John F. Kennedy Jr. and Carolyn Bessette Kennedy have regained traction in the media through their unforgettable and passionate love story, now revisited in the FX Networks/Hulu series Love Story. Beyond the relationship itself, their personal style is what’s really catching viewers attention, influencing fashion lovers and bringing back some of the trends that once defined their era.
The Resurgence: Social Media & New York Street Style
Across social media, people have been recreating and taking inspiration from the couple’s style. Men are leaning into that preppy, effortless look, while women are drawn to Carolyn Bessette’s sleek minimal aesthetic. On TikTok, some users post carousel edits of the two walking through New York in effortlessly put-together outfits, while others create styling videos, recreating their looks with staple pieces like headbands, glasses, or flat caps. There’s a clear fascination with their relationship, but even more so with the idea of embodying a wardrobe that feels both elevated and attainable.
Looking back at the 1990s adds a strong sense of nostalgia to this trend. The decade continues to influence pop culture, fashion, and film, making it especially appealing to older Gen Z and younger Millennials. It also aligns with the ongoing “quiet luxury” movement – an effortless, understated style that feels polished without trying too hard, and one that people are increasingly drawn to.
Walking through the streets of New York, its noticeable that men have been sporting flat caps, a signature piece now associated with JFK Jr., especially following the release of the new series.
Carolyn Bessette Kennedy: Effortless Minimalism
Carolyn Bessette Kennedy’s style isn’t entirely new, but it’s become a major source of inspiration for women who desire to have that 90s chic look. Similar elements have appeared in early 2000s films and series like The Devil Wears Prada, Sex in the City, Cruel Intentions, Girlfriends with staples like headbands, black turtle necks, and silk midi skirts with strappy heels. These looks have evolved into modern trends like the “office siren” aesthetic, often tied to characters like Serena in The Devil Wears Prada, play by Gisele Bündchen.
CBK’s style offers easy wear, often centered around blue jeans paired with simple tops like a black long sleeve or a crisp white button-up. She kept her accessories minimal, usually opting for small oval frame sunglasses and a headband or head scarf. Its a look that feels effortless and accessible, built on pieces many women already have in their closets, while still offering a clear sense of direction when it comes to styling.
The “Carolyn Bessette Kennedy effect” is the term that has been circulating on social media. Her time at Calvin Klein adds another layer of appeal, especially for women interested in the fashion industry. Her look carries more weight because of her connection to fashion, but it’s really the timelessness that keeps people hooked. It never really feels out of place, aligning perfectly with the idea of a capsule wardrobe.
Users on social media also talk about the “rules” behind her style, especially when it comes to tailoring and fit. There was a clear attention to how her clothes sat on her body—everything was either perfectly fitted or proportioned in a way that felt intentional. The precision, combined with the minimal approach, is what makes the simplest outfits look elevated.
JFK Jr.: Preppy Meets Nonchalance
JFK Jr.’s style has also been catching on with men, especially across social media. Many are creating styling videos that lean into his preppy aesthetic with oversized blazers and trousers for a more polish, “politician” look, or flat caps paired with baggy jeans and vests for something a little more casual. His style also pulled elements of the time he was in, 90s urban culture, with pieces like Kangol hats reflecting trends popularized by figures like Denzel Washington and Spike Lee. At the same time, his preppy roots come through in his tailored suits, often favoring designers like Giorgio Armani.
Similar to Carolyn Bessette’s style, men are drawn to the timelessness of JFK Jr.’s look. There’s an appreciation for his nonchalant, effortless approach to dressing. Many have been recreating this by wearing simple, tailored suits and labeling it as “JFK Jr. style,” or by mixing pieces – like pairing a suit with backwards baseball caps as a nod to what he wore. What stands out to men was his ability to blend different styles rather than staying in one lane. JFK Jr. definitely drew inspiration from Black creatives in the ’90s who helped shape and define that style. Their influence played a key role in the foundation of the look he became known for.
The couple’s lasting impact on fashion today shows how quickly past eras can resurface and feel relevant again. Although they didn’t invent the minimalist, effortless style, their status and media exposure definitely helped popularize it. Through social media, their timeless aesthetic has found a new audience, proving that good style never really goes out of fashion.
