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Style Tips From Florence’s Best Dressed

With Pitti in full swing, here are the six things every peacock needs to know

  • Photograph by Guerreisms

When it comes to clothes, “Made in Italy” is synonymous with 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 dress that sets them apart. What are the sartorial quirks that result in Italian men being so heavily represented on street-style blogs? This very question was part of what inspired Mr Scott Schuman to set up The Sartorialist 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.

A decade later and the world of men’s style has changed immeasurably, with street-style shots of men in Milan and Florence as influential and eagerly anticipated as the latest looks from 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. 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?

Adding 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 make up their winning looks. Because wherever a man lives, there will be something he can learn from the world’s most stylish nation.


  • Photograph by Ms Elena Braghieri/Getty Images

There are many paradoxes in Italian 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 (of course the climate plays a part). In this shot, at least three of the men – and possibly all of them – are wearing cotton or linen jackets. None of these guys are wearing clothes that fall into the category of conservative business dress but all of them look 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.

  • Rubinacci Cutaway-Collar Linen Shirt

  • Massimo Alba Winch Bull Slim-Fit Stretch-Cotton Twill Trousers


  • Photograph by Mr Jacopo Raule/Getty Images

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 chalkstripe 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.

  • Caruso Blue Slim-Fit Mélange Wool Trousers

  • Berluti Leather Monk-Strap Shoes


  • Photograph by Mr Tommy Ton

The frequently noted fact that the late Mr Gianni Agnelli, one of the most stylish Italians of the 20th century, wore his watch over his shirt cuff shouldn’t lead lesser mortals to conclude that 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.

  • Boglioli Blue Slim-Fit Mélange Virgin Wool Blazer

  • Bremont U2/BL Automatic 45mm Stainless Steel and Leather Watch


  • Photograph by Mr Tommy Ton

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 fitting 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 wardrobe.

  • Caruso Blue Butterfly Slim-Fit Double-Breasted Wool-Hopsack Blazer

  • Bottega Veneta Round-Frame Bronze-Tone and Acetate Sunglasses


  • Photograph by Mr Yu Fujiwara

It’s hard to recommend particular quirks to emulate, because the whole point is that quirks should express individuality (“He’s ‘the crazy sock’ guy in accounting!”). However, in this shot we see a number of popular Italian tricks. The first is the turning back of shirt cuffs over the jacket’s sleeves. Note the way the lengths of the shirt and suit perfectly correspond. The same turn-back reveals at least four bracelets piled up on the wearer’s left wrist. In the background the man in the blue houndstooth jacket has unbuttoned a couple of his cuff buttons (this gesture originated so men could demonstrate that their jackets had working buttons, giving the impression that their clothes were bespoke). Note the juxtaposition of the working buttons and the wallet chain, an accessory we first saw worn with tailored clothing by Milanese style icon Mr Lino Ieluzzi. The challenge here is to find subtle individual idiosyncrasies without straying into the realms of ludicrousness (we think chain wallets usefully push at the boundaries, while ankle bandanas are a step too far).

  • Prada Grey Slim-Fit Checked Virgin Wool Suit

  • Gucci White Slim-Fit Bib-Front Double-Cuff Cotton-Poplin Shirt


  • Photograph by Guerrisms

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 Mr Alessandro Squarzi, a fashion consultant, 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.

  • Aspesi Cotton-Twill Field Jacket

  • Loro Piana Alfred Button-Down Collar Puppytooth Brushed-Cotton Shirt


  • Photograph by Mr Tommy Ton

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 this group of gentlemen proves. 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), the cotton cargo pants and the brown shoes. This might not be the ideal look for a day spent in a lawyer’s office but it would be perfect for a weekend lunch in a decent restaurant

  • Officine Generale Cream Slim-Fit Cotton and Linen-Blend Blazer

  • Incotex Slim-Fit Stretch-Cotton Twill Chinos

The men featured in this story are not associated with and do not endorse MR PORTER or the products shown