Thanks to the recent release of the American biographical romance anthology television series, ‘Love Story’, the masses are finally waking up to the incredible dress sense of the late John F. Kennedy Junior.
Those who have spent any time down the rabbit holes of menswear Tumblr archives, carefully curated Pinterest boards, or the more esoteric corners of Instagram moodboard culture will know that JFK Jr.’s laid-back take on prep has been on trend for years. Long before the algorithm rediscovered him, he already held cult status among style obsessives who understand that the best outfits rarely look like outfits at all.
In our eyes, what makes JFK Jr’s looks so compelling is their normality. The most enduring images of Kennedy are the grainy, slightly overexposed paparazzi shots of him pedalling through Manhattan traffic on a mountain bike, a creased dress shirt billowing in the wind, wide pleated pants around his waist, battered leather sandals on his feet, and irrefutably ’90s eyewear shielding him from the midday glare.
It’s the kind of laid-back prep that oozes ’90s New York. Smart pieces worn for book-signings paired with his favourite Californian streetwear labels. Everything’s worn a bit loose, and nothing is ever too polished. The shirt isn’t tucked perfectly, the trousers are baggy, and the sandals look like they’ve seen more than a few summers. But that’s exactly what makes him one of the most inspirational style icons of all time – nothing looks overly styled, deliberate or try-hard.
The ironic part of all this is that JFK. Jr would never have read anything resembling a style guide, but for us mere mortals, extra help is needed. So here’s a list of the most laid-back, prep-inspired garments we could find to pay tribute to one of Pinterest’s most shared men of all time.
The KAVU Strapcap isn’t just the sort of thing John F. Kennedy Jr. might have worn – it’s something he actually did wear, and fairly often from what we can make out. The good news is that KAVU still makes them today, and they’ve changed very little (if at all) since the ’90s.
thisisneverthat Flannel Hooded Check Shirt
To balance out all the sober tailoring he had to wear during the working week, Kennedy often leaned into pattern whenever he was off duty. Flannel was clearly a favourite – usually worn slightly loose and layered over a T-shirt or under a jacket. This hooded check shirt from thisisneverthat feels like exactly the sort of thing he’d have thrown on during a crisp New York fall.
We can’t say for definite (the logo is too grainy to make out), but we’re pretty sure that JFK Jr owned a pair of Patagonia Baggies shorts exactly like this. And who could blame him? Baggies have rightfully earned their place in the shorts hall of fame – equally suited to hot evenings in the city as they are to long, lazy weekends out in the Hamptons.
From what we can tell, John F. Kennedy Jr. wasn’t exactly a fan of shoes. When he wasn’t in dress shoes, he was barefoot – and when he wasn’t barefoot, he was in sandals. These Chaco Sandals, with their unmistakably ’90s patterned straps, are exactly the kind of pair he would have reached for.
Comfort clearly came first for John F. Kennedy Jr., which is probably why he avoided stiff, formal dress shirts whenever he could. He favoured lightweight, breathable cotton instead – just like the soft, airy fabric of this TDR Button-Up.
The only thing John F. Kennedy Jr. seemed to collect more eagerly than mountain bikes was patterned knit beanies. Once the temperature dropped below 10°C, he was rarely seen without a bold, cosy cap – much like this playful, knit beanie from Khakis.
thisisneverthat Pattern Knit Crew
Patterned knits made by the likes of Coogi & co. were everywhere in the ’90s, and JFK Jr didn’t shy away from his fair share. This thisisneverthat one is just the right level of restrained – mad enough, but not tipping over into optical illusion territory.
adsum 3/4 Zip Knit Pocket Sweater
The 3/4 zip is the perfect middle ground between casual and formal – a solution JFK Jr. seemed to figure out early on in life. This one from Adsum is inspired by a classic Patagonia design, nicely celebrating both the era and the quality of the original.
When John F. Kennedy Jr. wasn’t in shorts, he tended to reach for loose-fitting trousers – often pleated and frequently in a lighter shade. This pair from South Korean brand Khakis fits the bill perfectly.
Without a doubt, John F. Kennedy Jr.’s favourite off-duty pastime was cycling around New York City. Over the years, he was spotted on an array of different bikes, and almost always paired them with some kind of super ’90s eyewear – just like these Oakley Neo Jacket Sunglasses.
All of our favourite JFK Jr. outfits have that effortless, “thrown-on-entirely-for-comfort” aesthetic – and when it came to shoes, that often meant a pair of cushioned running trainers. He wore everything from Nike to Adidas, but he was repeatedly spotted in Asics – just like these Gel Kayanos.
Very few people possess the level of steez required to look good in a backward baseball cap, but JFK Jr was one of them. This Khakis cap fits the ’90s prep look, and comes in a very apt khaki colour pallette.
Still By Hand Linen Mixed Wide Shorts
Just like his trousers, John F. Kennedy Jr. favoured shorts with plenty of room to move. This pair from Still By Hand delivers exactly that – width in abundance, plus the all-important pleat.
Closing out the list is one of the most quintessential JFK Jr. pieces of all time: the Kangol Wool Cap. Honestly, we don’t think anyone ever wore one quite as good as he did – so save yourself the embarrassment and just enjoy it from afar.
