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| NYC, USA 01/24/97 (644237) John John KENNEDY and his wife Carolyn with their dog. Photo © Evan Agostini/Getty Images |
With the debut of Ryan Murphy’s FX series American Love Story, the couple’s preternatural swagger has been thrust back into the limelight, introducing a fresh generation to their magnetic presence. I’ll admit, I was hooked; I devoured all six episodes in one sitting and I’m already counting down the days for the next instalment.
Why all the fuss?
The answer is simple. He was a pioneer of "personal style" long before the term was diluted into meaningless internet jargon. What he wore is worth getting right because it was authentic.
While researching their story, I found myself spiralling down a Google rabbit hole, questioning if such immense charm could actually be real. Interestingly, I realised I was looking at their clothes more than their history. Their wardrobes didn't just cover them; they revealed their characters.
While we are here to talk about JFK Jr., it’s impossible to mention him without Carolyn. They were, and remain, a visual 'unit'. A close friend of Carolyn’s once remarked that while she was notoriously private and camera-shy, her clothing was the only area where she felt comfortable revealing her true self. That hits the nail on the head.
The American Prince
Beyond the handsome face, the "American Prince" title, and the scandal-laden legacy of the Kennedy dynasty, John-John’s style was immortalised by its sheer nonchalance. You’ll never find a shouting logo or a garish display of wealth on him—and Carolyn was exactly the same. The image I’ve chosen as the header for this post - walking their dog in NYC - is my absolute favourite and the style that stays with me the most. It perfectly encapsulates their shared aesthetic. I am also equally obsessed with how JFK Jr. effortlessly paired a sharp suit with trainers and his signature backwards baseball cap. It was a masterclass in how to dress things down with confidence.
Even more legendary than his tuxedos were his casual New York moments - cycling through the city in jersey shorts, a basic white tee, and that signature reversed cap. He even made the bum bag look sophisticated.
That backwards cap is a crucial detail. It’s the quintessential 'American Boy' look, but with a refined edge. Not a rebel without a cause, but an 'It-Boy' with magnetic charisma. As a son of a political dynasty, his wardrobe was anything but mundane.
Whether it was the unexpected headband, the bandaged wrist styled like a pseudo-accessory, or a wool gilet layered over a patterned shirt, the details were fascinating. The beauty is that most of these elements are remarkably easy to find today. He mastered the art of taking 'business casual' staples and layering them until they felt like a high-end version of off-duty dressing.
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| Photos: Lawrence Schwartzwald |
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| John F Kennedy Jr (pictured here with wife Carolyn Bessette Kennedy) often wore a backwards baseball cap and sunglasses Credit: Shutterstock Editorial |
So, how do we mirror this timeless look today? Let’s break down the secret formula step-by-step:
1. The Outerwear is the Anchor
For both Carolyn and John, the coat was never an afterthought; it was the statement. Forget technical puffers; think timeless staples. A perfectly tailored topcoat, a suede bomber, or a rugged field jacket. The outer layer must be sharp enough to elevate everything underneath.
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| NYC, USA 01/24/97 (644237) John John KENNEDY and his wife Carolyn with their dog. Photo © Evan Agostini/Getty Images |
2. The Jeans-and-Sweater Formula
John-John knew how to strip back the layers. Stick to the basics: straight-leg denim, a crisp white crewneck tee, and perhaps a navy cardigan or a slim-fit cashmere jumper. No distressing, no oversized silhouettes, and absolutely no logos splashed across the chest. The vibe is fresh, athletic, and ready for movement.
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| Photos collected from Pinterest and Instagram |
3. The Gilet Masterclass
His use of vests and gilets was a stroke of genius. It was his "office-ready without the tie" solution—a formula that allowed him to transition from a boardroom to the pavement without skipping a beat.
4. The 'Personal' Accessory
He had a knack for humanising "business casual" with unexpected accessories. Whether it was a beanie or a chunky scarf that looked hand-knitted by a favourite aunt, he added texture and warmth to structured tailoring.
5. Make it Uniquely Yours
Regardless of his destination or the company he kept, John-John wore exactly what he felt like wearing. This is the truest definition of personal style. Even if you’re commuting by Tube rather than a private jet, don’t be afraid to add a bit of 'freak' to your 9-to-5 tailoring.
6. The Quest for the Perfect Suit
Every man should nail the perfect suit at least once. JFK Jr. favoured the double-breasted navy suit, often paired with a patterned red tie and classic black dress shoes. The crisp white pocket square was the final flourish that tied the entire ensemble together beautifully.
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JFK Jr.’s style was singular, timeless, and frankly, ahead of its time. The best part? He wasn't trying to be "fashion-forward." He was just a cool, high-profile man wearing clothes he genuinely liked, in a way that only he could.