The Carolyn Bessette Kennedy algorithm has my mind spinning with possible hidden messages. An obsession with the 90s is nothing new, but the viral Love Story: John F. Kennedy Jr. & Carolyn Bessette—and its interpretation of one of Calvin Klein’s most famous employees and her love life—has amplified interest in that specific era of the brand. The draw of minimalism’s finest hour has influenced a wide audience who now believe all they need to survive is a good pair of Levi’s, a minimal black top, a tortoise headband, and a cigarette. Maybe they’re not wrong.
Style has always been... personal. Getting dressed every morning is an art to some, a task on the list to others and a straight up miserable experience to (I hope) few. What leads up to that moment in people's closets is where it gets interesting. Buying decisions over the past decade have rapidly changed alongside technology and social media. In the age of influencers, whether you agree with it or not, we're largely prone to replicating what we've seen on our screens. Why is everyone wearing New Balance sneakers? Which color Stanley do you own? Did you all of a sudden need a pair of black, oval 90s-inspired sunglasses in February 2026? That's what Carolyn Bessette was known to wear.
Outrage over trying to emulate Carolyn (and John for that matter) made its rounds on news outlets and feeds because everything has to be a debate these days. How dare women try to copy her style, which was largely applauded alongside Carolyn's mysterious aura. How dare these women post their best CBK-inspired outfits for work because that's the exact type of attention she would have hated. How dare we borrow from something ending in tragedy.
Not sure which side I'm on. The whole ordeal brings up something deeper for me. It's really not about Carolyn or her impeccable taste. It might be a question of originality. Are we sitting front row to a personal style resurgence, or are we cosplaying a different era?
Another noteworthy trend circulating Instagram reels and posts lately goes something like this -- "bring back realness from the 90s". I've written a bit about 90s nostalgia and why I think we're edging back into a world craving reality, you can read that here. What I think people are reaching for, more specifically, is the individualism of style. Of a look. Of faces, aura, personality. The fact that Carolyn rarely wore make up to notice and dressed for herself, not the attention, may be part of the allure we're all feeling.
Now, arguably, we are in the age of individualism. More than ever before. When you have women like Odessa walking the red carpet alongside Jennifer Lawrence and Teyana Taylor, it's very obvious that expression of self is live and well. But to play devil's advocate, don't they also all seem to have a specific sheen to them? Don't the techniques in which they walk, present themselves, have polished hair & flawless makeup resemble each other? When people pull archived red carpet photos of Leo DeCaprio and Julia Roberts, they're struck by the realness that exudes from the screen. There's something raw there, like if you look close or long enough, you'll share each other's deepest secrets. A-listers are hardly relatable, but their social impact can't be denied and what they're wearing, how they're looking will always be a sign of the times.
Maybe more relatable are the fellow commoners filling our downtime between work tasks and helping us dissociate before bed. The ones we blame when yet another Amazon "dupe" shows up on the doorstep. (For the record, I've boycotted Amazon Fashion and have yet to have regrets. That's another rainy day discussion.)
No blame should land on any individual because blame isn't really what we're talking about here. A social observation would be a better term. And that observation is, even if people appear in a more "raw" form as they present their newest favorite find on stories, it's quite possible they are exactly why we all look the same while cheering on the sidelines at Saturday soccer matches. If modern personal style is simply copying who receives your likes on an algorithm, forget having an alluring CBK-esque mysterious aura.
All, and I mean, all of that to begin asking... what exactly is personal style anymore? Is it actually achievable in today's world? And if so, how do we find it?
Carolyn Bessette absolutely had it. Whether it came effortlessly or was deeply curated, I believe will be an infinite mystery. It does make me believe in personal style though. And I want this to be the beginning of a larger conversation—one where we try to answer questions like these. Stay tuned.