A Gentleman’s Guide

How To Dress Like An Italian

The six things that every Pitti peacock knows

  • 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?

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 the men there do to achieve their winning looks. Because wherever a man lives, there will be something he can learn from the world’s most stylish nation.

Make friends with chino and linen suiting

  • 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.

  • Boglioli Navy K-Jacket Slim-Fit Unstructured Linen Suit Jacket

  • Brunello Cucinelli Slim-Fit Cutaway-Collar Mélange Linen Shirt

Find a tailor who can execute a “shivering break”

  • 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.

  • Loro Piana Stretch-Cotton Twill Drawstring Trousers

  • George Cleverley Bradley 2 Leather Penny Loafers

You know what they say about a big sports watch

  • Photograph by Mr Tommy Ton/Trunk Archive

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 Signor 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.

  • Panerai Luminor 1950 3 Days Acciaio 42mm Stainless Steel and Leather Watch, Ref. No. PAM01537

  • Panerai Luminor Marina 1950 3 Days Acciaio 44mm Stainless Steel and Alligator Watch, Ref. No. PAM01312

The blazer is your canvas, the accessories your brushstrokes

  • Photograph by Mr Tommy Ton/Trunk Archive

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.

  • Mr P. Dark-Blue Unstructured Double-Breasted Linen and Cotton-Blend Suit Jacket

  • Rubinacci Navy Unstructured Double-Breasted Wool-Seersucker Blazer

Develop your own style signature

  • 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 hound’s-tooth 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 bandannas are a step too far).

  • Bottega Veneta Gold-plated and Leather Wrap Bracelet

  • Prada Logo-Detailed Saffiano Leather and Metal Wrap Bracelet

Add a piece of workwear to any outfit for some insta-cool

  • 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 Logo-Appliquéd Cotton-Twill Field Jacket

  • Brunello Cucinelli Slim-Fit Denim Shirt

Work within a limited palette

  • Photograph by Mr Tommy Ton/Trunk Archive

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 ideal for a weekend lunch in a decent restaurant.

  • Brunello Cucinelli Tapered Cotton-Blend Twill Cargo Trousers

  • Tricker's Leavenworth Leather Monk-Strap Shoes

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