'Timeless' is a word we use a lot in the world of fashion, but it really does sum up the late Carolyn Bessette-Kennedy's style best. The proof? Every single item of clothing I've come across while researching this piece would look just as good today as it did when she was thrust into the spotlight in the 1990s.
A true pioneer of the capsule wardrobe, Carolyn knew what worked for her and stuck with it. Anyone who was there at the time will no doubt remember her as the style icon she was. From the slinky Narciso Rodriguez wedding dress she chose when marrying John F. Kennedy Jr., to the oval sunglasses she so often wore when out and about in New York, she had her own anti-trend style that was the epitome of effortlessly chic.
The new Ryan Murphy show Love Story: John F. Kennedy Jr. & Carolyn Bessette tells the story of her romance, but also her career at Calvin Klein, where she rose from sales assistant to director of publicity. The brand no doubt encouraged her love of minimalism - her wardrobe was always pared-back with no logos, and few prints or bright colours. She wore little or no jewellery, and she stuck to trusted labels like Prada and Yohji Yamamoto.
Sarah Pidgeon (pictured, top, filming scenes for the show) portrays Carolyn Bessette-Kennedy in the series, and not only is it beautiful to watch her whirlwind romance with JFK Jr. (played by Paul Anthony Kelly), but her outfits have been stunningly accurate.
Feeling nostalgic for the 90s? I've been shopping to find the best ways to recreate the look. Minimalism is back to the max at the moment, thanks to high-end brands like Toteme and The Row, but the high street has got some amazing options, too.
Pencil skirt & knee-high boots
This has to be one of Carolyn's most famous outfits, and rightly so. It exudes elegance, and yet it's all so simple. A V-neck sweatshirt like this one (which just so happens to be by Calvin Klein) will go a long way in your wardrobe. When you're not wearing it with a pencil skirt, jeans and loafers will complement this perfectly.
This full outfit was Prada, and it's one that has been much-copied in the years since. This sophisticated skirt will do the trick, and there's even a matching blazer for a big day in the boardroom.
There's a reason knee-high boots never go out of style. These are an investment buy from one of the best British clothing brands, and I guarantee the leather will only get better with age. They're also available in black, chocolate brown or cherry, too.
Signature accessories
Carolyn famously bought her signature headbands from C.O. Bigelow, a pharmacy in New York, proving that this is one accessory that you don't need to fork out a fortune on. For a little over £7, this one has non-slip teeth and a flexible fit, so you won't be counting down the minutes until you can take it off. We all know there's nothing worse.
I just added these leather loafers to my own shoe collection after falling in love with the suede version last year. They're the best on the high street right now if you ask me, and they're available in half sizes too, so you can find the perfect fit.
There might have been no social media in the 90s, but Carolyn was still one of the most photographed women in the world at the time, so her oval sunglasses soon became a non-negotiable. Supposedly, she bought hers from New York-based label Selima Optique, but these Le Specs sunnies are the best match I've seen.
Jeans & boots
Mastering a capsule wardrobe means getting the basics right, and this waffle-textured top is a really elevated alternative to your usual white T-shirt. It's even called the "Bessette".
We told you she was a style icon, and these jeans are also named after CBK. She regularly wore bootcut denim, and these fall at just the right length to show off your shoes. They're 100% cotton, and are available in sizes 24 to 32.
Bootcut denim demands a good pair of boots to team with them, and you'll want to wear these chunky-heeled beauties all the time. I've heard good things about Next's Forever Comfort range.
The perfect winter coat
Her Prada camel coat is probably one of Carolyn's most-worn items. With a button-down front and pockets, this military-inspired option from ME+EM is hands-down the best lookalike I've come across. Invest now, and you'll be wearing it for decades.
Reportedly, CBK's Levi's of choice were the 517s, which were originally a mens pair. This bootcut is the closest you can get nowadays. The placement of the back pockets is super flattering, and so is the high waist fit and gently flared shape.
Carolyn was frequently pictured carrying the Prada Spazzolato tote bag, with its smooth leather finish and unfussy design. This pre-loved Prada is not to be missed. It's pricey, but you'll never need to buy another bag ever again.
An unexpected print
You rarely saw Carolyn wearing prints (although I'm pleased to note there was one leopard print coat in there!), so when she made an exception to this rule, it was for something really good. Her camellia print dress was by none other than Chanel, and this pretty pink option from Rixo is the 2026 way to get the look.
CBK's shoes were Manolo Blahnik, but now that slingbacks are well and truly... well back, you can find amazing matches on the high street, like these £60 heels from Mango.
I never would have thought to pair of pink floral dress with a black shoulder bag, but it actually works so well. This structured option is the ideal size for all your essentials.
A monomochrome masterclass
Satin skirts and dresses were a key component of CBK's closet, and this midi-length option from Zara will go a long way in your wardrobe. Wear it with a crisp white shirt, or layer it up with a chunky jumper and ankle boots while it's still chilly.
With Nothing Underneath are the best when it comes to shirts - I should know, I think I had five styles in my wardrobe at the last count! This classic white option will take you from denim to dinner party - how many other pieces can you say that about?
Carolyn rarely wore jewellery, and when she did, it was super subtle. Her engagement ring was a sapphire and diamond band that was said to be inspired by her late mother-in-law's "swimming ring", while her wedding ring was a simple gold band. It's proof that sometimes less is much, much more.
Love Story: John F. Kennedy Jr. & Carolyn Bessette is available in the UK on Disney+. New episodes are released weekly on Fridays.
