I remember I first heard about Carolyn Bessette-Kennedy through my mom, who had lived in New York throughout the ’80s and ’90s. She spoke about her with a mixture of envy and awe.
Envy, because she was with America’s storybook prince, John F. Kennedy Jr., a monolith of a man with chiseled features that brought to mind Michelangelo’s “David.” Awe because of her simple but showstopping style, often highlighting the fact that she never wore any jewelry, sticking faithfully to neutral palettes and starkly clean silhouettes.
In 2026, Bessette-Kennedy’s look is back in full force, her legacy retold in the new biographical romance TV anthology “Love Story” (now streaming in the Philippines on Disney+).
In 2026, Bessette-Kennedy’s look is back in full force, her legacy retold in the new biographical romance TV anthology “Love Story”
Its first season covers JFK Jr. and Bessette, staying close to the public whirlwind—much of it captured, perhaps a little unfairly, by the press, from fights in Central Park to their ultra-private wedding, and eventual untimely death in a plane crash. The show also imagines more intimate moments between the couple and the people around them, including Jackie Kennedy-Onassis, played by Naomi Watts, Sarah Pidgeon taking on the role of Carolyn, and newcomer Paul Kelly as JFK Jr.
While there have been reels of young men in New York emulating JFK Jr.’s style with backwards pageboy caps and ’90s sports jackets, often on bicycles or rollerblades, it’s Bessette-Kennedy, who once worked and rose through the ranks at Calvin Klein, who is rising in relevance for young women’s fashion.
And maybe that’s because her uniform of tailored staples is all the more attractive now. In a time with rising oil prices and cost of living, her way of dressing proposes the much-needed discipline to refuse the chase for fleeting trends, as well as the resistance to check out that online cart again.
Here are some of the elements that made Bessette-Kennedy iconic in her style—which we can easily emulate today, helping us dress better, with much less, and in a wardrobe that lasts.
No jewelry, but maximum impact
Perhaps one of the bravest and most distinctive style choices of Bessette-Kennedy was that she stripped things back in terms of accessories.
She often stepped out with just a red lip and fresh manicure, without an earring, necklace, or bracelet in sight. Instead, her outfits focused on the line of a bespoke coat or the perfect cut of a slip dress. Through this jewelry-free look, attention was drawn to her features, stark as they already were, highlighting her porcelain skin, high cheeks, and flaxen blonde hair.
A safe, neutral closet
Perhaps influenced by her time working as a publicist at Calvin Klein, which is known for its sleek aesthetic that still managed to be sensual, Bessette-Kennedy’s wardrobe did the same. Her sense of style rejected visible designer logos, very much aligned with today’s “quiet luxury” style.
Her favorite brands often included high-quality designers such as Prada, Yohji Yamamoto, and Versace, where she opted for simple bootcut jeans, camel-colored coats, turtlenecks, or simple strappy sandals.
Wardrobe staples that last
While the spectrum of colors rotating in her closet often stuck to neutrals, such as black, ivory, camel, and navy, these were always elevated.
Some of the identified neutrals she’s worn include designer-invisible labels, such as a black Ralph Lauren turtleneck paired with brown Helmut Lang pants, Levi’s 517s jeans, crisp, button-up white shirts, loafers, and black shoulder bags, all of which reject attention.
This rejection of attention reflected her own attitude toward the media—you’d be hard pressed to find a video of her speaking online. But just like her personal bearing, each fashion choice held its own.
This rejection of attention reflected her own attitude toward the media—you’d be hard pressed to find a video of her speaking online
Simple signature accessories
Bessette-Kennedy’s accessories were as minimal and purposeful as the rest of her wardrobe. Today, with the accessibility of sunglasses, you likely have more than one pair in your drawer. Besette-Kennedy was known to regularly wear the same oval Aldo shades from Selima Optique. Later, posthumously, the brand named a pair “Carolyn” in her honor.
Occasionally, she also carried a black Birkin bag as part of her uniform. And while we can’t all afford a Birkin, she was known to regularly wear a drugstore headband. Bessette-Kennedy often donned a practical, elegant tortoiseshell headband to lock in her wispy hair. Some speculate she got the Charles J. Wahba headband from Greenwich Village apothecary C.O. Bigelow, others from Upper East Side pharmacy Zitomer.
Quality over quantity, always
Through Besette-Kennedy, we could be inspired to collect fewer pieces that are better made, with fabrics that hold and cuts that last.
Her distinctive, sleek ’90s style resonates very much today. And it wasn’t just because she was a gorgeous blonde but also because her minimalism was easy, and her chosen silhouettes don’t date.
Now, with oil prices rising and the looming threat of a recession, Besette-Kennedy’s disciplined, oft-repeated outfits and style of restraint could just be the inspiration we’re looking for—not in a sense of buying more clothes to match her style, but to look at the own quality pieces we have existing in our wardrobe.
And maybe even resist that “add to cart” urge for fleeting trends.
