Cool vs. Effortless

It’s Personal Style day on Man Repeller — feast your eyes on this.


I have always wanted to look cool. To be the kind of girl who not just makes you think you can do that too but forces you to want to try it. I want to exude that sense of: she could be wearing a potato sack and still look great. Maybe in fact, in that last approximation, I am wearing a potato sack.

Fundamentally, though, I understand that I’m not cool.

You can’t fake cool — cool is inherent and you either are it or you’re not. This means nothing about style other than, I suppose, that to be cool immediately vaccinates a woman (or man) against bad style. Think Johnny Depp or Daria Werbowy or Erin Wasson. With Depp’s hair so dirty it is almost dreadlocked, or Werbowy’s insouciant nose ring and dirty white tank tops, or Wasson’s ripped shorts and desert boots, these icons-in-their-own-right emit a sense of style that we love not because of the clothes but because we’re attracted to the swagger.

It is effortless by definition, though interesting to note is the fact that “effortlessness” as a style movement can be faked. And well, at that. If it’s true that good artists copy and great artists steal, then when it comes to fashion, effortless dressing is at the crux of this saying. Designers like Phoebe Philo or Clare Waight-Keller — with their clean lines and silhouettes that whisper, not yell, with great aplomb — have mandated so.

This is arguably what has incited the viral concept that is “normcore,” but something people fail to recognize quite frequently with normcore is that looking like you didn’t try — pairing flip flops with jeans and a silk blouse, or a dress with dirty tennis shoes — doesn’t necessarily mean you’re in style. You might be on trend, but when considering the umbrella of style, which does not shield the pour of trendiness, there is another variable at play and that is impressiveness.

I have deduced, based on conversations with friends about the garments they say they’ll never tire of wearing, and images of Anna Wintour, standing relentlessly and with poise in her Manolo Blahnik sandal mules, that good style doesn’t aim to impress anyone but the self.

It’s a private conversation between the wearer and the clothes. Wintour, along with any of the aforementioned friends, choose the items that they choose to wear over and over again, not taking into account a third party opinion that might role its eyes at the redundancy, because the items, whatever they are, suit the wearers.

They make them feel like the realistically best or most accurate versions of themselves.

These “versions” may appear polished because that might be someone’s sense of effortless. They might also not, but at the respective core here is either the illusion of effortlessness or an accurate portrayal of it. And no matter how you slice that, a new progeny is born and that is authenticity.

Now to be able to fake that seems pretty damn cool.

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