And what you can learn from him.

My Encounter with the Best-Dressed Man in Italy

He isn’t a fashion model. He isn’t a style icon. He isn’t an influencer. I don’t even know his name.

He’s an old man who walked past me one evening in Bologna. Most people wouldn’t have noticed him. His style was understated and unaffected and even a bit louche. And he looked like he couldn’t care less about proportions, lapel widths and all the rules of #menswear. I should have stopped and bought him a coffee.

I was on a menswear pilgrimage in Italy when I had this brush with effortless style. They may not have made it to the World Cup, but Italia is the undisputed champion of men’s style.

I began my journey at Pitti Uomo in Florence, a twice annual menswear tradeshow that’s become the place to be for style lovers. Sure, there are the international brands you’ve heard of, and plenty you haven’t, but you’re just as likely to run into all the menswear writers, photographers and influencers you follow on Instagram. And then there are the Pitti Peacocks—a group of guys in outlandish outfits who stand around the main outdoor plaza hoping to be photographed. To what end, no one is sure. Except for these clowns, it’s mostly classic elegance on display. Superb hand tailored jackets. Sexy split toe derbies and Belgian loafers. Unlined silk twill ties that celebrate male sophistication. And plenty of guys dressed impeccably.

But sometimes doesn’t that seem a bit too polished? A shade too mannered? I’ll happily put up my hand and admit my own guilt here. There were moments at Pitti when I felt my clothes were wearing me, not the other way around. One day in particular when I got carried away with blue: blue shirt, tie, jacket and trousers. Thank God I don’t own blue suede shoes. And I suppose with all that fine menswear on display, it’s hard for anyone to really stand out. If I had seen just one or two of those guys on the street, I could have appreciated the tailoring of their jackets or the way they combined colours and textures. But amidst the crowd, subtlety is lost.

Then I was off to Milan, the home of the world’s best dressed businessmen. Serious and respectable without looking drab. It’s amazing what a bit of colour and a textured grenadine tie can do to an otherwise traditional outfit. And some Italian dash. Literally. A common sight in Milan is a man in a slim blue suit with soft yet slightly shaped shoulders, an ice blue shirt, dark tie and tassel loafers, whizzing past you on a moped.

He was expressing that most Italian of style approaches, a word I try to avoid using because it is so overused and abused: sprezzatura.

I also traveled south to Naples, the home of Italian hand tailoring. No other city has such a concentration of tailors, trouser- and shirtmakers. And it shows. A lot of men, not just a select few, wear tailored jackets every day. By far the most common outfit I saw was a blue sport jacket and cream trousers with an open collar blue shirt—showing off a hell of a lot of heavage—and brown driving moccasins. Pretty much what I was wearing, (minus the heavage). The men looked damn rakish but I had to admit there was a sameness that felt less like personal expression and more like social conformity.

And finally, Bologna. A quieter city, somewhat off the beaten track—tourist havens Venice and Florence get most of the attention—and certainly not a pretender to a style throne. Bologna has a lot less self-conscious dress on display. Instead, I got to see how most urban Italian men dress. Lots of athleisure, like here in Canada. But Bologna is also home to a small number of exceptional menswear craftspeople, so classic style has a presence. And thus one evening, while walking off a particularly fantastic and filling dinner of tagliatelle alla bolognese, the old man walked past me.

He was in his early 70s, shorter than I am, maybe 5’6”. A little on the heavy side. And his outfit was all wrong. The jacket of his off-white linen suit was a shade darker than his trousers. The shoulders hung slightly over his arms. The trousers were baggy. The collar on his white shirt didn’t stand perfectly under his jacket but sagged a bit to one side. His panama hat was banged up and misshapen.

But none of it looked shabby or cheap or careless. In fact, it looked natural. Effortless. Elegant. Because all of it was lived in. Worn for years. And worn well. Epitomised by his cream canvas shoes, which were neither pristine and glowing nor scuffed and dirty.

The old man could have stepped out of those English costume dramas Netflix suggests after you’ve watched Downton Abbey. Yet he also looked thoroughly contemporary because he wasn’t wearing his clothes like a costume. In fact, he looked like he truly didn’t give a shit what I or anyone thought.

He was expressing that most Italian of style approaches, a word I try to avoid using because it is so overused and abused: sprezzatura. This is often translated as “intentional nonchalance.” It’s expressed on Instagram by leaving buttons undone on jacket cuffs or with unbuckled double monk shoes. But that is not true sprezzatura. What some older Italians know is that clothes need to be worn and worn for years and years until they, and you, earn nonchalance. Until you just don’t think about it any more. You may notice, as you walk out the door, that one of your buttons is undone. But it’s been that way for so long, and not intentionally, that maybe you do it up. Or maybe you don’t. It doesn’t matter.

After weeks amongst some of the best dressed guys I know, seeing that old man in Bologna reset my internal style clock. Start with well made clothes that fit. Neither too in, nor out of fashion. Items that complement each other. Then wear them. For a long time. Season after season, year after year. Until they develop their own patina, slightly worn edges and relaxed seams. And naturally, over time, you will stop fretting and worrying about how you look. And then, maybe, hopefully, you’ll inspire some random guy who’s too shy to stop and buy you a coffee.