Stores
How JFK Jr.’s active lifestyle shaped one of the most effortless off-duty wardrobes of the 90s
With Ryan Murphy’s new FX series Love Story: John F. Kennedy Jr. and Carolyn Bessette, the couple is back in the cultural conversation. Most of the attention, understandably, is focused on Carolyn’s wardrobe. But for the fellas, JFK Jr.’s style is worth a closer look too.
Long before “athleisure” was a thing, he was casually mixing sport and tailoring — suits while riding his bike (often with a backpack), running shorts that actually saw a few miles, easy knits worn like everyday staples. As a naturally active guy with places to be, he dressed for the life he was living. Often that meant biking through Manhattan to get across town quickly — and to shake the paparazzi.
Yes, it helped that he was tall, handsome, and a Kennedy. But the real appeal of his style was the personal and the practical. He dressed like a real person who was dressed for the day ahead, while still allowing for the occasional eccentric touch: a beret here, hiking boots with a suit there, trousers rolled up mid-bike ride.
That slightly rumpled, sporty ease still holds up today — the kind of style that tends to look good on a man, and even better to the person standing next to him.
So, while the joy of his style is that he was truly adding his own personal spin on things, here are a few things worth stealing from the playbook.
The Windbreaker
JFK Jr. understood the value of a light jacket. Whether cycling through Manhattan or walking along the water, he often reached for something functional — a windbreaker, fleece, or easy sport jacket that could handle the elements without looking overly technical. It’s the same logic that makes these pieces useful today: light enough to throw on, tough enough for unpredictable weather, and casual enough to wear almost anywhere.
The Everyday Shorts and Sweats
You’ll find plenty of photos of him in suits, but just as many in shorts — rollerblading in the park, on a dock, or walking through the city like it was nothing. For JFK Jr., shorts and sweats weren’t just gym clothes; they were part of an everyday uniform. The key was relaxed proportions and simple styling — a sweatshirt, a tee, maybe a cap — with the occasional pop of colour.
The Backwards Cap
The backwards cap has spent plenty of time in “bro” territory, but somehow it worked on John F. Kennedy Jr. Maybe it’s because he wore it the way he approached everything else — casually, without trying to make a statement. The key is choosing the right cap: a classic adjustable style rather than a fitted, worn loose and natural. And after watching the first episode of Love Story, let’s just say: if there were a market for guys trying this look again this summer, it might be worth buying in early.
Cool Kicks
JFK Jr.’s sneaker rotation looked a lot like what you’d see at a good running shop today: Nike Air Max, Saucony, ASICS, New Balance. They weren’t precious lifestyle sneakers, just dependable trainers that could handle a run in Central Park, a bike ride downtown, or a quick coffee stop afterwards. That’s part of what makes the look feel so modern. A solid running shoe — comfortable, slightly technical, and worn without ceremony — still works just as well with shorts, sweats, or casual trousers.
The Gear to Stay in Motion
Part of what made his style feel so natural was that it reflected how he actually lived. He was constantly in motion — cycling through Manhattan, running in the park, sailing on weekends. The clothes followed the activity, not the other way around. That’s still the real lesson: the best sporty style starts with doing something. Whether it’s tennis, cycling, or getting outside on the weekend, the gear tends to look better when it’s being used.
