I don’t know what’s happening, but the level of sloppiness in what some guys are wearing is simply getting out of hand.  Loud colors, ill-fitting clothes, sunglasses at night– it’s not stylish, it’s sloppy.

If you want to look as if you don’t care, that’s fine, but please do it with style.

Or more specifically, with sprezzatura, the Italian term for “artful dishevelment” as I call it (it’s not a literal translation).  You may do it already without knowing: sprezzatura is dressing like you don’t care, taking a nonchalant attitude with your appearance—when in fact you do take time and effort to create your look. 

The trick to pulling it off is subtlety, confidence and an otherwise impeccable outfit.  Let’s examine probably the greatest example of sprezzatura, Mr. Gianni Agnelli. Look at this picture of Mr. Agnelli in deep thought.  What is peculiar about his outfit?

Look carefully…do you notice his wrist?  It’s more apparent in this photo because your eye is naturally drawn to that area, but it has to do with his wristwatch.  Mr. Agnelli would often wear his watch outside his shirt cuff but under his jacket. 

The trick to successful artful dishevelment is twofold: subtlety and great sartorial know-how.  Imagine meeting Mr. Agnelli.  Would you even notice the watch?  Only if you looked carefully.  And that’s the point: the fashion quirk is subtle and understated.  If Mr. Agnelli didn’t comb his hair or if he wore an extremely wrinkled dress shirt, the dishevelment would no longer be “artful” but simply sloppy.

But even more important is that Mr. Agnelli’s suit is impeccably well cut.  He has great sartorial knowledge and flawless taste—and it shows.  If he wore an ill-fitting suit and a strange shirt/tie combo, people would consider him sloppily dressed.  But because his suit fits him perfectly, he still looks sharp.  That’s the fine line between artful dishevelement and simple sloppiness.

First of all, notice the loosened tie.  Many men do this out of comfort, but they don’t consider how sloppy it can look.  But when Mr. Bastian does it, it looks stylish. Also, notice his jacket cuff.  See the two buttons unbuttoned?  Finally, look his unbuttoned jacket.  There’s a style “rule” that suit buttons should always be fastened whenever you’re not sitting.  Mr. Bastian looks like he’s giving that rule the proverbial middle finger.  You know he knows that rule, but he doesn’t care.  Sprezzatura is as much about confidence and attitude as anything.

I’ll share one more sprezzatura example: Stefano Tonchi.

Take a look at two things: (1) the single button fastened on the jacket, and (2) the part of the collar outside the jacket lapel, but not in a Tony Montana kind of way.  That’s his subtle quirk; what’s yours?

Notice in all three cases the lack of obnoxious wear: well cut suits with no loud colors, and confidence without cockiness.  That’s what separates these three from the average guy at a club on a Friday night.

It’s hard to look like you don’t care when you do.  When it’s done wrong, you have stereotypical “Los Angeles fashion”; when it’s done right, you have Mr. Agnelli, Mr. Bastian, and Mr. Tonchi.  It’s the difference between sloppily bad and eternally cool. 

Style tip? Steven Alan produces a great line of shirts that come wrinkled (if you’ve never seen a display of his clothes, they even hang on the rack at stores wrinkled and creased).  These shirts are a great place to start if you’re trying to get a feel for this sprezzatura.  But the bottom line is that true sprezzatura can’t be done for you and no one can tell you how to pull it off; it’s about feel.  And it varies from outfit to outfit; a wrinkled shirt in one outfit won’t necessarily look good in a different outfit.