From checks to military-style coats, here’s what stylish men are wearing in Florence.

There’s a reason designers choose to show their collections in certain cities and it’s not always the reason you think. Rather than being, say, the birthplace of the brand, the location is often picked for that city’s personality. While London feels like a playground and Paris is adolescent rebellion epitomised, Milan is more for the sophisticate. And if you’re an exhibitor heading to Florence for the biannual Pitti Uomo trade show, it’s very likely your wares could be overlooked in favour of what’s being worn between the shows. The fashion fair is renowned for the sartorial flair of its attendees, and as its popularity has expanded among menswear enthusiasts, the resulting street style on display has diversified and expanded. As well as the usual peacocking – the tailoring is, as usual, faultless – there were also subtle elements of sports and streetwear as well as a dash of workwear on display. All of which correlates with the assertion that the menswear landscape is undergoing a sea change, and we are very much here for it. Here’s five of our favourite looks from outside the shows at Pitti this year.

We’re not sure the organisers will agree, but we’re considering renaming this edition of Pitti “How To Wear Checks: 101”. The first rule being: start small, as is deftly demonstrated by this chap. He’s accessorised his full-length camel overcoat with a plaid tote roomy enough for a full itinerary of shows and is thus ready to pound the cobbled streets in search of them. Speaking of which, the bowling-style sneakers are an addition which throws a touch of Americana into the mix. Eclectic, yes. But a surefire way to modernise what might have been an otherwise classic look.

Pitti is well known for its preening, colourful peacocks in the summer months. During winter, things are a little less extravagant. Tones are more subdued, and outfits more restrained. But that didn’t stop this guy from combining a cricket sweater with some tartan trousers, a tweed blazer and a wax, logo-emblazoned jacket. And is that not one but two caps around his wrist? Judging by his facial expression, this all seems par for the course for him. Fair play for pulling it off.

These two seem to be enjoying themselves, don’t they? And, if you’re rocking outerwear with such aplomb, why wouldn’t you? On the left, we have a classic trench coat paired with a simple white sweater and matching white cap. Well played. On the right, where we have a masterclass in layering, things are a little different. For a bolder approach, he’s gone for a red tartan wool coat with a check shirt and what looks like a blue blazer and sweater. No need for the camera, pal, everyone else is taking photos of you instead.

A different approach to outerwear, here, sees two mates matching in double-breasted military overcoats. Like any good boyband will tell you, though, the art of dressing in harmony is all about not dressing exactly the same. Note the different colours of the coats and different philosophies when it comes to the layers beneath. On the left, a denim jacket and a nautical tee. On the right: a laid-back knitted sweater, jeans and sock-free boat shoes.

We’re affectionately referring to this dapperly dressed gent as “Hat Guy”, but that denomination somewhat diminishes the sartorial skill it takes to pull off this heritage-themed ensemble. The nonchalantly draped greatcoat, the tweed blazer, the repp tie, the hint of a silk polka-dot scarf. We could go on. It’s as if he’s grabbed everything off the shelves in Cordings and had it all immaculately altered by his tailor. In a good (and possibly ironic) way.

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

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