JFK Jr.’s Iconic '90s Style Is Having A Moment — Here’s How To Dress More Like Him

It’s no contest: There’s never been a political scion that’s had more style than John F. Kennedy Jr. (Not that it’s much of a contest to begin with...Sorry, Jeb.)

Now that JFK Jr. and Carolyn Bessette Kennedy’s romance is being dramatized on the small screen in “Love Story,” a new FX series from Ryan Murphy, a whole new generation is discovering what minimalist style icons both Bessette and Kennedy were in the 1990s.

What worked about JFK Jr.’s style is that it never felt styled, said Chelsea Volpe, a fashion stylist and creative director. It felt lived in.

“He mastered that elusive balance of American polish and downtown ease — crisp shirting, relaxed tailoring, perfectly broken-in denim — but worn like he had somewhere better to be,” Volpe told HuffPost.

While much has been written about how to cop CBK’s sleek, Calvin Klein-heavy style, we thought we’d hone in on how to steal JFK Jr.’s look, because chances are that after watching “Love Story,” you either want to dress like him — or wish your boyfriend would.

As Volpe joked, “You can’t inherit Camelot, but you can borrow the formula.”

Go for soft tailoring over stuffy structured tailoring.

Kennedy understood proportion instinctively, Volpe said: broader shoulders, trim trousers, nothing fussy. As a recent auction of his wardrobe showed, the suits he favored were Armani or Calvin Klein, with an oversized fit and drape.

“There was restraint to his look,” the stylist said. “No over-accessorizing, no trend-chasing. Just great basics, great fit, and great posture.” (You might not have voluminous Kennedy hair, but you can always have good posture.)

Master the look with soft tailoring: menswear that swaps stiff padding and heavy canvas for lightweight fabrics and a natural, relaxed shoulder.

“A navy blazer, a well-cut charcoal suit, or even a knit tie instead of silk are great starter pieces,” Volpe said. “The key is ease. If it feels stiff, it’s wrong. His tailoring moved with him.”

Shop vintage.

No need to buy new to achieve this look. Looking for classic and timeless vintage items on eBay, DePop, Poshmark, or even your local thrift store is a fantastic way to find pieces that are actually of the ’90s era, said Jonathan Kirby, a fashion influencer and stylist.

“A simple eBay search for ‘Vintage Mens Ralph Lauren Sweater’ or ‘Vintage ‘90s LL Bean’ is all you need for a massive marketplace,” he said. “This is a great, sustainable way to have the best fit in town. Everyone will be asking you ‘Where’d you get that sweater!’”

Don’t be afraid to mix in something weird.

Go ahead and wear that Kangol flat cap, a plucky little beret or heck, even an exercise sweatband, to your next lunch date.

“JFK Jr. definitely was cashing in on his good looks and status when he’d throw a weird print or funky headband on. But consider him giving us all permission to be a little weird,” said Sophie Strauss, a personal stylist based in Los Angeles.

Invest in dark, straight-leg denim.

When it came to denim, Kennedy favored classic, unfussy jeans, Volpe said: mid-rise, straight-leg, no distressing.

“Dark rinse denim instantly looks intentional and grown,” she said. “Avoid skinny fits; JFK’s denim had structure.”

Get yourself an elevated white shirt.

Start with a crisp white Oxford or poplin shirt to nail the John-John look— slightly relaxed, sleeves casually pushed up.

“Pair it with dark denim or tailored navy trousers,” Volpe said. “It’s clean, masculine, and timeless. Think less boardroom, more Nantucket weekend.”

Throw a curveball into your dressy looks.

The core of JFK Jr.’s style was mixing elevated basics with more trend-forward, casual pieces, said Ashlyn Greer, CEO and founder of Fashivly, a personal styling company.

“Try out an outfit formula that mixes two casual items with an otherwise dressed-up look, like a sport coat, shirt and tie, mixed with jeans and a flipped-back baseball cap,” she said.

If you’re looking for just one item to add to your wardrobe, try a wool vest like this one from Filson, worn with jeans, a polished button-down, dress shoes and a baseball cap. (Your call if it’s a Yankees cap.)

Greer noted that another of his mix-and-matchy, iconic looks ― one that hasn’t appeared much in the FX show so far ― is sweatpants and sneakers paired with a more polished cable-knit sweater and scarf.

Learn to layer.

Cold weather is the perfect excuse to experiment with layering, something that JFK Jr. got down to an art form.

“He used vests, scarves, sweaters, headbands, hats and coats beautifully,” Strauss said. “It’s tempting to go buy a new pair of pants or shirt, but consider trying out some thrifted accessories first to layer with what you already have.”

Invest in a pair of classic penny loafers.

There’s a reason the penny loafer is a cornerstone of preppy style. (JFK Jr.’s dad, President Kennedy, was a fan of them, too) It’s an enduring classic that instantly elevates an outfit and provides a sense of intentionality.

“Many men will ruin an entire outfit by wearing the wrong shoes,” Kirby said. “Get a good pair of penny loafers to start and go from there. They at least go with almost everything.”

Don’t forget the shades.

Trailed by paparazzi in his daily life, Kennedy tried to salvage some privacy by slipping on sunglasses. They added some allure to his look, too, whether intentional or not. Tortoiseshell Persols work perfectly, or keep it simple with some blacked-out oval frames, like he wore while biking.

″[Kennedy] understood the power of a strong frame — it adds mystery in under two seconds,” Volpe said.

Repeat pieces and stay true to your taste.

What made JFK Jr.’s style iconic wasn’t the clothes; it was the discipline.

“He edited,” Volpe said. “He repeated pieces. He didn’t reinvent himself every season.”

In today’s world of quick-fire trends, there’s something radical about that kind of consistency. As Volpe put it, style isn’t about having more — it’s about refining what already works.

“That’s the real takeaway,” she said. “Build a wardrobe that feels like you, then wear it like you mean it.”