SHANE WATSON: As a new TV series launches on the doomed romance of JFK Jnr and Carolyn Bessette-Kennedy… why no one can truly capture the effortless chic of America’s tragic style icon

It may have been the autumn fashion collections in New York this weekend, but the most hotly anticipated event was off the catwalk and showing on Disney+. 

‘Love Story: John F. Kennedy Jr and Carolyn Bessette’ is a fictionalised drama series about the iconic couple’s courtship and turbulent marriage in the mid-Nineties – and the fashion world in particular has been desperate to see it.

The story is ripe for TV. Kennedy, the only surviving son of JFK and Jackie, was American royalty and once voted People Magazine’s Sexiest Man Alive. They were the golden couple of the hour who died young after less than three years of marriage, side by side in a plane piloted by JFK Jr.

And Carolyn Bessette-Kennedy (better known as CBK) was not just a beauty and fashion icon in her lifetime; she has remained the supreme poster woman of minimal New York Nineties style.

Which brings us back to the reason why this show is so eagerly awaited and why the producers chose to launch it at New York Fashion Week: her look is so much in vogue right now that any one of her minimalist outfits could appear on the runway today.

It’s possible that American producer Ryan Murphy (who brought us Glee and American Horror Story) didn’t quite appreciate the level of interest in CBK, specifically the nuances of her style, when he embarked on this project – but he does now.

When pictures from the set were released last summer, there was outrage among fashion watchers who were appalled to see the actress playing CBK wearing clothes (namely a cheap-looking leather blazer, copper-coloured satin slip skirt, and Converse high tops) that everyone agreed the real CBK wouldn’t have been seen dead in.

After the firestorm, Murphy admitted he might have underestimated the cultural significance of CBK, but protested that the clothes had just been stand-ins for test shots and that they were going to great lengths to get the looks right from that point on. This included sourcing the original Yohji Yamamoto ruffle skirt she wore with a white shirt to a fundraiser, making her Narciso Rodriguez wedding slip dress from scratch, and distressing the right Birkin bag (the No 40 style owned by CBK, not the 35 as featured in the test shots) to give it the necessary ‘lived in’ feel.

History doesn’t relate whether in hindsight Murphy regrets taking on the challenge of bringing this story to the screen – he probably anticipated some complaints from Kennedy admirers but never bargained for incurring the wrath of fashion lovers – but one thing’s for sure; he’ll have come out the other side of this project realising that there’s nothing on earth harder than faking immaculate minimalism, CBK’s signature.

Even tougher is recreating that look now, when it is riding as high in the fashion charts as in her heyday. In her lifetime, CBK had many admirers, but now there is a generation of new fans drooling over her style.

To understand the impact of CBK on the fashion psyche, you need to rewind to the mid-Nineties when she was a 20-something working in New York for Calvin Klein as a publicist, and the perfect clothes horse for his clean American aesthetic.

This was the era of the slip dress and high-heeled strappy sandals, when less was more, It-girls were in the news, and a beautiful, well-connected young woman could make headlines for walking out of the right club looking fabulous.

Bessette, with her long, glossy blonde hair, flashbulb smile, athletic model figure, and impeccable sense of style, was already a cool young woman when she started dating JFK Jr in 1994. By the time they were married two years later, she was 30 and a fashion icon on a par with her mother-in-law, Jackie Kennedy, in her day.

CBK was pictured wherever she went, whether it was walking the dog (black tank, bootcut jeans, block heel sandals), shopping in New York’s Tribeca (black turtleneck, toffee cords, brown loafers), or arriving at a black-tie event in that plain white shirt and black ruffled Yohji Yamamoto skirt, no jewellery, hair loose.

But in terms of fashion nous, she was ahead of her mother-in-law, Jackie. CBK reinvented what it meant to look elegant, chic, relaxed, and contemporary at the same time. She wore wool beanies with tailored Prada coats and sandals with bootcut jeans.

She wore occasional splashes of colour – a red subtly checked coat, yellow loafers – with black and beige and cream and denim, but not prints. She almost never wore jewellery, and barely any make-up, bar dark red lipstick.

On her wedding day, she married in an ivory slip dress with her hair tied back in a sprouting bun. Under her watch, simple American style was given an extra edge and polish, and it never looked better. All the components of what we now think of as polished dressing were originally assembled by CBK.

She championed the rule of buying better – and less – and mixing classic items with edgier pieces. (She had a passion for Yamamoto’s structured designs and wore a Pierrot ruffle-fronted black coat with beige lining and matching trousers by the Japanese designer).

She was an early adopter of taking jeans seriously and wearing them clean and pressed (bootcuts or straight legs); she liked mixing different textures together and changing the mood of clothes with a scraped back ponytail, or a tight bun and a tortoiseshell hairband, or – to offset the simplicity of a plain, fitted, monochrome dress – loose natural hair.

She always looked groomed but never stiff or severe, and she believed strongly in the power of a tailored coat to elevate everything.

Something else about the CBK look: she could have been wearing almost all of it – bar the slip dresses – today, in 2026, approaching her 60th birthday. There were no high hemlines or skin-tight trousers or sheer fabrics in her wardrobe – everything was eminently wearable and would have stood the test of time.

By all accounts, Ryan Murphy’s production team moved heaven and earth to find copies of the clothes she wore (the sunglasses will not have presented a problem since her signature style – Aldo by Selima Optique – is still going strong) and to recreate her look as authentically as possible, but in the end, it’s an impossible task.

While Paul Kelly is a dead ringer for JFK Jr, the actress Sarah Pidgeon is not much like CBK. No great surprise, really. Bessette was a dreamy-eyed, 5ft 9in beauty with a fabulous athletic figure and an extraordinarily thick mane of hair, dyed to a glossy, bright blonde that was a critical part of her look. Back during Bessette-gate last year, even Carolyn’s hairdresser felt compelled to add his voice to the screams of horror, saying in an interview: ‘Totally wrong… why is she all ashed out with her hair only one colour?’

And it’s not just the colour that’s not quite right. Pidgeon’s hair in the show is a wig, but still, it’s too thin, too messy, and not New-York-show-pony enough. And the clothes – despite the fact Murphy put together a ‘style advisory board’ of ten fashion specialists – look similarly insubstantial.

Yes, her much-worn Manolo Blahnik patent Callasli sandals are in there, but the black slip dress they’re worn with looks like H&M – not the knockout glove-fit number it was on her. Yes, the remade Narciso Rodriguez wedding dress looks identical, but it doesn’t sing as the original did on Bessette; it doesn’t glow and slide over her perfect figure in the same way.

The oversized white shirt that looked so bright and special on CBK on so many occasions looks waitressy on Pidgeon, and the Yohji ruffle shirt seems to have lost its bounce.

In one scene, we see her walking down the street in bootcut black jeans, a sweater, and loafers – none of which you can find fault with – but the effect is ordinary and unremarkable, whereas in real life, CBK would have turned heads. That was the whole point.

Maybe the trouble is that these simple clothes can look ordinary unless they’re worn by a thoroughbred racehorse, or maybe Pidgeon is too slight and doesn’t fill them up and do them justice. Either way, when the New York front row sees Love Story, they’re going to be very disappointed. There’s not a trace of the CBK magic or style in this clunky characterisation.

Sadly, anyone hoping for tips on how to wear classic Nineties minimalism to maximum effect – with the style and flair that brings them alive – will have to settle for trawling the internet for 30-year-old images of the one and only Carolyn Bessette-Kennedy.