So FX dropped “Love Story,” Ryan Murphy’s dramatization of JFK Jr. and Carolyn Bessette Kennedy’s romance, and suddenly everyone’s scrolling through eBay at midnight looking for vintage Armani blazers. Fair enough. The man had style in spades.
Here’s the thing though: JFK Jr.’s look wasn’t about having money (well, he had money, but that’s beside the point). It was about restraint. It was about understanding that sometimes the most powerful statement is knowing when to stop adding things.
“You can’t inherit Camelot, but you can borrow the formula,” as fashion stylist Chelsea Volpe put it. And honestly, that’s the entire game right there.
The Philosophy Behind the Fit
What made Kennedy’s style tick wasn’t trend-chasing or logo-collecting. It was the opposite. He mastered that balance between polished American preppy and downtown cool, the kind of thing that looks like he threw it on without thinking but actually required a lifetime of good taste.
The man understood proportion. Broader shoulders, trim trousers, nothing fussy. No over-accessorizing. No reinventing himself every season. Just great basics, great fit, and apparently, impeccable posture.
“His tailoring moved with him,” Volpe explained. “If it felt stiff, it was wrong.” That’s the memo right there. If your clothes feel like armor, you’re doing it backwards.
Start With Soft Tailoring
Forget structured, heavy-canvas suits that feel like you’re wearing a cardboard box. Kennedy favored Armani and Calvin Klein with an oversized fit and natural, relaxed shoulder. Navy blazers. Charcoal suits. Knit ties instead of silk. Pieces that breathe.
A crisp white Oxford shirt, sleeves casually pushed up, paired with dark denim or navy trousers. That’s your starting point. Think Nantucket weekend, not boardroom power play.
The key is ease. Real ease, not the kind that comes from expensive fabrics. The kind that comes from actually living in your clothes.
The Vintage Route Makes Sense
Here’s where the math actually works in your favor: you don’t need to drop thousands on new designer pieces. Fashion influencer Jonathan Kirby points out that vintage shopping on eBay, Depop, or Poshmark is where the real finds live. Vintage Ralph Lauren sweaters. 90s LL Bean pieces. Actual items from the era that actually fit the aesthetic.
“This is a great, sustainable way to have the best fit in town,” Kirby said. Plus, everyone will ask where you got that sweater, which beats the alternative where they ask why you’re dressed like a catalog.
The Art of Mixing Up
Kennedy never wore one vibe the whole time. He mixed elevated basics with trend-forward casual pieces. Sport coat with jeans. Tailored shirt with a flipped-back baseball cap. Sweatpants with a cable-knit sweater and scarf. The formula was simple: take something dressed up and knock it down with something casual, or vice versa.
A wool vest works. Penny loafers definitely work (they’re iconic for a reason, and his dad wore them too). Dark rinse denim with structure. Straight leg, mid-rise, no distressing.
Layering Is Your Secret Weapon
Cold weather is basically permission to experiment. Vests, scarves, sweaters, headbands, hats, coats. Kennedy used them all beautifully, and here’s the radical part: you can thrift most of it. Before you buy new pants or shirts, grab some layering pieces from your local thrift store and mix them with what you already own.
Sunglasses matter too, in a weird way. Tortoiseshell Persols or blacked-out oval frames add mystery. They added allure to his look, whether intentional or not. “Kennedy understood the power of a strong frame,” Volpe noted. “It adds mystery in under two seconds.”
The Real Discipline
What people miss about JFK Jr.’s style is that it wasn’t about having more clothes. It was about editing relentlessly. He repeated pieces. He refined what worked instead of constantly starting over.
In a world of quick-fire trends and endless shopping apps, there’s something genuinely radical about that kind of consistency. Building a wardrobe that feels like you, then wearing it like you mean it, is the actual flex.
Style isn’t about being different every day. It’s about being so sure of yourself that you can wear the same outfit twice without anyone noticing.
