The style lessons John F Kennedy Jr taught us that still work today
John F Kennedy Jr (pictured here with wife Carolyn Bessette Kennedy) often wore a backwards baseball cap and sunglasses - Shutterstock Editorial
Fashion fans have been keenly anticipating the release of each weekly episode of Ryan Murphy’s latest TV series, Love Story. Airing on Disney+, the show has looked back at the romance – and tragic death – of political scion John F Kennedy Jr and his wife Carolyn Bessette Kennedy (CBK) over the space of nine episodes, with the final instalment airing this week.
And while the fashion world’s interest is usually in CBK – whose minimalist 1990s wardrobe of slip skirts, white shirts, loafers and straight leg jeans is still on designers’ moodboards today – her husband’s style was equally as influential. Indeed, JFK Jr was known for looking particularly good in a tux, with an auction of his Calvin Klein two-piece suit and Giorgio Armani overcoat raising thousands of dollars at auction in 2024, while his preppy style has also served as inspiration for designer Jonathan Anderson.
Just as stylish in his weekend casuals – whether photographed on his bike, or walking his dog – his was a cool, laidback and effortless aesthetic, one which showed he was unafraid of breaking fashion rules.
“I believe that the reason Mr Kennedy Jr’s style resonates so heavily is because it was both timeless and ‘of the time’ all at once,” says menswear stylist, Daniel Johnson. “Look at any outfit he wore and you can in some ways see yourself wearing it now, 20 years ago or even in 10 years time. The reason for this in my opinion is that his style is relatable because it’s not unachievable, it’s not overly polished nor is it unconsidered. It feels like if you wanted to achieve the same look, you absolutely could do so with little effort, although very few often do.”
Here, we break down seven of his key looks, with tips on how to emulate them today.
The biking around town look
Sporting a business casual look for his commute to work in New York City (c.1990s) - Lawrence Schwartzwald
“You can’t summarise Mr Kennedy Jr’s style better than this image does,” says Johnson. “He’s added boots to what otherwise looks like a non-descript everyday business casual style, rolled the trouser leg up and got on with his commute. Anyone else in his position would have put on a pair of brogues or loafers and hopped in a yellow cab. The sunglasses just go one step further in adding an element of nonchalance.” The 1990s style mini-sunnies are actually back out of fashion for 2026, so switch for a more on-trend pair of Rayban Wayfarers instead, and you could also go for full legs-out appeal with a pair of shorts, à la Paul Mescal.
The laidback all-white look
Confident in cream and white in New York (1995) - Lawrence Schwartzwald
Not many men are brave enough to go for cream-coloured trousers, but JFK Jr pulls them off thanks to his brown accessories, particularly the belt, which breaks up the tonal look. “The fit of the trousers is relaxed but not baggy so as to hide his shape,” Johnson says. “This is a great example of clothes put together well and worn with confidence in classic colours. There’s no flash watch or accessories – instead he relaxes the formality of the yacht club look with a baseball cap and sunglasses.”
The dog walking ensemble
JFK Jr was just as stylish in his weekend casuals (c.1990’s)
Wearing joggers, running shoes and a cable knit, this might appear to look like JFK Jr threw on whatever was nearest to him when heading on a dog walk, but for Johnson it’s a great example of how he styles outfits to appear cooler. “The difference is subtle, a few touches of nonchalance,” he says. “The cap backwards and a loosely tied scarf show he’s not trying hard to over-do his outfits. Most importantly, he’s incredibly comfortable in himself and it shows in the clothing.”
The brunch look
Nailing the laidback vibe for a brunch date with his wife, CBK, in New York (1997) - Lawrence Schwartzwald
Sure, there are things about this outfit that feel like they should stay in the 1990s (the Zoolander-esque sweatband, for one) but there are other redeemable qualities to it. Continuing to prove that you can pair brown with black, JFK Jr nails the smart-casual vibe of brunch at Bubby’s with a waist coat worn over a graphic print shirt with the sleeves rolled up and the collar tucked in, which gives it a laidback appeal. A modern take on this look would be to wear a knitted vest over a shirt instead, and swap the brown pleat front trousers for jeans. Newspaper and arm cast optional.
The smart-casual look
Taking classic menswear staples and making them look more relaxed (1997) - Lawrence Schwartzwald
Wearing a brown wool collarless coat, simply buttoned up, plus a grey scarf tucked in and a black beanie, there is something especially New York coded in this outfit for Johnson. “He’s taken an otherwise classic menswear staple formula of Chinos and a blazer but made the overall look much more relaxed by accessorising with boots and a beanie hat – plus accompanying bandage,” he says. “The mix of formalities is for me what New Yorkers do so well and which Mr Kennedy Jr embodied.”
With his man bags
JFK Jr demonstrates how to accessorise with Italian leather bags (1997) - Lawrence Schwartzwald
Succession’s Tom Wambsgans might have derided the “ludicrously capacious bag”, but as David Beckham demonstrated last month with his new Hermes Haut à Courroies, every modern man needs one. It’s something JFK Jr knew back in 1997, as seen here with two Italian leather bags – one in tan, one in black. As ever, JFK Jr has fun with his accessories, injecting some pizazz into an otherwise hum-drum look, with a mustard-coloured tasselled scarf and a navy beatnik hat. To bring this look into 2026, switch the hat for a beanie (all over the Milan menswear runways recently) and opt for a wider scarf – blanket styles are currently trending.
Co-ordinating with his wife
His scarlet knit and the hem of his hat perfectly matches his wife’s red Prada coat (2000) - Evan Agostini
Matching couples style is nothing new, but we love the subtle nod to it here, with JFK Jr’s scarlet knit and the hem of his hat perfectly coordinating with CBK’s red Prada coat. Think of it as the winter version of matching your tie to your wife’s dress at a wedding. Other things of note in JFK Jr’s outfit here include his decision to ignore the no black with brown rule, which works because he’s incorporated other colours into his look. Colour pop accessories are an easy way to emulate this style today – think a red or purple scarf or hat.
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