Marie Claire, Refinery29 and Culture Trip, reporting on everything from internet culture, sustainability and trends.