Sprezzatura takes time

The current menswear obsession of not looking obsessed with our clothes – sprezzatura – is not a new thing. The attempt to be intentionally nonchalant has been with us for decades, as this 1940 Stetson ad proves:

Seventy-five years ago, as the 1930s and the “golden age of menswear” were coming to an end, guys were already concerned with “carefully studied casualness,” looking lived in and laid back without looking like they tried. Interesting too that it’s called a “trend,” as it is now. And to be honest, I understand the sprezzatura motivation. Dressing well can sometimes look stiff and formal, especially today in our very, very casual world. Equally important is that you want to look like you are wearing your clothes, not the other way around. And so buttons are left undone, shoe straps unbuckled, hats bent out of shape. All to show personality and uniqueness. But to do this intentionally is to betray, in my opinion, the goal you are seeking. You cannot be at once aware and blissfully unaware of what you are wearing.

On the other hand, have a look at one of my style icons Luciano Barbera:

There’s a lot of sprezzatura going on here, from the jacket to the tie to the hat. But here’s the thing: Mr. Barbera has lived in those clothes for years, if not decades. They have earned their wrinkles and deep dents. I saw many hats like this when I was recently in Milan, hats that had long ago lost their original shape and were now truly lived in. All of them on older men. However, like the Stetson ad, most of us younger guys want authenticity now. We don’t want to wait for our clothes to look lived in, we want to look nonchalant already.

I have a number of hats. Most are brand new and so have that fresh-out-of-the-box look. My “oldest” new hat is just starting to look just a little worked in but it’s taken three years. It is only my fifty-year-old Biltmore that looks truly alive. The dent is deep and misshapen and the rabbit fur smoothed out and darked by years of grabbing the top of the hat. (I’m not responsible for all of this, of course, as I purchased the hat second-hand about a dozen years ago).

“Sprezzatura” is trying to not look too proper, too prim, which can come from clothes being too new and us being new to them. Your wardrobe may look and feel too fresh and too new now, but if you commit yourself to buying high quality items they will age beautifully, as G. Bruce Boyer often points out. In this way, you can look forward to growing older with your clothes. But it isn’t just your clothes that will benefit from the time spent developing this lived-in, rumpled look. The longer you live in your tailored clothes, the more comfortable you become with them. Personal idiosyncrasies will naturally develop over time. Eventually, your wardrobe will be a real extension of how you are and how you live. And isn’t the essence of true style comfort and confidence?

So by the time you’ve been wearing those shoes for ten years, that jacket for fifteen and that hat for twenty, you won’t even have to try to look nonchalant. It’ll be built in.