DECODING PITTI UOMO STYLE

It’s Florence’s bi-annual trade show that launched the careers of Jean Paul Gaultier, Gianfranco Ferré and Dries Van Noten. Most names that hold weight in fashion — Simons, Missoni, Armani, Valentino — you name it, they’ve presented at Pitti Uomo. For the 105th Edition this winter, and more than a century of blue chip mens fashion later, the event continues to play a significant role in spotlighting the industry’s biggest talents. This time around, Luca Magliano and S.S. Daley followed in the footsteps of Craig Green, Telfar, Virgil Abloh, Wales Bonner as Pitti’s special guest designer.

Regularly drawing an audience of fashion insiders from all over the globe, Pitti has become the breeding ground for street style’s bravest peacocks. It is sprezzatura ground zero, a term to describe ‘studied carelessness’, in substitute of forwardness. Because as the world’s most stylish men will have you know, the most memorable shows are those felt in the moment, rather than rehearsed.

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Take note from the godfather of sprezz himself, Gianni Agnelli, whose clever watch over shirt styling is still the movement’s ultimate checkmate. At Fortezza da Basso, the 16th Century fortress built by the Medici family where Pitti takes place, the contrived orthodoxy of menswear dress is continually broken, replaced by the most thrilling spectacle of colour-bashing and accessorising — and exactly the dramatic entrata for this piece: How to dress Pitti-level.

Tailoring is the pomarola of any good Pitti outfit. No, we’re not talking elementary moves like tapered trousers, but something that feels bespoke like it was made just for you. Whether it’s the Neapolitan artisans or the masters of tailoring in London’s Savile Row, the historic roots of menswear are unmissable at Pitti. If the 2000s The Sartorialist era was reminiscent of boardroom execs at Sterling Cooper, the present affair leans into more relaxed, free-falling shapes. Menswear staples are rearticulated as oversized silhouettes and as confirmed by sartorial veteran Nick Wooster, baring one’s Tuscan sun-kissed legs in shorts is Pitti-a-okay.

Then the dreaded make or break of a great foundation: patterns. An intimidating territory for most, our learned advice is classics are classics for a reason. Tartan, stripes, check; whilst leaving the more elaborate prints like paisley as accents in the form of a neck scarf (note Japanese buyer Hirofumi Kurino). Daring prints can work as we saw on the street snaps circa 2020 (cowboys and graffiti) — but balance is key with an understated sunglasses and footwear.

As for the fabrication, try linen, try nylon, or hell, spoil yourself with 150+ thread count. Just spending five minutes at the entrance of Fortezza you’ll realise, those friends aren’t tapping each others’ backs, they’re in fact, checking the fabric quality. When dissecting the details of a great outfit, texture makes all the difference. Your goal is to look alive, not look like a pencil drawing, remember?

FASHION AND FUNCTION

You’re here for a sartorial good time, but it’s still work at the end of the day. Find an accessory that supports your look with fashion and function.

FASHION AND FUNCTION

You’re here for a sartorial good time, but it’s still work at the end of the day. Find an accessory that supports your look with fashion and function.

But if Pitti-dressing was as simple as a nice suit, it wouldn’t be Pitti at all. Bags have a duty at Pitti and that’s when the accessories come into play. After all, it’s not a party, it’s a work event — so, fashion and function are a must. The messenger, oversized clutch and tote bag are all reliable, but hey, when you’re competing against the world’s most stylish, you gotta break some rules, right? Wear your micro bag like a medal and go for gold.

Layering is treated as a styling technique with skirt over trouser, sweater as scarf, vest over jacket and doubled up shirts showing up more than ever. Like fashion’s fave analyst @databutmakeitfashion reported, 65% of the Instagram account’s surveyed consumers are bringing the ‘sweater over the shoulder’ styling into 2024 — data doesn’t lie — and just outside the world of Pitti, ‘underwear over stockings’ is proving this philosophy is onto new levels of seriousness.

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In the last 15 years or so, streetwear has subverted traditional menswear codes. So much so that even the most hardened Brunello Cucinelli traditionalists might consider a pair of adidas Handball Spezial to soften their disposition. Footwear like loafers and sandals are refashioned (chunkier, taller, texturised) with others ditching dress shoes for hybridised sneakers like Kiko Kostadinov’s Tonkin or Martine Rose x Nike MR4 Shox — is it a sneaker or a mule? Nevertheless, it’s most definitely a refreshing invitation for those crossing their thousandth Loro Piana Summer Walks strutting through the gate.

Meanwhile, incorporating jewellery or fine accessories will make any outfit your own. Are you modern like Montblanc or dapper like S.T. Dupont? It could be a vintage watch, signet ring (if it’s an heirloom, even better), cufflinks, brooch, keyring or tie clip. Something to say, it was simply lying around in your possessions and wearing it without too much thought.

THE GREAT FASHION DEBATE

Trench or Car coat? Loafers or sneakers? Whatever it is, back your look with quality and detail. How else would you separate yourself from the rest?

THE GREAT FASHION DEBATE

Trench or Car coat? Loafers or sneakers? Whatever it is, back your look with quality and detail. How else would you separate yourself from the rest?

What a way to add a personal signature to your style than a personal quirk. If you don’t have one, cultivate one. “Fake it ’til you make it” until you forget you faked it. Perfectly ironed handkerchiefs, monogrammed dress shirts or only buying undergarments from the merceria, it’s got to be a little inconvenient to wane off other adapters, albeit easy enough for you to let the signature soak in season after season. Dedication pays off.

By now you’ll know dressing to Pitti-perfection takes a serious level of thought. Which leads us to grooming. A trip to the barber is one, but not having a single crease or fluff on your shirt is a power move. Invest in the lint roll.

Finally, our pro tip: the stylishness of your look is infinitely multiplied when you’re standing with an equally well-dressed group. So make stylish friends your final accessory. Prego.