The quest to look effortlessly and timelessly elegant is a mission shared by countless women. The fact that, in 2023, it’s still a socialite famous for just a few years in the 1990s who represents the zenith of getting this right exemplifies just how difficult it is.
Carolyn Bessette Kennedy, the wife of John F Kennedy Jr, was in the public eye for a remarkably short period of time – from the early 1990s when she was a key player on New York’s social scene, as a publicist for Calvin Klein, until her untimely death alongside her husband in a plane crash in July 1999.
Yet CBK, as she was known, created a disarmingly minimalist yet sophisticated look which is still inspiring designers and forming a template for modern, low-key dressing today. “Carolyn is a real enigma. I don’t want to objectify her, but she’s like a work of art,” says Sunita Kumar Nair, the author of a new book, CBK: Carolyn Bessette Kennedy: A life in fashion, which looks in forensic detail at CBK’s wardrobe, speaking to some of those who knew her attitude to style best.
“It was beautiful to hear about how she garnered relationships with designers in quite an old-school way,” Nair continues. “She always wore Manolo Blahnik shoes because she adored the man, the stores and the products. It was similar with Yohji Yamamoto, Prada and Ann Demeulemeester.”
This is a style strategy which is unreachable for most of us, but Nair emphasises that “Bessette Kennedy created this relationship and loyalty which I find very inspiring, especially when you look at so many celebrities today who have this very cut-and-paste style which is so driven by trends, sponsorships and stylists. It feels more honest.”
She also used fashion in the same way so many of us do – to form a kind of armour to give us confidence – in her case, against the huge amount of press attention which her marriage to one of the world’s most eligible men had garnered.
“She had never entertained the idea of being famous,” says Nair. “Her friends often told me that it was a point of unease for her so clothes helped her to feel empowered.
“She preferred to never complain, never explain in spite of the huge amount of scrutiny she was under,” says Nair.
So how can you feel empowered the CBK way? These are six cornerstones which formed her insouciantly luxurious look which so many still aspire to master today.
1. Find your perfect white shirt
“Kennedy was a master stylist,” notes Nair. Indeed she is a poster woman for the adage that it’s not what you wear, but how you wear it. Case in point: the white shirt. “They were an item she was very habitual about and she’d wear them both for casual and evening. I think their versatility made her confident,” Nair explains. “Her friends said she’d wear them back in college and would always be laughing and at ease in them.”
The best-known – and most imitated – example of Kennedy’s white shirt styling is her appearance at a fundraising gala for the Whitney Museum in March 1999 when she paired a slightly oversized white shirt – cuffs folded up and the top few buttons undone – with a long black maxi skirt and strappy sandals. It was a look so pared-back that its beauty was in having the self-possession to be that “underdressed” for what might once have been a ball gown-worthy event. “There’s a poetry to her wardrobe, everything has the same theme. It’s a melody,” says Nair.
Whether you wear yours formally with a skirt or trousers or more casually with jeans, it’s the undone styling which transforms something potentially boring into a compelling outfit.
Get the look
Organic cotton shirt, £250, Serena Bute; Poplin shirt, £95, With Nothing Underneath
2. Create your own version of sporty
Athleisure has dominated our wardrobes for the past decade, but Carolyn and John did a moneyed, preppy take on the look which is just as appealing now.
“JFK had already embraced that sort of style but friends told me that before she met him, Carolyn had never owned a pair of trainers,” says Nair. “They really epitomised sportiness as a lifestyle, dashing out to the shops in Stan Smiths or Air Max. They were really active people, often kayaking or playing frisbee.”
Whether they were in New York or Hyannis Port, the Kennedy’s country retreat, the couple did throw-on, relaxed dressing with all the same elan of their most formal moments – key pieces included chunky trainers, zip-up fleeces and loose joggers.
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CBK’s approach to make-up was as minimalist and refined as her clothing but if she ever ventured into maximalist territory, it was with her lipstick. For several evening occasions she chose to finish her black or white outfit with just a bright slick of red lipstick. Even dazzling jewellery – of which she had plenty to choose from – was kept to an absolute minimum, a lesson in impeccable restraint.
Get the look
Rouge Coco lipstick in Carmen, £37, Chanel; Le Duo Rouge liquid matte and sheer balm in Amour Fou, £53, Violette Fr
4. Always belt and button your coat
In another example of Kennedy’s style impact being more about the how than the what, Nair observes that “she always wore her coats buttoned and belted” because “she really appreciated the silhouette of everything”.
Sure enough, studying pictures of Kennedy shows that she was very rarely photographed with her coats anything other than precisely done all the way up, creating a neat and polished counterpoint to the current vogue for slouchy layers. As a zero cost way to look and feel instantly (literally) pulled-together, this is it. You could even add a belt to a coat which doesn’t have one.
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The fashion spotlight has shone on dresses a lot in the last few years but this season’s quiet luxury focus has shifted the conversation back to separates, which was a specialist subject for CBK. “It’s important that she was such a champion of separates which evokes a really intelligent conversation with so many people,” says Nair.
“You may love her midi skirts, but then pair yours with a printed shirt which she wouldn’t have done. She speaks to so many of us in different ways.”
Indeed, CBK’s instincts skewed towards the plain so you were most likely to find her in a neutral polo neck or sleeveless top with her midi. Nair muses that this might have come as much from her husband’s family, equally venerated and mythologised for their style credentials, as her own predilections. “Lee [Radziwill, his aunt] and Jackie [Onassis, his mother, who died in 1994] were so important to her and they weren’t fans of print so if she did it, you know she’d really thought about it.”
Get the look
CBK’s icy blonde hair undoubtedly made every outfit she wore look better, whether it was scraped back into a sleek bun or left to tumble around her shoulders. Her penchant for one very specific hair accessory – the tortoiseshell headband – served to emphasise its gloss and gleam.
The headband was a shortcut to conjuring CBK nonchalance then as much as it is now. “A lecturer at Central Saint Martins said that many students still reference Carolyn in their collections now,” says Nair. “They include Conner Ives who had learned about her through his mother, who had once bought a hairband like Carolyn’s. You realise how many people have taken small elements of her like that.”