The Coolest Girl In Town

Let me introduce you to a new idea: Making your most powerful outfit not look powerful at all. As if you got dressed without thinking too hard, almost like an accident. 

Carolyn Bessette has mastered this illusion. A white button down, a black skirt, a slip dress, and undone side parted hair. Nothing about it felt loud, yet the images of her running away from paps in New York city have become some of the most referenced pictures till date. Her outfits never tried to impress vogue’s critiques, but that's exactly why they were. 

Let me be honest with you, the illusion of looking unbothered is never an accident, it’s careful consistency. Build your wardrobe around a narrow set of choices: sharp outerwear, personal stacks (I am done seeing Rolex watches, a tennis bracelet and a Cartier), almost undone lipstick, completely undone hair, and a lot of Calvin Klein dresses. And it’s okay to repeat silhouettes constantly, repetition creates clarity. But also the role of mystery is very important, a part of what made Carolyn’s style so compelling was the absence, the scarcity really really matters, so don't force yourself to post a picture of every single outfit, when the attention needs to be on you, trust me, it will, and when it does it will be the right kind of attention, the kind that you deserve. 

Why can’t this exist today? 

Let me tell you one thing, fashion culture now operates on a different set of rules and hopefully no regulations. In today’s world, fashion is documented constantly, we appreciate visibility, constant reinvention and that sense of instantness more than anything, everything rises and falls within a week. Hence, effortless dressing struggles in this environment because it thrives on repetition and consistency. Like, when was the last time you were happy repeating an outfit? 

Effortlessness needs the exact opposite, it requires patience and willingness to wear the same coat ten times without whining about it to an audience. Know that in a world of performance, indifference is hard to maintain. 

And, I know what people are getting wrong here. I am not asking ya’ll to copy her style, copy her mindset of not missing the point. That difference is subtle but powerful. She communicates something so much deeper: indifference to trends, confidence in repeating, and limited visibility. 

The strength in Carolyn is the refusal to perform, the rarest aesthetic of all.