Why you can't "get" the Carolyn Bessette look

Even though we really, really want to

Unfortunately, you can’t simply slip into a black turtleneck, black pair of flared bootcut trousers, a pair of loafers and a Prada bag and call it a day, “I’m channelling Carolyn Bessette-Kennedy”. It doesn’t work like that, as much as we’d all like to. Carolyn was striking not because of her minimalistic outfits but because she was herself. Yes, she favoured black. Yes, she gravitated toward neutrals. But that was never the point. What made her unforgettable was how she inhabited those choices, the self-possession, the refusal to perform. The clothes were an extension of her, not a shortcut to her myth.

I, like many others, have always looked up to her when it comes to style because she’s the ultimate cool woman. And as Love Story premiered last week, photos, videos and articles about JFK Jr. and Carolyn surfaced and resurfaced in full force. My TikTok is now filled with girls showing how to “get the CBK look”. The “look” being a minimal outfit with clothes almost every person can find in their wardrobe. Girls will put jeans, black knit and black boots; white button up with black skirt; beige skirt, black turtleneck.. it goes on. They show the polished, digestible version, the part of her style that can be itemised and linked.

don’t even need to make a collage, i’m sure you’ve already seen it all

But she also wore things like that:

Substack is filled with thousands and thousand of articles with lists of things to buy but not enough of the reality of it all. Shopping lists disguised as inspiration. The narrative is transactional: buy this, wear that and the identity will follow. But the reality of developing personal style, real style, is far less convenient. It takes a lot of time and effort to find it, to find yourself. There’s a quote I really love:

In order to be yourself, you have to have a self first.

It takes patience. It takes embarrassment. It is an unglamorous, deeply personal discovery. You have to wear the questionable (ugly) hat for months and genuinely think you’re cool. You have to go through piles of clothes, most of which ugly (especially if you’re vintage shopping), in order to find that one perfect piece. It’s about trying different textures, shapes, styles. You have to know why you’ve bought something and feel absolutely incredible wearing it. Feeling like the coolest person to ever walk the earth. It’s about understanding why something belongs in your wardrobe, not because someone told you, but because something in it resonates with who you are and, most importantly, who you want to be.

Everyone falls head over heels for Zendaya’s red carpet style. That’s because she appreciates, lives and breathes, each and every look she wears. Dressing up and going about in the world should be fun, it has to be theatrical, but not performative, you have to have references. Real references. Not, “I chose this black t-shirt because of CBK”, something more meaningful.

The same principle applies to runway shows. Beauty alone no longer suffices. A garment can be exquisitely made, objectively beautiful, but if it lacks depth, if it lacks narrative or intent, it evaporates the moment it leaves the runway.

beauty by andy warhol

The irony of modern style culture is that while we claim to crave individuality, we continuously chase formulas. “Get the look,” “build the wardrobe,” “shop the aesthetic.” We are encouraged to replicate rather than explore. But style has always been, at its core, a form of self-knowledge, a reflection of how well you understand yourself. This is ultimately why the idea of “getting the look” so often falls flat. You can’t link that. You can’t replicate it from a single photograph of a woman in a black slip dress walking through Tribeca. You have to earn it - experiment, fail, succeed, cringe, revise and begin again.

Someone once said that true personal style means being able to remove the face from a photograph and still know exactly who the person is. Alexa Chung, for example, has referenced Jane Birkin as her style icon for years, yet she always looks like herself. You can easily spot the similarities - the basket bag, the undone hair, the ease but they’re not replicas, they’re translations. She filters the inspiration through her own proportions, her own perspective. The result is something informed by Birkin, but unmistakably Alexa.

The most memorable style has never been about perfection or replication. It’s about presence. About inhabiting clothes with intention and letting references inform rather than define you. Because in the end, the goal isn’t to look like someone else, it’s to be so fully yourself that no explanation is needed.

Thank you for reading all the way to the bottom! Hope you enjoyed and yes, Love Story is very good.

Anna x