Sprezzatura - achieving style without appearing to try too hard

I've had plenty to say before about trying too hard with your style. It rarely works, because it looks contrived and self-conscious. I'd heard the word sprezzatura before, but now see that it defines precisely what I've been trying to describe in previous posts on this blog. This was brought home to me by Mr Porter's report on this expressive Italian word in their Journal. Here is what Wikipedia says,

Sprezzatura (Italian pronunciation: [sprettsaˈtura]) is an Italian word originating from Baldassare Castiglione's The Book of the Courtier, where it is defined by the author as "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". It is the ability of the courtier to display "an easy facility in accomplishing difficult actions which hides the conscious effort that went into them". Sprezzatura has also been described "as a form of defensive irony: the ability to disguise what one really desires, feels, thinks, and means or intends behind a mask of apparent reticence and nonchalance".

The word has entered the English language; the Oxford English Dictionary defines it as 'studied carelessness'.

So, the look may involve purposeful (or, if you're really a natural, unintentional) imperfection in dress; undone buttons, no perfection or symmetry - maybe even slight shabbiness. However, these things need to be done very carefully if they are not to look too contrived. Ties at half mast and brogues worn without socks will fail as it is trying too hard. 

Here are a few examples; many of which I've used before. These men are all dressed very stylishly, but none is immaculate. Do any of these ideas work for you?

Let's try a little sprezzatura this summer.

Boglioli

The Sartorialist

The Sartorialist

The Sartorialist

The Sartorialist

The Sartorialist