Our favourite outfits from the Florence menswear trade show.

The Pitti Uomo menswear fair, which takes place twice a year in Florence, is one of the biggest talking points in men’s fashion. This is partly because of the audacious peacockery the fair is famous for, which every season inspires a litany of think-pieces along the lines of “What a Pitti!” or “For Pitti’s Sake!”. Questionable puns and daft posturing aside, the streets of Firenze are still fat with sartorial promise. As well as the too-tight suits and straw boater hats you’ll see on chaps walking extra slowly past the street-style photographers, Pitti attracts plenty of men who can teach the rest of us a thing or two about dressing well. Below, we’ve picked out some of our favourite looks from Pitti, which demonstrate a different way to wear tailoring.

Most men who tried to wear a cap [out of shot], baggy trousers and sneakers would end up looking like overgrown children, but, with the addition of a double-breasted, brass-buttoned blazer, this chap has pulled off an outfit that we in the serious business of fashion journalism call “really, really good”. If there is a relaxed, easy way to wear tailoring, we doubt we have seen a more relaxed, easier way than this. Hats off to you, sir. Or hats on, as the case may be.

Here is a man with very few worries. He is holding some kind of diary or organiser, but it is empty. He is schedule free. In fact, that is not a diary, it is a sketch book or a pad with a few poems in it. That iPhone? It’s switched off. His day is clear. Whether this is true or not is irrelevant. He may well be an overworked accountant. But, boy, do his clothes make him look at ease. Yes, he’s wearing a nice, soft, beige bit of tailoring. But he’s paired it with a painterly striped top and a scarf. Bravo!

If you wanted to take things a little more seriously (but not too seriously, mind) you might slip on a shirt under your jacket. Not a smart Oxford, of course. A fun print shirt, naturally. It is summer, after all. Once we had finished admiring this gentleman’s shirt, we couldn’t help but notice the colour combination of his brown loafers, black trousers and red shopping bag. Accident or intentional?

Staying with the snazzy shirt theme, but dialling up the tailoring a little, we arrive at this guy. Look how pleased he is. And rightly so. He is happy because he has mastered the art of wearing a suit in the heat. Either that or his horse has just come in. Anyway. Loose fit? Check. Unstructured? Check. Fun pocket square? Yep. Sockless loafers? You get the idea. He’s got it all. The secret to this look? A good tailor and a fine eye for combinations.

This suit may well be the pinnacle of summer tailoring. It’s basically the same as his friend’s, above (perhaps they have the same tailor), but he has opted to have it made in the same colour as the sky. What could be more fitting for the season? He is also demonstrating how to execute a slightly smarter look with similar resources. However, instead of a print shirt, he has gone for a sophisticated yet casual half-placket number. It works so well we can even ignore the stain on his midriff.