The Problem With Turning Carolyn’s Timeless Style Into a Trend
Let me introduce you to Carolyn Bessette Kennedy: the woman who turned 90s minimalism into a blueprint that everyone is still trying (and failing) to recreate. With the release of “Love Story”, a biographical romance drama about Carolyn Bassette and John F Kennedy Jr, increasing numbers of people trying to recreate some of CBK’s most iconic looks have surged on the internet. Scroll for 5 minutes, and you will find it everywhere: “How to dress like CBK”, “the Calvin Klein Resurgence”, or “ CBK but modern”. Each video is filled with capsule wardrobe pieces; perfectly curated “effortless” outfits laid out with clinical precision. The go-to recipe: black coat, slip dress, sunglasses, and not a necklace in sight!
Except… we are all missing the point! Making the effortless effort sucks the thing that made CBK’s wardrobe so iconic out of it. What made Carolyn’s style so compelling wasn’t that it could be replicated but that it wasn’t trying to be. CBK was not dressing for an audience; the non-existent social media culture allowed for her to dress for comfort and simplicity without worrying about a stream of 22-year-olds trying to ‘discover their style’ based on her latest workout wardrobe. She was not building her wardrobe to be paused, dissected, and reassembled over and over for content; instead, the simplicity people are obsessing over today was not constructed to be seen as ‘aesthetically simple’. It just was. And that is exactly what gets lost. To replicate her look by today’s standard requires a lot of effort.
It requires sourcing the ‘vintage coat’, the perfectly cut trousers, and the exact shade of off-white. People are searching for formulaic answers, guides to follow, and in turn following tutorial after tutorial claiming how to ‘effortlessly’ dress like CBK. Ultimately, then, this overattention to detail turns something that once read as natural into something staged. We are, collectively, trying too hard to make something look like we are not trying at all. And in doing so, we have turned a style from something lived in into something performative.
Timelessness doesn’t work like this, so making ‘timeless chic’ a trend ultimately strips it of its authenticity. Instead, we are left with a stream of videos all claiming to be the cheat code for CBK, which will inevitably be lost after the next trending ‘timeless’ fashion icon to come in. Faking comfort and confidence cannot replace what made CBK’s wardrobe so iconic, no matter how stunning the outfit. So, if we are to learn anything about fashion from this iconic resurgence, let it be this: rather than focusing on buying a whole new wardrobe to fit the season’s style persona, let’s be inspired by CBK’s approach to fashion, not the fabric she wore. Wear what is comfortable, usable, and ultimately you.
That is truly timeless. Real ‘effortless’ will come from this. It doesn’t need a guide or 10,000 TikTok tutorials to tell you what fashion simplicity is. It doesn’t announce itself or ask to be noticed. Which is why trying to recreate it will always feel slightly off. Not because we are doing it wrong, but because it was never meant to be done at all. And that’s the point we keep missing.