
Dressing well can feel unnatural at first. As you put on clothes you’re not used to wearing, you might feel a bit out of a place. Like a poser, even. You want to look natural in what you wear, but it doesn’t seem to come, well, naturally.
People talk about sprezzatura, that Italian buzzword which conveys a sense of effortless elegance. But actually, what it really conveys is the appearance of effortless elegance. In practice, it often means taking 30 minutes to adjust your pocket square so it looks like you slipped it into your jacket without a second thought.
In other words, it’s rather vain. And certainly not “natural”.
So what’s the real key to looking natural in what you wear? To ensuring your clothes feel like an extension of yourself, and not just a costume you put on in the morning?
I’ve been thinking about this a lot the past few weeks, as I realized that much of the stuff that would have once felt odd on me — a summer jacket, an ascot, etc — now feels like an afterthought. As in, sometimes I literally forget I’m even wearing it. What I realized is that actually, feeling natural in your clothes is way easier than most people think.
So what’s the secret? As it turns out, it’s no different from anything else you do…



