The name Carolyn Bessette-Kennedy is certainly a blast from the past, having been at the peak of her popularity just before she tragically died in a plane crash with her husband and sister over 25 years ago. She was known not only for being the wife of John F. Kennedy Jr., but also for her enigmatic nature and simple yet sophisticated style, which constantly caught the media’s eye.
So much unknown remained about Bessette-Kennedy when she sadly passed away, and it seems that it will forever remain that way. To this day, it’s still a rarity to find a full video that you can hear Bessette-Kennedy’s voice in, so much so that a Redditor put together a compilation of all the known clips of her speaking, and it turned out to be only a little over a minute long.
Perhaps it was her silence and mystique that kept the media wanting more of Bessette-Kennedy, and why she remained so highly photographed for various newspapers. After all, it wasn’t just JFK Jr. in the front photo that sold them; it was also the small glimpses of Carolyn and her chic looks.
Dubbed a “90s fashion icon” for her immaculate style — characterized by a muted color palette, minimalist accessories, and slicked-back hair (at least, some time after she began her relationship with JFK Jr.) — Bessette-Kennedy once perfectly defined what “timeless” really means.
However, I believe that an important question remains regarding that label: has social media’s recent discovery of Bessette-Kennedy negated the branding of her style as “timeless” by turning it into a trend, or has it instead strengthened it?
Since the release of the Hulu show Love Story: John F. Kennedy Jr. & Carolyn Bessette, all the buzz surrounding her fashion choices has come back stronger than ever. I first became aware of Bessette-Kennedy after stumbling across the book CBK: Carolyn Bessette Kennedy: A Life in Fashion while walking through a Barnes & Noble only a few years ago. However, I never could have guessed how strong a hold she would come to have on the internet.
Of course, Bessette-Kennedy has always been quite well known, and Sunita Kumar Nair’s book proves just that. But outside of the renewed exposure to her because of Love Story, what has made everyone decide that now is the time for Bessette-Kennedy to become the latest trend?
For someone who has been considered timeless for decades, it seems that many people are only just finding out about Bessette-Kennedy and the impact she had on 90s fashion. Ironically, it happens to be those very same people who are moving as quickly as possible to make an overpriced C.O. Bigelow tortoiseshell-patterned headband, something Bessette-Kennedy was known for wearing, an “investment piece.” But how long will it be before that headband is sitting abandoned in a drawer?
While taking inspiration from a celebrity for a new look is never a bad thing (I sometimes find myself influenced by trends, too), it’s not the same as it used to be. Before, the world used to have to turn to physical media like newspapers and magazines for street-style inspiration, whereas now, storefront links, “how-to” guides, mood boards, and starter packs are practically being shoved down our throats with every scroll.
The rush to buy whatever expensive pieces the latest trend calls for completely contradicts the timelessness of Bessette-Kennedy’s style. After all, what makes her outfits so special is that they can be recreated at any point, using pieces that can already be found in someone’s closet or purchased for a low price at a thrift store, which is a much better alternative to buying the same name-brand pieces she frequently adorned. Notably, some of Bessette-Kennedy’s most popular looks were as simple as it gets — featuring a plain-colored top, dark-wash jeans, and flat shoes.
Conversely, Bessette-Kennedy’s neutral looks are quite fashionable for being as simple as they are and easy to recreate, but I’m curious to know why these are the ones that everyone is obsessing over. From time to time, Bessette-Kennedy also styled bold, patterned, and colored pieces, which I believe to be a much stronger testament to how good her taste in fashion really was.
Could it be that no one is paying as much attention to Bessette-Kennedy’s more flashy looks because her plain and chic ones are all that have been seen in Love Story so far, or could it be because “timeless” is a more appealing label to the internet than “fast-fashion” is? More so, could this all go back to the fact that up until her death, Bessette-Kennedy was an extremely private person who shied away from paparazzi, interviews, and the media as a whole?
In a Marie Claire article about Bessette-Kennedy’s impact on fashion, it is said that Carole Radziwill, widow of JFK Jr.’s cousin Anthony Radziwill and a very close friend of Bessette-Kennedy, once explained that Bessette-Kennedy often resorted to wearing plain and muted clothing because she had hoped that if she wore enough outfits that looked alike, the paparazzi would eventually leave her alone.
Now, those same outfits are being plastered all over the internet with the assigned label: “the Carolyn Bessette-Kennedy effect.” For a generation that claims to crave authenticity, Gen Z has really struggled to escape the constantly shifting trend cycles and find its own timeless style.
Overconsumption and trend-hopping aside, I believe that Bessette-Kennedy’s fashion is truly something special. A quote that perfectly describes the allure and effortlessness of it comes from Alexan Ashcraft, founder of Trends of the Times, for a Yahoo Life article: “Carolyn wasn’t performing. Her clothes reflected her personal style and made sense for real life. In a fast-fashion, digital age where people are desperate to fit in and stay relevant, a style that embodies ease, timelessness, and confidence becomes irresistibly attractive.” However, with influencer culture and algorithm mentality brought into the picture, it’s hard to say whether Bessette-Kennedy’s style remains as timeless as it once was in the 90s.
There are certainly some similarities between Bessette-Kennedy’s looks and the current fashion of 2026, such as baggy jeans and flat shoes, that would point to the answer being yes. But when the internet finally decides to move on from Bessette-Kennedy’s style, which seems likely once all the episodes of Love Story are released and the internet has found something new to fixate on, then what happens? Does the label of Bessette-Kennedy’s style as “timeless” still stand—since, technically, it was revived—or does it become reduced to just another trend? I suppose that will have to remain to be seen.