A sartorial masterclass from the streets of Florence and Milan.

The new year kicks off with Italy’s two big biannual fashion events, Pitti Uomo in Florence and Fashion Week in Milan. Media attention in Florence is almost entirely dedicated to the outfits worn by the attendees, while interest in Milan is spread more evenly between the clothes on the catwalks and the clothes on the street. All of this means that for the guys attending these events there’s an almost irresistible temptation to overthink their outfits, the result of which is that there’s great sport to be had reviewing the street-style shots. However, once you look beyond the men who dress like their mother didn’t pay them enough attention when they were children, there are plenty of stylish guys who remind us why we were so inspired when we first saw street-style images cropping up more than a decade ago.

If the eight men featured here share anything in common, it’s that each manages to look natural in their clothes, and all but one make tailoring seem relaxed and relevant. Now that dress codes are so relaxed, we rarely have to worry about what’s “correct”  anymore. This creates a need for sartorial role models who look beyond old-fashioned rules in search of contemporary ways to wear the classic styles. Sometimes this takes the form of wearing casual pieces like denim shirts with tailored clothes, sometimes it’s in the details of the way a garment is constructed and sometimes it’s just down to the personality projected by the wearer. Read on to find out what these eight men can tell us about how we can raise our game.

Sourcing great clothes is considerably easier when you have one of Europe’s best tailoring shops at your disposal, but Mr Andrea Luparelli of Rome’s Sartoria Ripense has more than just world-class resources to thank for his inimitable style. His appearance is remarkably consistent, and always includes a good week’s worth of beard growth, a few wrinkles and an enviable sense of ease. This particular outfit works thanks to the relaxed nature of the azure-blue open-neck shirt, the camel cardigan, the rumpled and rustic tweed jacket and the casual shirt-jacket (note the intricate sleeve head). The well-worn pair of peccary gloves work as a rugged and masculine pocket square, and the overall affect is a wonderful example of rus in urbe (country-inspired) style.

Pitti Uomo isn’t just about strutting around in elaborate tailored clothes. There are also plenty of men strutting around in elaborate casual clothes. Few, however, will manage to get it as right as this gentleman. Not many among us would be able to carry off an eight-piece baker boy cap made from loudly-patterned tweed, but here it works as an element in a well-balanced ensemble. The 1970s-inspired jacket is amazing and looks genuinely warm. The jacket’s slightly loose fit makes a relaxed impression that’s reinforced by the rock-star shades, and the colours are nicely balanced by the camel trousers.

When it comes to putting together an outfit, texture is as important as colour, and this photograph is rich in both. From the top down we’ve got the contrast between the soft curly hair, the rough beard and the acetate sunglasses. Then there’s that wonderful double-breasted overcoat with generous lapels, which is distinguished by its excellent shade of blue. Beneath that we see a cheery flash of colour in the form of a lemon-yellow corduroy jacket. Corduroy is much the most tactile form of cotton, and has a pleasingly rustic image even as part of a sophisticated outfit like this one. Yellow isn’t a popular colour, but on this evidence it’s unfairly neglected because it looks great next to the blue open-neck shirt. In this case there’s no need to introduce pattern to the outfit because the textures provide more sufficient visual interest.

Style sometimes exacts a price and in this case that price is a pair of chilly ankles. Of course, were it not for those short trousers, we might have overlooked the Norwegian style split-toe loafers and their substantial soles, and how their chunkiness contrasts with the silhouette of the slim-fit pinstripe flannel suit. We like the height of the generous turn-ups on the trousers, and the double-breasted overcoat, but most of all we like how the outfit isn’t fussy despite being put together with ostensibly formal elements. Three-piece suits rarely look this relevant, and that’s down to the soft shoulders, the way that the shirt and tie look so simple thanks to the black and white palette and the shirt’s soft collar.

You don’t need to embrace the athleisure aesthetic to benefit from introducing casual elements into your wardrobe. The men who are currently the best adverts for old-world tailoring keep traditional styles relevant by mixing them up with more casual pieces – think denim shirts worn under tweed jackets, blazers worn with vintage cargo pants, or old duffle coats worn over double-breasted suits. This provides the context in which we admire this man’s outfit. Sure, we see a smart-looking striped shirt and a dark tie, but the formality is toned down by the double-breasted Mackintosh and the corduroy cap. The roots of Mackintosh coats are as rugged weatherproof garments that prioritised utility. That’s a point reinforced by this coat’s raglan sleeves (which run from the collar to the cuffs, rather than connecting at the shoulder), which always carry informal associations.

Mr Luca Rubinacci, creative director of the Italian tailoring house that bears his name, has long been one of the stars of Pitti Uomo. The way that Mr Rubinacci’s style combines dapper details with a relaxed fit explains why there’s currently more buzz around Neapolitan tailors than their British counterparts. Take his overcoat, for example, which is relaxed and contemporary thanks to those soft, slightly extended shoulders, big patch pockets and that excellent stand-up collar. It’s a coat that could have come from a classic movie, but it’s eminently wearable thanks to those unstructured shoulders. Hidden beneath the coat there’s a hint of a tweed jacket, but the shirt and tie are more significant. The shirt looks smart, but the denim strikes a nicely casual note and the yellow tie pops merrily against it. Note the happy relationship between the generous width of the fedora’s brim and the width of Mr Rubinacci’s shoulders.

How do you stand out when many of the men around you approach dressing the way a child in a cinema foyer approaches the pick’n’mix? By throttling the sartorial volume right back, settling on one calming colour and nailing the details. This gentleman has taken inspiration from the colour of the urban environment around him and gone for a slim-fitting coat in a sophisticated shade of pale grey. It’s a colour that works well in the city, particularly in winter’s thin sunlight, and remains serious without being dour or excessively office-y. The rigour of the lean coat contrasts with the luxurious looking scarf, which stands out as much for its generous size as for the fact that it looks so warm. Top quality scarves are true investment pieces because you want the best fabrics next to your skin, and they never go out of fashion.

Very often the street style shots from Pitti Uomo are as useful for the things they teach us to avoid as they are for the things they inspire us to wear. The most common mistake is the adoption of the Christmas-tree look, which is achieved by men loading themselves up with a collection of disparate but eye-catching garments (presumably in the mistaken belief that this represents sprezzatura). Our man here has run that risk, but exercised just enough restraint to pull it off. There’s a nice correspondence between the casual denim shirt, the knit-tie and the blanket-cloth overcoat, while the extravagantly tailored houndstooth waistcoat contrasts well in colour and provides another strong element of texture. Meanwhile the military-inspired chinos are unobtrusively casual and act as a backdrop to the shiny ox-blood coloured double monks (it’s a shoe style that’s long been popular among the Pitti peacocks).

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