Sprezza-what? Sprezzatura, What it is and why you should do it!

Good evening to you dapperites,

If you have been reading this blog then you know all about the rules of style and fashion. Well tonight I will help and encourage you to break them! I know what you’re thinking, Don’s been downing too much Canadian Club 100% Rye again (which is excellent by the way) and is losing his mind! But fear not my friends for you will be introduced to the term “sprezzatura”. So what exactly does this Italian word mean? It was first coined by 16th century Italian author Baldassare Castiglione and meant “”a certain nonchalance, so as to conceal all art and make whatever one does or says appear to be without effort and almost without any thought about it”. Today it simply means, “studied carelessness” or in a fashion sense, “perfectly disheveled” , “imperfectly perfect”.

I alluded to earlier about how this means breaking the rules. What did I mean by that? Well I will turn to an example from one of the all-time masters of sprezzatura, former Fiat chief Gianni Agnelli.

Notice in the first picture how that tie knot is a little twisted and has the skinny end longer than the other and protruding to the side? That’s sprezzatura. And in the second picture how his watch is worn over his shirt cuff? Sprezzatura again!

Here are my other favorite examples of sprezzatura collected from the interweb:

Tie hanging outside your sweater? Why not! Top button of shirt undone and tie hanging loose? I dare you tell me otherwise! Pocket square stuffed in there right before you walk out the door? Get the picture now?

The absolute key to pulling this off is….CONFIDENCE! If you are not confident while looking like this, people will notice and mention that something is off about your look. If you are confident, people will admire the sense of adventure in your style.

So, how can you get started doing this? Take baby steps, start by twisting that tie knot off to the side and have both ends flapping in the wind nearly side by side. Instead of neatly folding a pocket square, grab it, stuff it into your pocket and don’t bother caring what it looks like.

As you get more into it, start undoing your buttons on your shirt cuff for a more relaxed look outside the office and forget about neatly pressing your dress shirts all the time, embrace some wrinkles. Start wearing a thin patterned scarf with your suit! Is this button-down collar supposed to be buttoned down? Hell no!

Once you are completely confident, have fun, be creative, take some of my personal suggestions such as wearing a colorful d-ring belt like this with dressier pants. Got a crazy fun pair of socks? Use one as a pocket square. Get yourself a basic old bandanna, and tie it around your neck or wrist and stroll on out the door!

I’d like to end this post by showing off some of my personal case of sprezzatura syndrome:

did i forget to tuck my tie in my sweater? oops

did i forget to tuck my tie in my sweater? oops


button down collar, what button down collar? this pic is also a great example of mixing patterns, a wooly winter tartan and a summery paisley on a bright light blue background.


Yes this is a thin, silk-like pattered woman’s scarf. The pattern was too awesome to not buy it. # of f*cks given= 0

Just remember the key gentlemen…confidence. And on that note I bid you all a goodnight.

Keep it flashy, classy and dapper 😉

The Don



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