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 feature 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 have be replacing the other, there’s no denying the growing movement in fashion that adopted these same codes of Carolyn’s ‘90s minimalism and French girl style. Every New York influencer, stylist and editor I followed on Instagram claimed this same seeming irreverence to trends and committed to a timeless, neutral, capsule wardrobe of pillbox hats, frog clasp closures and silk scarf belts that ensured the appearance of effortlessness elegance at all times. The show began at the start of 2026, right after the peak of quiet luxury, and gave classic dressers a new lust for their pared-back sense of style as it wasn’t too dissimilar to the codes that it proceeded.
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 in with the same subject line around “Get the Carolyn Bessette look”. And understandably so! Carolyn’s uniform of knee length skirts, white shirts and t-shirts, Levi 501s and minimalist tailoring and dresses from Prada and the house that she worked for, Calvin Klein, was supremely elegant. Sarah Pidgeon, who played her in the show, continued this frenzy by also adopting her low-key, highly effective '90s style, even dying her hair a specific shade of blonde.
Carolyn’s uniform of knee length skirts, white shirts and t-shirts, Levi 501s and minimalist tailoring and dresses from Prada and the house that she worked for, Calvin Klein, 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, whilst they had the occasional whiff of quiet luxury and minimalism here and there, 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 were immediately hanging up their all-black hat, but there was a notable shift. One that made way for a more experimental, eclectic and colourful wardrobe. A wardrobe that one might expect from another very well dressed, highly referenced New Yorker born with the same initials; Carrie Bradshaw.
Whilst the spring/summer 2026 collections had the occasional whiff of quiet luxury and minimalism here and there, the general message was that maximalism was back on the menu. It paved a way for a more experimental, eclectic and colourful wardrobe. One that we might expect from another well-dressed New Yorker born with the same initials, Carrie Bradshaw.
Played and worn by Sarah Jessica Parker but put together by costume designer Patricia Field, Carrie’s style needs no introduction. A long-time champion of Manolo Blahnik shoes and the person that 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 to her ‘naked’ DKNY slip she wore on the bus, as well as the tulle skirt in the opening credits, she was an advocate for some of today’s most divisive comeback trends. 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 hardy tell. I’d estimate 90% of women dress with a similar identity to one of these two iconic New York women of the '90s. The Carrie Bradshaw’s (CB) of today are those diving into mermaidcore colour palettes, are likely having a Pucci summer and no doubt invested in one of the reedition designer handbags like the Saint Laurent Mombasa, the Gucci Indy, the Fendi Baguette or the Chloe Paddington. The Carolyn Bessette Kennedy (CBK) gang, however, are those that wear new styles from contemporary luxury brands like Toteme, Khaite and The Row. They’ll be wearing tailored skirt suits, tank tops with jeans and a thong wedge sandal and maybe a pair of Celine sunglasses and black headband for good measure.
Sure, there are a few overlaps in their style—some of Carrie’s most-loved outfits were surprisingly low-key (the white biased cut silk dress she sees Big outside his engagement party at The Plaza), it’s a fun exercise to compare the incomparable. It’s deeper than just minimalist vs maximalist, timeless vs trend. On the one hand, Carolyn had a uniform, on the other, if one tried to give Carrie a uniform to wear, she’d have it tailored into a mini skirt and place 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 by just these two women, that I’m forgetting many other well-dressed NYC celebrity inhabitants like Mary Kate and Ashley Olsen, Chloe Sevigny and Zoe Kravitz, to name a few—I know, but they weren’t born with the same ‘CB’ initials, so they don’t count.
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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.