Sprezzatura is an Italian word, the most accurate definition is “I-don’t-give-a-fuck-ness”. If you prefer to keep it G rated I guess you could define it as an effortless elegance, a nonchalance to one’s style, but that’s not quite right either. Because it’s not just effortless, although if you do it right that’s how it comes across. More than not caring, it’s a conscious rebellion, a defiance to society, a middle finger to all the rules.

The most famous example of this in the world of menswear is Gianni Agnelli, the famous “avvocato” who ran Fiat and exemplified Italian style in a way that no one else could ever do(There’s a documentary on him on HBO which I recommend). He was known for wearing the tail (skinny side of his tie) longer than the blade (front/wide part of the tie). This is something I do regularly for a couple of reasons.

First, it’s a salute for those who know. From the outside looking in it might seem silly, but if I ever see a man who is well dressed and keeps the tail end longer I just know he deeply understands and appreciates Italian style.
Second, it’s a statement for those who don’t. If I’m giving and receiving a “nod” from those who recognize this particular style choice, then what about the rest of the world – those who could see this as just a mistake. This is where the talent comes in, in making sure that your sprezzatura is done just right. I had an experience while I was living in New York that highlights this. I was riding on the A in a suit and a couple was looking at me, the young man leaned forward and said: “Hey the back of your tie is really long and outside of the loop”. Before I had the chance to thank him and explain that it was a choice the girl gently smacked his arm and said, “I think he knows, he doesn’t look like any of his outfit is on accident”. This put a huge smile on my face and we had a little conversation about it. The key to adding personality to your style is for the rest of your outfit to be so put together that it’s obvious (to most) that what you’re doing is intentional.

Doing it right

There are other ways to add sprezzatura to your outfit. Another of my favorites is leaving the buttons undone on a button-down collar. Wearing clip-on suspenders. Wearing sneakers or a t-shirt with a suit. Wearing your watch on the outside of your shirt sleeve(another Gianni Agnelli signature). If you think about it even the act of wearing a suit without a tie is a certain form of rebellion, it just happens to be one that is more widely accepted today. The key is to break a rule of traditional menswear in a way that looks intentional and stylish. As my mentor told me when I got my first suit in Italy, “choose your suit intentionally, put it on as though it costs millions, then wear it like a t-shirt”. It is important, as with every time you get dressed, to look and feel comfortable and confident. If you’re a cause for conversation, then you’re doing something right. Traditional menswear enthusiasts will scoff at clip-on suspenders, in fact, many did in this picture of Simone Righi, but it doesn’t change the fact that he looks stylish and put together. Say what you want, he looks good and doesn’t care what you think.

Doing it wrong

The fear in doing something like this lies in doing it wrong, and that’s a perfectly reasonable one to have. You don’t want to come off like a slob, and you also don’t want to come off as someone trying too hard, so how do you walk that fine line? What are the mistakes to avoid? First and foremost a big mistake is doing too much. In order for one choice to not look messy, the rest of you needs to be consistently well dressed. Second, don’t break a rule that you think looks bad – you maybe thinking, “well I think that stupid tie thing looks bad so what about that?” – if that’s the case then it should go without saying that you should not be doing that. For example, I don’t like, and so would never wear, an untucked shirt with a suit/jacket. It’s not that it’s a bad look, and if you don’t wear your jacket a lot I can understand why you might want to do this and avoid creases from tucking and untucking your shirt, but it’s not something that would come naturally to me.

So why am I telling you this? Well, many of you come to me for menswear advice and a few have even asked why I do certain things that seem off for such a menswear lover. The truth is that this goes into more than just menswear, it’s a way of life that extends into most aspects. If you’re going to break a rule or two, you have to make sure you balance it out with order. Think of a guy in a tuxedo with his bowtie undone. We all picture a James Bond type, and it works because the rest of the outfit is neat and proper. But what if the pants were too baggy, the jacket didn’t fit well, the shirt was an unflattering cheap rental, and the wearer was sweaty, dirty, and out of breath? Instead of the hero who is unwinding after an elegant night, the visual changes into a slob that doesn’t belong at a black-tie event. So right now that volt colored apparel and tie-dye hoodies are in trend, the way to pull them off in your casual attire is to use them as accents with otherwise understated styles. Think Will in The Fresh Prince, he wore his jacket inside out to reflect his personality, but with grey trousers and a shirt and tie to keep from looking like a total clown.

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At the end of the day, learn the rules so that you can bend them as you find ways to insert your personality into everything you do. From your outfits, to the way you decorate your home and office, and it’ll begin to affect the way you speak and act. As long as it’s authentic you won’t look like you’re trying too hard but also won’t look like a mistake, and that’s when it’ll look good.