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. The boom of street-style shots of men in Milan and Florence have since influenced menswear just as much as the runways of Paris and London. With nothing more at their disposal than great clothes, superb taste and enviable self-assurance, men such as Messrs Lino Ieluzzi, Luca Rubinacci and Simone Righi have become menswear 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? That Italian sensibility is so important, in fact, that we’ve even written an entire guide on how to be more Italian yourself (spoiler: it involves ironing your underwear).

But how does one dress like an Italian? To add a touch of Italian swagger to one’s personal style requires a brief study of both the small things (such as sleeve lengths) 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.

There are many paradoxes in Italian men’s style. One is the idea that putting on a suit is always inspired by the wish to look smart. Try replacing the word “smart” with the word “good”, because formality isn’t the priority here. This is why cotton and linen jackets, which are seldom seen in traditional British tailoring, are such a major part of Italian style (and of course the climate plays a part). None of these guys shown here wear clothes that fall into the category of conservative business dress, but all of them look undeniably cool. Men fixated on looking “sharp” will be appalled by the wrinkles that are an integral part of wearing cotton and linen, but those wrinkles help to make an attractively relaxed impression on the people around you. Learn to embrace them.

A man needn’t have a huge wardrobe; he just needs the right clothes. And one of the reasons for this is that it takes time to get clothes just right, as the two gentlemen in this photograph amply demonstrate. It’s highly unlikely that when they first tried on their trousers they were the perfect length. They’ve spent time having them tailored so that they sit at exactly the right height in relation to the shoes – the trousers on the right just kiss the wearer’s chestnut-coloured double monks, while the chalk-stripe trousers on the left exhibit the perfect “shivering break”, when the hem meets the shoes’ vamps without rumpling – and well-judged chunky turn-ups. The lesson here is to find a skilled alterations tailor, build a relationship with him or her and assiduously have your clothes altered to fit.

It’s frequently noted fact that the late Mr Gianni Agnelli, one of the most stylish Italians of the 20th century (a competitive field), wore his watch over his shirt cuff. But that shouldn’t lead lesser mortals to conclude this is a quirk worth emulating. Much more interesting is the knack Italian men have for sizing their watch bracelets and straps so that they grip the exact spot where the wrist meets the hand. This has the effect of keeping the watch in place, rather than allowing it to spin around the wrist, while fixing it sufficiently far enough down the arm as to be permanently visible (which was presumably the motivation behind Mr Agnelli’s affectation). The ideal timepiece for such horological flourishes is a vintage Rolex sports watch, perhaps a Pepsi Bezel GMT, an early Submariner, an Explorer or – for the very well heeled – an early Daytona.

The Italian stylist Mr Robert Rabensteiner sets his own dress code, which makes his decision to wear a classic, navy-blue, double-breasted suit rather interesting. However, rather than looking as if he’s wearing a stiff, corporate uniform, Mr Rabensteiner crucially alters the impression he makes with a few key tweaks. The first comes in the form of the soft and perfectly fitted shoulders, the second is the absence of a tie and the third is the way that he’s popped his collar. The jacket’s fit suggests the suit may be bespoke, in which case we applaud Mr Rabensteiner’s decision to go for hip pockets without flaps as these give a sleeker look. The navy jacket is a key element in the Italian man’s wardrobe.

Italians are generally too smart for full workwear looks, but have a knack of introducing elements of it into an outfit in a way that looks entirely coherent. In this shot, fashion consultant Mr Alessandro Squarzi effortlessly combines crisp white chinos, a gingham button-down shirt, a Wabash fabric waistcoat and a vintage US Army overshirt. It’s an outfit further distinguished by the crocodile (or is it alligator?) belt buckle, but the lesson here is how Mr Squarzi uses well-fitting vintage pieces to give his outfit visual depth. The effect is interesting without being attention-seeking and one of the reasons for this is the harmonious combination of the colours – in particular the mix of olive green and white.

Because Italian style is so distinctive, it’s tempting to assume that Italian men wear loud clothes. In fact, the best of them do the exact opposite, as these gentlemen prove. Far from employing eye-catching, neo-dandy flourishes such as gaudy bow ties or boldly coloured chinos, they are dressed in subdued shades of sand and stone, with pale-blue shirts and grey ties. Despite the ties and the tailoring, the impression made is a casual one thanks to the bare ankles (a tan helps here), the cotton cargo pants and the brown shoes. Slightly more casual than what you’d expect to wear to, say, a lawyer’s office, this kind of outfit is perfect for a cutting a sharp figure at a summer wedding.

“Deconstructed” is another one of those lazily used terms that can mean almost anything, whether it’s Michelin-star food that’s been dissected beyond recognition, or a coffee with its component parts split into separate receptacles. When it comes to tailoring, however, it’s a concept worth taking note of. It’s when a jacket is made without any unnecessary padding or lining, which means it’s not only lightweight, but cooler and softer than traditional suiting. Naturally, the Italians invented this virtuous method of construction and a good deal of credit for its popularity has to go to Boglioli, whose featherweight jackets are a must to survive the oven-like summer heat of Milan and Rome. Don one of these and you’re well on your way to capturing the insouciant spirit of sprezzatura.

Italy is rightly famed for its craft skills when it comes to apparel manufacture, and alongside leather goods, it has always excelled in the production of eyewear. This makes total sense, seeing as some of the world’s most renowned optical brands, such as Persol – favoured by Hollywood legend and style icon Mr Steve McQueen – hail from the country. This look is all about oversized 1970s frames, and no one knows more about louche maximalism than the Italians. Whether it’s a pair of gradient aviators or metal D-frames, a pair of bold shades is an essential ingredient.

In a similar fashion to the way they tie their scarves, Italians are masters of styling pocket squares in an elegantly undone fashion. The key to mastering the skill is to avoid obsessively neat or precise folding. It’s all about making it look natural, as illustrated above. This can be achieved by the simple action of inverting a puff fold, which happens to be one of the easiest folds to master. With the square laid flat, pick it up by pinching the centre, use your thumb and index finger to form a ring and pull it through, then finish by folding the pointed edges over each other. Now casually stuff it in your breast pocket with the points facing upwards and you’re good to go.