There’s a particular kind of envy that comes with watching old footage of JFK Jr. The man made looking effortless look easy, which is maybe the cruelest form of style gatekeeping. You can’t buy his cheekbones. You can’t inherit Camelot. But thanks to the FX series “Love Story,” a whole new generation is wondering if they can at least borrow his closet.
The thing about JFK Jr.’s style wasn’t that it was complicated or expensive or even particularly trendy. It was the opposite. He wore clothes like he had somewhere better to be, and somehow that made everything look better.
The Anti-Fashion Philosophy
What made JFK Jr. actually different from every other political scion is that his style didn’t scream “I’m trying.” It whispered it. Chelsea Volpe, a fashion stylist who’s spent time thinking about this, nails it: “He mastered that elusive balance of American polish and downtown ease.” The guy understood proportion instinctively. Broader shoulders. Trim trousers. Nothing fussy. Nothing that demanded attention.
This is where most people get it wrong. They think JFK Jr.’s look was about collecting pieces. It wasn’t. It was about editing ruthlessly. He wore restraint like armor.
“There was no over-accessorizing, no trend-chasing,” Volpe explained. “Just great basics, great fit, and great posture.” And honestly, the posture part might be the cheapest upgrade you can make to your entire wardrobe.
Start with Soft Tailoring
If you’re going to do this, you need to understand that JFK Jr. wore tailoring that moved with him. Not stiff, not structured, just natural. Soft shoulders. Lightweight fabrics. Menswear that actually breathes.
A navy blazer. A charcoal suit. Maybe a knit tie instead of silk. These are your starter pieces. The key word here is ease. If your clothes feel like they’re wearing you, you’ve already lost.
The good news is you don’t need to drop thousands at Armani, which is what he actually wore. Vintage is your friend. Check eBay, Depop, Poshmark, your local thrift store. Search for “Vintage Mens Ralph Lauren” or “90s LL Bean” and you’ll find actual pieces from that era. They’re cheaper, they’re better quality than most new stuff, and honestly, there’s something more authentic about wearing clothes that lived through the 90s instead of just imitating them.
The Denim That Matters
JFK Jr. didn’t do distressed. He didn’t do skinny. He wore classic, dark rinse jeans, mid-rise, straight-leg, structured. That’s it.
“Dark rinse denim instantly looks intentional and grown,” Volpe said. And she’s right. There’s something about dark denim that makes you feel like you know what you’re doing, even if you don’t.
Pair them with a crisp white Oxford shirt, sleeves casually pushed up. Add tailored navy trousers. Think less boardroom, more Nantucket weekend. This combination is clean, masculine, and hasn’t dated in about thirty years, which is pretty much the definition of timeless.
Where the Magic Happens
Here’s where JFK Jr. got really interesting. He mixed elevated basics with casual pieces in ways that shouldn’t have worked but did. A sport coat with a button-down and tie, sure, but then jeans and a baseball cap. Sweatpants and sneakers with a cable-knit sweater and scarf. There was a logic to the chaos, even when it looked chaotic.
Try this: take an outfit that feels too formal, then deliberately underdress one element. A wool vest with jeans and dress shoes. A polished sweater with sweatpants. The formula works because it’s honest. You’re not pretending to be one thing. You’re just wearing clothes.
Layering as Armor
Cold weather gave JFK Jr. permission to do what he did best: layer with purpose. Vests, scarves, sweaters, headbands, hats, coats. All of it had a reason.
The temptation is always to buy something new. Instead, try thrifting some accessories and layering them with what you already have. This is how you build style that’s actually yours, not just borrowed from someone else’s Instagram.
The Details That Actually Matter
Penny loafers. His father wore them. He wore them. There’s a reason they’ve survived this long in prep culture. They add intentionality to an outfit without you having to think about it. Get a good pair and move on.
Then there’s the sunglasses. Tortoiseshell Persols, or just blacked-out oval frames if you’re in a hurry. “Kennedy understood the power of a strong frame,” Volpe said. “It adds mystery in under two seconds.” Which is maybe the most JFK Jr. thing about his style. He understood that sometimes looking like you have somewhere better to be is the whole point.
The Real Secret
The most radical thing about JFK Jr.’s style in 2026 isn’t the clothes. It’s the discipline. He edited. He repeated pieces. He didn’t reinvent himself every season. In a world of viral fashion trends and algorithm-driven aesthetics, that’s basically revolutionary.
“That’s the real takeaway,” Volpe said. “Build a wardrobe that feels like you, then wear it like you mean it.”
The hard part isn’t finding the clothes. The hard part is having the confidence to wear the same thing again.
