When it comes to clothes, “made in Italy” is synonymous with the tangible virtues of quality, craftsmanship and design. It’s far harder, however, to put one’s finger on what it is exactly about the way the most stylish of Italian men themselves dress that sets them apart. Italian men’s style is instantly recognisable, but what are the sartorial quirks that take their outfits to the next level? This very question was part of what inspired Mr Scott Schuman to set up The Sartorialist way back in 2005 – he wanted to record the way that men in Italy’s big cities dress in order to decode their tricks and understand how they do it.

All these years later and the world of men’s style has changed immeasurably. And yet, with nothing more at their disposal than great clothes, superb taste and enviable self-assurance, men spotted on the streets of Italy are still style superstars. But what is it about the way they update classic outfits that works so well? How do they achieve that distinctly Italian look, at once careless and artfully put together?

And how does one dress like an Italian when one is decidedly not? To add a touch of sprezzatura to one’s personal style requires a brief study of both the small things (accessories) and the big things (fabric and colour choices) that Italian men deploy to achieve their winning looks. Because, wherever a man lives, there will be something he can learn from the world’s most stylish nation.

The concept of stealth wealth has taken over the neutrals conversation of late – and we’re certainly not against choosing ultra-luxurious, yet incredibly simple clothing as a style choice. But neutrals don’t have to be perfectly pressed, cut slim to the body, or on the camel side of the spectrum in order to be elegant and charming.

See this gentleman’s cunning example for inspiration. Each item has a louche, devil-may-care appeal, from the voluminous white trousers to the khaki shirt and fishing jacket. He is toeing the messiness line, but manages to keep on the right side of it by assembling an intentional outfit of clean, pressed pieces. Elegant amber sunglasses and a clean white tote indicate that choices were made here, which is the deciding factor between sloppy and suave.

“Tonal Dressing” is fashion speak for wearing an outfit consisting entirely of different tone of the same colour. In this case, blue is used to great effect on top, on bottom, and as outerwear. This is also a good example of how to wear top-to-toe denim without seeming like you’re moments away from hopping on a horse. The secret is choosing a chore coat in a softer fabric and accessories (like these 1950s inspired frames) that would be out of place on a ranch.

This chore coat deserves another look. It’s a little hard to tell from this picture, but it seems to be crafted from some sort of gingham or seersucker. The fabric, plus the white buttons, plus the double-breasted silhouette add an old-school artisanal luxe appeal to the double denim below.

The tyranny of crewnecks and rollnecks is over, long live the knitted polo shirt. This 1950s-style piece is versatile and adds texture, making it much more visually interesting than a T-shirt or classic button down. They may seem more challenging to style, if only because we’re not used to them. But this gentleman is showing us that we need not overthink it.

He’s swapped out an Oxford for a honey-coloured open-knit to wear under his very wide-peak-lapelled linen sport coat in an olive green. The trousers appear to be a classic navy wool blend. Altogether, the colour scheme is simple and stylish. And the mix of textures is inspired.

Perhaps the very essence of Italian dressing is sprezzatura – the art of effortless. Wearing a suit effortlessly often feels like a contradiction in terms. After all, isn’t a suit the definition of effort? Here, however, we see that tailoring can be understated and cool, soft and unstudied.

The secret lies in classic Italian tailoring, which is traditionally less structured than English tailoring and often unlined (this jacket, for example, is unlined). Softer padding at the shoulders, and some clever pocket placement, make this a suit that you could wear to a lunch or on a date. Wearing an Oxford instead of a dress shirt also helps to make this outfit more relaxed. He looks as though throwing this on was as easy as plucking a T-shirt and jeans from his dresser. And, of course, that’s the beauty of a beautiful suit – it can actually be the simplest, most effortless item in your wardrobe.

It can be tempting to add, inexorably, to your wardrobe, following the trends, buying the new now next, until you cannot fit even one more hanger into your closet. But, we – and the well-dressed Italians – believe in investing in timeless pieces that can be accessorised according to whim and will never go out of style.

See here, a chambray shirt is worn beneath a slightly shrunken, unlined, double-breasted navy blazer. There is a silk handkerchief both tucked into the breast pocket and tied, insouciantly, around the neck. We spotted dozens of neckerchiefs at Pitti Uomo this year, and this is a fabulous example of how one might use a silk scarf to bring a little playfulness to such a classic jacket. Worn a different way (perhaps as part of a suit), this blazer could be much dressier. If we’ve said it once, we’ll say it one thousand times, a navy blazer is the epitome of versatility.

Our senior fashion editor saw this picture and was blown away. At first, that may leave you scratching your head. It’s just a blue shirt, white trousers and a white tee, right? Well, yes, but this gentleman has added teeny tiny little details that bring this casual look to the next level. A beaded necklace, beaded bracelets, and tortoiseshell sunglasses signal a man who has taken some care to look so suave.

The fit of the shirt and trousers is also of note: loose and breezy, he’s managing to be rumpled and neat all at once. Not an easy feat, but made easier if you cuff your sleeves just so, and deploy accessories strategically.

What’s the expression? You must know the rules in order to break them. We all know that a properly tied tie involves a neat knot, and a narrow end that sits snugly behind the wide part. This hirsute signore has it all wrong, but it looks quite right, indeed.

It helps, of course, that the rest of the outfit is completely on point: a well-fitting blazer, a clean white shirt, a well-combed beard. The sum here is greater than the parts. And, frankly, we think the akimbo tie is sprezzatura incarnate – it makes the look. We’re not saying you should start haphazardly tying all ties (this is one trick to be deployed sparingly), but maybe you can give yourself a break once in a while from perfection.