For mere mortals, the Kennedys have always held something of an allure.
America’s first family were incredibly wealthy, privileged and good-looking — and yet, also dogged by tragedy, which came to be known as the ‘Kennedy Curse’.
John F Kennedy became America’s 35th President and was infamously assassinated in 1963. His brother Robert was also assassinated in 1968. And his son, John F Kennedy Jr., dominated tabloid coverage throughout the Nineties in the closest thing America had to a prince, before dying in a plane crash in 1999, alongside his wife, Carolyn Bessette Kennedy.
Though their premature deaths were shocking, they came at the culmination of a turbulent seven years for the couple, which Ryan Murphy has turned his hand to immortalising in FX’s latest TV show, Love Story: John F Kennedy Jr. & Carolyn Bessette.
If you’ve not seen this splashed all over your feed (educating an entire generation on who these latter-day celebrities actually were), then allow me to educate you. The pair met in 1992, while Carolyn was working as an assistant to Calvin Klein. In 1996, they married, and from then on, every facet of their relationship was scrutinised by the press.
While fans have been fawning over Carolyn Bessette Kennedy’s minimalism style — comprising many all-black looks and the Narciso Rodriguez bias-cut satin slip dress she tied the knot in — I’ve got another fashion icon in my sights. Namely, her husband.
Because JFK Jr. is a bit of an unsung hero when it comes to putting together a good ‘fit, and people are starting to recognise it: last week, New York City saw the first ever JFK Jr. lookalike contest, in which the contestants wore suits, tiny shorts, and even rollerblades in a bid to win the title of “biggest hunk” (complete with a $250 prize).
While his wife has gone down in history as one of the style muses of the late 1990s, JFK Jr. was no sartorial slouch either. His take on the preppy, Ivy League dressing still holds up — I’d argue even more so, given that the 90s and Noughties are now back in a big way.
For the curious, that means button-down Oxford shirts, crew neck sweatshirts that wouldn’t look out of place on a sailing (or rowing: pick your upmarket sport of choice) team, and maybe even a V-neck vest or two. Want to go full JFK? Rock any of the above with a pair of tortoiseshell glasses, a backwards cap, or an Abercrombie & Fitch-style jumper.
For those wanting to emulate his laid-back style, here’s your starter kit for channelling all things Kennedy.
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Charles Tyrwhitt Poplin Shirt
A good starting point for all things preppy is a good white shirt.
JFK Jr. was a big fan of a classic suit, and was often spotted wearing a white shirt and tie for business meetings. Channel the same style with this Charles Tyrwhitt number: simple, classic, flattering.
Buy now £32.95, Charles Tyrwhitt
Liberty Floral Geo Madder Silk Tie
Pair that shirt with a good old-fashioned tie. If you’re really leaning into the whole 90s aesthetic, then this number from Liberty works nicely. A flattering print, a nice corporate vibe, and (importantly) it’s all in silk. Style it slightly undone for an off-duty look.
Buy now £160.00, Liberty
Marks & Spencer Cotton Blend Ribbed Half Zip Jumper
Quarter and half-zips are having a moment now, but you’d best believe that they were the preppy man’s style of choice back in the 90s, and until recently, finance bros too. Both practical and chic, this number from Marks & Spencer can be zipped all the way up to the top or left slightly undone for a more casual look.
Buy now £38.00, Marks & Spencer
Josef Seibel Earl 08 Leather Chelsea Boots
The ultimate practical investment. The Chelsea boot works wonderfully both as a work shoe (to go with all those suits and patterned ties you’ll be buying) and a casual shoe, to be paired with some scruffy Levis and a crewneck sweater. These ones are crafted from leather, the better to last you for years.
Buy now £120.00, John Lewis
Seasalt Cornwall Men's Balefire Original Polo
Nothing says off-duty (at least, in the world of American old money) like a polo shirt. You’ll be wearing it for early morning walks by the sea, yes, but also to play tennis in that tennis court you definitely own. Either way, it’s a must-have, and this number comes in a gorgeous shade of duck-egg blue that pairs well with both chinos and shorts.
Buy now £35.95, Seasalt Cornwall
Marks & Spencer Lambswool Blend V-Neck Knitted Vest
Need to keep warm but still look good? This V-neck vest is the perfect piece to layer over a button-down shirt, a t-shirt or tucked away under a jacket.
To that end, Marks & Spencer can’t be beat: not only is it outrageously good value, it’s also made from a lambswool blend that will stand up against all those chilly New York (or, um, London) nights.
Buy now £11.39, Marks & Spencer
Brian Oak London Navy Green Striped Rugby Shirt
We still don’t really know if Americans know what rugby actually is, but they sure do love a striped rugby shirt — and it definitely fits the preppy aesthetic.
Whether or not he knew about (or was a fan of) this rather excellent sport, it certainly feels like something JFK Jr. might have worn, and either way, stripes look flattering on everybody.
Buy now £38.25, Debenham's
Passenger Men's Escapism Sweatshirt
We’re living through a 90s revival period, and quite right too. The Nineties’ take on sweatshirts and t-shirts (that is, boxy) still looks great as a style choice today, and outwear brand Passenger is a good place to shop for both.
Top of the list: this lovely crewneck sweatshirt that manages to be both hardwearing and rather fetching. Wear with cargo shorts and flip-flops for the ultimate beach day look.
Buy now £54.95, Passenger
Abercrombie & Fitch Graphic Crew Sweatshirt
In a similar vein to the above, channel a relaxed, JFK Jr.-at-home vibe with this loose-fitting sweatshirt from Abercrombie — which comes either in a light heather grey or in red, with a Saint Moritz logo (for ski fans).
Buy now £65.00, Abercrombie & Fitch
Ray-Ban Clubmaster Classic Glasses
Sleek, stylish and understated: what look would be complete without a pair of ultra-American sunglasses?
These tortoiseshell glasses, from Ray-Ban, look strikingly similar to a pair that the costume team picked out for Paul Anthony Kelly, who plays JFK Jr. in the show, and for good reason.
They go with pretty much everything, and look much more casual than an all-black frame.
Buy now £155.00, Ray-Ban
Kangol Flat Cap
The real JFK Jr was a fan of a Kangol cap, so naturally, I had to include it in an edit celebrating his style.
More casual than the fedoras or structured hats that many of America’s elite favoured, JFK Jr.’s dedication to ‘sloppy chic’ saw him papped multiple times wearing a Kangol. As with the baseball caps, wear yours reversed for extra authenticity.
Buy now £49.95, Amazon
IDEA Marry Me Hat
If it’s good enough for Harry Styles, it’s good enough for us.
The pop star was spotted in a hat from concept store IDEA last year, and while we’re not saying you should go for exactly this version (though it does feel very apt if you’re channelling Love Story vibes), the baseball cap has been a staple for men everywhere for decades now.
JFK Jr. was well known for wearing his backwards, so flip it for extra authenticity.
Buy now £40.00, IDEA
Brompton C Line - 12-speed
JFK Jr. was often tooling around Manhattan streets on a bike. He swapped between a few brands — plenty of opportunity to try new ones given his habit of forgetting to lock up his rides — including TREK, Peugeot, Cignal and GT.
Here in the UK, Brompton is our city bike of choice. It's compact, foldable, available in a slew of colours, and comes with 12-speeds, giving your wheels serious range — Abha Shah
Buy now £1599.00
