With ‘Love Story’ wrapped up, fascination with John F. Kennedy Jr. and Carolyn Bessette-Kennedy has only intensified – and while opinions remain divided over how faithfully the series portrayed their actual relationship, one thing everyone agrees on is that it absolutely nailed their enduring style.
Decades later, the couple’s fashion still feels remarkably modern yet unmistakably ’90s: rooted in quiet luxury and marked by a mix of polish and nonchalance. It’s no surprise that the renewed attention around this tragic love story has coincided with an uptick in sales for CBK staples and a wave of urbanites describing their style as ‘JFK Jr-core.’ Here’s how you can bring a little of that JFK Jr. and Carolyn magic into your own wardrobe.
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The Crisp White Shirt
If there’s a staple item that perfectly captures both JFK Jr. and Carolyn Bessette-Kennedy’s understated sharpness, it’s the classic white shirt. Endlessly versatile, it could be worn tucked into a skirt for formal events or thrown over jeans and sneakers on a New York afternoon. Aside from his dressier shirting, JFK Jr. often gravitated toward relaxed cotton styles with rolled sleeves, while Carolyn leaned toward tailored fits that draped just right. The best part? You can tap into either look at any price point – from a perfectly cut Uniqlo Oxford or COS number to The Row’s luxe poplins or Armani’s classics. Buttoned up or worn loose, the crisp white shirt remains one of the simplest ways to mirror the couple’s shared sense of timeless, low-key elegance.
Classic Denim
No one did blue jeans quite like Carolyn Bessette-Kennedy – her love for the perfect bootcut pair is the stuff of legend. For diehard CBK devotees, the holy grail remains the Levi’s 517, a subtly flared cut that she wore with heels, sneakers, and everything in between. Before she became a style icon photographed on every Manhattan sidewalk, Carolyn worked at Calvin Klein and was naturally often spotted in the label’s instantly recognisable denim. Look to Levi’s for the classic Carolyn fit, or to labels like AGOLDE and Acne Studios for a more elevated take on minimal, all-American cool.
The Backwards Hat
Few accessories feel quite as tied to JFK Jr. as the backwards hat – a small but recognisable move that instantly gave his preppy style a more relaxed feel. In nearly every candid photo, you’ll spot it in some form: a ball cap or soft Kangol hat, flipped around and worn with the kind of naturalness only ‘America’s Prince’ could pull off. It was a recurring part of his off-duty uniform, pairing just as easily with gym clothes as it did with trousers and a button-down. To get the look, skip obvious logos and stick to neutrals – a navy Ralph Lauren cap, a faded Yankees classic, or a Kangol. It’s casual dressing at its best: low-key and entirely John-John.
Oval Sunglasses
Minimal and unmistakable, Carolyn Bessette-Kennedy’s oval sunglasses became one of the most lasting elements of her wardrobe. Her preferred pair came from Selima Optique, the New York brand behind her now-legendary Aldo frames, still available today alongside reissues aptly named the ‘Carolyn’ and ‘CBK.’ Worn with everything from a black slip dress to an oversized coat, those small rounded lenses became part of her mythology. You can find similar oval silhouettes everywhere now – from Gentle Monster and Ray-Ban to Celine and Maison Margiela – making it easier than ever to bring a little CBK into any outfit.
Tailored Coats
As perennial New Yorkers, JFK Jr. and Carolyn Bessette-Kennedy understood that winter style depends as much on structure as insulation. Their outerwear was always immaculate – Carolyn’s famous Prada camel coat quickly became a fashion reference point, while JFK Jr. gravitated toward dark wool overcoats worn with sweaters or suiting underneath. A long wool coat, a streamlined trench, or even your current favourite reworked by a trusted tailor can all get you there: few things convey the composed, city-smart cool of New York’s most stylish couple faster than a perfectly fitted coat.
The Silk Tie
While JFK Jr.’s flawlessly tailored suits are now the stuff of menswear legend, one of his more understated signatures was the silk tie – always knotted just so, adding an extra note of refinement. Even without a full blazer-and-slacks ensemble, you can borrow the same charm with a silk tie tied in a snug four-in-hand knot, instantly lifting a sharp shirt or casual jacket. Look to classic labels like Ralph Lauren, Brooks Brothers, or J.Crew for modern silk options, or scour vintage rails and eBay listings to hunt down true ’90s pieces for that lived-in texture and retro sheen.
The Pencil Skirt
Capture Carolyn Bessette-Kennedy’s mix of restraint and sensuality with the pencil skirt. Her looks were always pared-back, yet somehow more memorable than any louder trend. One of her most memorable moments? A camel pencil skirt paired simply with brown boots and a black top – a look that came to embody her poise. To bring that mood into the present, opt for a pencil skirt in neutral tones like beige, black, or navy, or switch things up with a soft pastel or rich chocolate brown for a more modern finish. Simple never looked so compelling.
The Tank
The Cartier Tank, one of the most elegant watches ever made, is a piece forever tied to both the Kennedy name and Carolyn Bessette-Kennedy’s pared-back sensibility. Carolyn’s Tank Louis Cartier – slim, gold, and understated — became as much a part of her look as her ponytail or oval sunglasses. The connection ran deeper than aesthetic: JFK and Jacqueline Kennedy Onassis famously wore Cartier, and JFK Jr. followed suit, alternating between his trusty Timex and his own elegant Tank Louis Cartier. While a genuine Cartier Tank Louis Cartier remains one of the ultimate quiet-luxury investments, there are also numerous brands that offer their own tank silhouettes at more affordable prices.
Editor’s Note: All listed prices were correct at the time of publication.
Born in Korea and raised in Hong Kong, Min Ji has combined her degree in anthropology and creative writing with her passion for going on unsolicited tangents as an editor at Friday Club. In between watching an endless amount of movies, she enjoys trying new cocktails and pastas while occasionally snapping a few pictures.
