While the main focus of the fair has always been on the clothes hanging on the stands, it's the street style parades in the Fort’s cobblestone squares that equally draws the crowds. The street style looks at Pitti tends to look quite different from that of London, Milan, and Paris because Pitti is the home of true menswear obsessives. The fair's sartorial, suit-and-tie formula and placement in Florence, a region known for its craft and slow-made authenticity—evident in everything from leather goods to wine and tailoring, has naturally attracted a more primmed male audience.

Some of Schuman’s top photo subjects for well-turned out tailoring include Pitti regulars like Milan-based designer Alessandro Squarzi, model and menswear enthusiast Richard Bediul, and other notable names like Norweigian Rain’s T-Michael and Suited founder Ashley Owens. It’s this inclusivity and diversity that makes people watching at Pitti so fascinating. It’s got a brand of hardcore, old school uber-masculine men’s style from traditionalists like menswear legend Nick Wooster, but you also get a wider global scope of the men’s tailoring scene with attendees like Nigerian siblings and style revolutionists, Gabriel and Sade Akinosho or South Africans artists like 26-year-old Trevor Stuurman. 

While Italian’s are certainly the stars of the show, the Japanese buyers and industry figures turn out with incredible verve. Mr Hirofumi Kurino co-founder of Japanese retailing giant United Arrows, is known to throw together Ivy League style better than anyone on an American university campus, as well as having the peculiar talent to wear everything from dad sneakers to neckties and printed blazers, and still look like the coolest man at the show. Other names like Mr Takahiro Kinoshita, who previously served as editor-in-chief of Popeye magazine is known for his hefty-rimmed spectacles and effortless preppy and nerdy style.

And of course we can’t go without mentioning the “Pitti Peacocks.” For its only here, within the walls of Fortezza da Basso that the curious phenomenon exists, a rare breed who arrive in perfect formation, dressed up to the sartorial nines in lavish suits, fabolous coats and carefully considered accessories in the hope of capturing the lens of the street style photographers.

Legend has it that the "Pitti peacocks'' were mainly an invention of the Japanese magazine LEON, a publication that took its inspiration from the choiwaru oyaji (which roughly translates as “bad-yet-cool old guys”) of Milan and Florence. Articles not only detailed the latest trends from Italy, they also delved into the minutiae of sprezzatura - the type of dudes who represent everything grounded and intelligent about Italian men’s fashion. Twice a year, the magazine would photograph these men at Pitti Uomo as part of it’s biannual special called Snap! which consists entirely of street shots. Like most Japanese magazine’s, the pages and photos within them were meticulously categorised by garment and details, providing a handy reference to those in need of sartorial inspiration.
 

While it is a regular occurance now for the events grounds to be packed full of photographers shooting the looks at the fair, back in 2010s and earlier, LEON was the first to have put a supposed "man in the street" at the centre of attention of magazines. It wasn’t until years later that social media and influential photographers like Scott Schuman would arrive on the scene and push men’s street style into the zeitgeist of Western media. 

What’s more interesting is that the "peacocks" were transversal in style, not just sartorial. On the contrary, the best of them already mixed vintage, workwear, ethnic and tailored garments in abundance. It’s only today that the Pitti Peacock has evolved into a stage show of models in loud suits and obnoxious accessories, most of whom are cast by brands and organised services.

When describing the Pitti Peacock menswear magazine The Jackal explained “the term refers to those narcissistic individuals who rock up at the show with nothing to do other than wander about in dismal outfits in an attempt to be photographed for their own pitiable vanity.” While the Peacock have always been a draw for the show's observers, they are certainly secondary to the true purpose of the event. For most, the Peacock represents a culture that runs counter to everything that’s grounded and intelligent about men’s fashion. For Italian men in particular, style is about subtlety and a sense of comfort and authenticity. It’s not about showing off, rather adding finesse. It’s what they call sprezzatura. "While the peacocks rely on brash patterns, bright colours and big hats to stand out from the crowd, the sprezzatura approach is altogether quieter, based on precise fits and subtly artful expressions of flare” explains Globe Style.


While the Pitti Peacock is a seasonal staple, the past couple of years has seen the flock wane as patterns in men's style have evolved. “Where were all the Pitti Peacocks?” asked Monocle in 2018. “These Italian men, who famously come dressed to the nines (in three-piece suits, top hats and the rest) and spend their days posing, were far less omnipresent than in previous seasons.” Many attribute this to the fact that a more casual style of dress was taking place across menswear, in particular the influence of streetwear.
 

"In the last 18 months, there’s been a microcosm of men who’ve done something different, and who are moving things forward” explained The Jackal in a 2018 review of Pitti Uomo 94. “They’re taking louche tailoring and dressing it down – throwing off ties and tired collars, embracing richer shapes, camp shirts, drapey fabrics, wide-leg trousers and luxe sneakers.”

This evolution hasn’t gone unnoticed. Pitti has been taking note and has been busy catering to the new generation of contemporary menswear enthusiasts by expanding its offering at the show. Areas like ‘Touch’ and ‘Unconventional’ are proof to this evolution and its embracing of diversity, while the introduction of high profile designers like Craig Green, Y Project and Virgil Abloh’s Off-White demonstrate how they are trading in tradition for something new and progressive that represents today's modern male archetype.

For most of us, the idea of wearing a suit after months of working from home where casual attire and comfort dressing have become the norm, and this retrospective of Pitti’s tailoring past might seem like its coming at the wrong time. But the shift to smartened-up style has been on the rise for some time - just not in the typical stuffy looks we have come to expect from formalwear. Brands at Pitti like Nanushka are putting forward more relaxed and softly constructed suiting ideas, while Japanese labels like J.Press are at the forefront of a trend championing a more youthful approach to the American trad aesthetic. 

What Pitti Uomo’s street style timeline has shown us is that suits, topcoats, button-downs, loafers, and their ilk will never truly go away. Instead, they continue to be remixed, repurposed, and re-contextualized to fit into whatever trend comes next. And the most avant-garde dressers will continue to have fun working them into their wardrobes in new ways.