‘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.
Pencil skirt & knee-high boots
(Image credit: Getty Images)
Calvin Klein
V-Neck Terry Relaxed Sweatshirt
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.
Boden
Skye Smart Knee Boots
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
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Auroriel
Tortoiseshell Hairband No Slipping Comfortable Headband
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.
Le Specs
Outta Love 51mm Oval Sunglasses
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
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With Nothing Underneath
Bessette Top: Waffle Jersey in Off-White
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”.
Alex Mill
Bessette Mid Rise Bootcut Jean
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.
Next
Black Patent Forever Comfort® Square Toe Block Heel Ankle Boots
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
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ME+EM
Fitted Military 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.
Levi
Wedgie Bootcut Jeans
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.
RESELFRIDGES
Pre-Loved Prada Soft Triple Pocket Leather Tote Bag
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
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Rixo
Clarice Chiffon Midi Dress in Kimmie Floral Pink
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.
Mango
Pointed-Toe Leather Heeled Shoes
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.
ASOS Design
Structured Shoulder Bag
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
(Image credit: Getty Images)
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
The Boyfriend Exaggerated Cuff: Fine Poplin, White
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?
Monica Vinader
Gold Vermeil Siren Hammered Ring
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.
