Style Guide: How to Nail JFK Jr’s Classic 90s Fashion

Yes, JFK Jr.’s ‘90s aesthetic is having a moment right now, thanks to the smash success of Prime Video’s Love Story: John F. Kennedy & Carolyn Bessette, the docuseries showcasing one of the most influential couples of the 1990s. Now, a new generation is discovering how effortlessly cool the prince of America’s style truly was, as Gen X and Millennials, old enough to remember, are reveling in it, as it has come full circle.

While his father may have dominated the political spotlight, and rightfully so, his son was dominating the quiet luxury look (as it’s known today), thanks to his heartthrob looks that were constantly the subject of paparazzi snapshots. 

Now being dubbed “JFK Jr.-Core” online, this look is more than just social media’s current fashion trend, as its making its way into national publications like GQ, Esquire, and even Vogue, which tells you this trend is more than a trend – it’s a style every man can master, and you don’t need Jr.’s jawline and chin to make it work. It’s a look that’s polished, yet never stiff, Ivy League athletic with a touch of prep, that doesn’t look pretentious. It’s an effortless masterclass at its finest.

John loved to mix and match his outfits, with his style roots being grounded in Ivy League prep, with a touch of athletic, which can look great jogging through Central Park, heading into a law office, or with a slight casual look in the office, just like Jr. did while working at George magazine. 

Here’s how to replicate the look and dress like John F. Kennedy Jr.

Style Your Hair like John F. Kennedy Jr.

If you’re ready to rock the JFK Jr. locks, you’ll need to grow it just a bit, as Jr. sported a medium-length style with just enough polish that kept his coif clean, yet lived in. It’s just long enough to show ample natural movement with good texture, while looking well-groomed and not unkempt. 

While his father rocked the close-cut, side-part with a touch of pomade (not the overly done, greasy look of the time) that he made famous during the ‘50s and ‘60s, Jr.’s length was more of a refined ‘70s shag, using just the right amount of product for a more put-together look. Start with a sea-salt spray on damp hair, then finish with a lightweight styling cream.

That combo will give it just enough hold, while allowing enough natural movement. If you have the hairline, you can style it backward, or a nice side-part swept back is another slight variation that works as well. Investing in a blow dryer will help you style your hair in no time, too.

Clean Up the Face and Jawline

Taking a note from his father’s playbook, Jr. opted for a clean-shave face – and with a jawline like his, why wouldn’t you? Keeping the face clean and neat helps to keep focus on strong facial features, giving that classic All-American look that works well in any setting, from the office to casual weekend errands.

The key is mastering the perfect shave, which requires learning your individual beard hair patterns and how to properly shave them for your face to avoid bothersome razor bumps and ingrown hairs. For some, that means avoiding blades and cartridges altogether. If that’s you, your next best bet is a foil shaver. If that is still irritating for your skin, you can always take your trimmer’s guards off and use the lowest setting. Go as low as you can, and you can’t go wrong.

Rock the Off-Duty Office Look

JFK Jr. may have had an uncanny ability to master the suit and tie (or tux when the occasion called for it) like no other, but it was his signature off-duty office look that many think of when recalling his style. The trick is putting in just enough due diligence that it looks effortlessly cool. Think simple and timeless. 

The look starts off with a classic white Oxford shirt in either cotton or linen for something better-wearing in summer. Next, you’ll want to pair it with khaki-colored chinos in a ’90s fit: relaxed, with a slightly wider leg opening – none preferably with a pleat. Next, a nice pair of leather loafers rounds out the footwear, and you can add a braided leather belt, while a loosened pennant-style tie is a nice touch. To finish out the look, an unstructured blazer in a timeless colour such as navy or tan is as versatile as they come. If you need an extra layer for colder weather, a quarter-zip sweater is the way to go.

The Weekend Athletic Wear You Can Sport all Week Long

As much as JFK Jr. loved to work out, so too did the papp love to photograph him doing so, especially when it was in Central Park. While going shirtless in navy or white shorts is about all you need to do while playing ultimate frisbee (if you want to do as John did), here are a few other staples he was fond of.

Start with a plain white tee and keep it super simple: no logos or graphics, and a fit that’s not too loose or tight – a classic cut. For those chillier days, you can sport a nice-fitting knit sweater over the top. On the bottom, some above-the-knee athletic shorts are the way to go, or some sweatpants with an elastic cuff (not the knit cuff of joggers) will work too. For footwear, you can rock some sneakers like vintage-inspired pairs from New Balance or Asics. The final finishing touch that became synonymous with his relaxed looks is a cotton baseball cap, always worn backwards. 

Mix and Match the JFK Jr. Way

The truly nice thing about the two looks is that you can pretty much wear them all interchangeably. Its one of the underrated aspects of his fits and why everyone still loves it today. The trick is putting in the effort without overdoing it. The brilliant thing is that the off-duty office look and the athletic weekend wear are meant to blend.

Throw on a backwards cap with your business suit. Try a white tee with some sweatpants, then throw on a blazer, and you’ll be amazed at how well it works together. Or go quarter-zip with chinos and pair them with some New Balance sneakers, and you have the ultimate business-casual look you can wear to the office and drinks afterward. The combinations are endless, just make sure not to overthink it, but know that nothing is accidental. 

The beauty of this look is that you ultimately need fewer than 10 articles of clothing and can create almost limitless style combinations. Even though the JFK Jr.-core look might be trending, it’s also timeless and won’t go out of style. It’s an understated confidence that says you have style, and no, you don’t need to try too hard – just like JFK Jr. himself.

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Love Story is available in Australia on Disney+, with the finale set to drop on March 27.

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