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What’s the Future of Men’s Fashion?

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THINK OF Disneyland. The color-coded map. The sprawling zones, each with its own attractions. The shoulder-to-shoulder bathroom lines. The selfie sticks. Now, imagine that instead of queuing up to ride Magic Mountain, visitors were waiting to rifle through racks of never-before-seen clothes. That’s Pitti Uomo, the largest men’s clothing trade show in the world, which last week marked its 93rd edition. Twice annually, retail buyers, fashion editors and general-hangers-on in Dick Tracy suits make the pilgrimage to a 481-year-old fortress in Florence, Italy, to go through the theme-park-like ritual over again.

It’s quite possible that the very clothes on your back—whether you bought them from Barneys.com or the boutique down the block, whether they’re traditional or trendy—were selected by buyers at Pitti Uomo. When the fair was founded in 1972 (it’s named for the Pitti Palazzo in Florence where early events took place), it was a bastion of classic Italian tailoring, but in today’s global, Instagram-happy trend landscape, Pitti Uomo has significantly, and confusingly, widened its scope. Labels from Japan, Finland, Nigeria and all corners of the world now populate its 1,200-plus booths. Among the pinstriped suits and calfskin brogues, you’re liable to find ostentatious designer tees (one depicted an emoji-fied version of Chanel designer Karl Lagerfeld, right down to his trademark ponytail and sunglasses) and Pollack-splattered sneakers.

Attendees capturing the circus-like atmosphere at the Pitti Uomo men’s clothing trade show in Florence. Photo: GETTY IMAGES

“Pitti Uomo is trying to find relevancy, and that’s a challenge because menswear itself doesn’t have an identity right now,” explained Simon Golby, the co-owner of Magasin, a boutique with two locations in California, as we walked the fair together. Yes, Mr. Golby was there to stock up on classics like Tricker’s dress shoes for his stores, but he also ordered elastic-waisted, double-pleated trousers from Devore, a new Italian label, and checked out the latest collection from California-based Monitaly, where a cheetah-printed fleece tracksuit hung at the front of the rack.

“This is the reality of the market,” explained Raffaello Napoleone, the CEO of Pitti Immagine (the parent company of Pitti Uomo) when I asked him about the breadth of looks on display, the aesthetic schism that mood-swung from the hush-hush haberdashery of Italy’s Luciano Barbera to the Ibiza-ready embroidered guayaberas I thumbed through at Hecho, an upstart Mexican label. “Our roots are as a suiting trade show, but today we have to set up a tree with many branches and opportunities.”

The week’s runway presentations also underscored menswear’s scattershot moment. Pitti’s fashion shows, which it has hosted since 1989, were initially a forum for homegrown Italian labels like Salvatore Ferragamo , yet as the fair has become more international in focus, so have the participating brands. Pitti Uomo is now a destination for ultra-creative shows from designers like Thom Browne of New York, Raf Simons from Belgium and Russia’s Gosha Rubchinskiy.

A model walks the runway in a corduroy suit during the Undercover fashion show this past week as part of Pitti Uomo in Florence. ILLUSTRATION: GETTY IMAGES

This season’s offerings were a tale of two extremes. On Wednesday night, Brooks Brothers held a runway show celebrating its 200th anniversary. The clothes were standard fare from the brand responsible for minting the American executive look (even if it has been owned for 17 years by the Italian mogul Claudio Del Vecchio ). The first outfit was a gold-buttoned, double-breasted navy blazer; the last, a tuxedo and patent-leather shoes.

The next night, in sharp contrast, avant-garde Japanese labels Undercover and Takahiromiyashita The Soloist put on back-to-back affairs. Undercover’s show was a “2001: A Space Odyssey”-inspired adventure replete with raincoats and a cape printed with stills from the iconic Kubrick film, while the Soloist struck a post-apocalyptic, road-warrior vibe with leather-sleeved sportcoats and inside-out jackets, tied up like harnesses on models’ backs.

But what do these opposing aesthetics—the conservative and the experimental—mean for you, the man standing on the sidelines while the clothes you’ll find in stores next fall are being plucked from the litter? You could certainly cherry-pick options from both ends of the spectrum and make them work (Undercover, in particular, had some crisp corduroy suits and a gorgeous cream-colored duffle coat that would play nice with the Brooks Brothers classics), but the two extremes left me wondering about the middle ground: Men need clothing that is interesting yet approachable.

A close-up of Italian designer Massimo Alba’s meticulously staged booth at the Pitti Uomo clothing trade show, held last week in Florence. ILLUSTRATION: MASSIMO ALBA

Many of the retailers I spoke with this week were excited about Italian brands like Massimo Alba, the Gigi, and Altea, as well as Japan’s Camoshita and Drake’s of London—all of which are finding new ideas in old ingredients. At Camoshita, I was taken with a notch-lapeled marriage of a blazer and a French work jacket that did away with the breast pocket and sat a bit slouchier on the shoulders. Leading a tour of his booth, Italian designer Massimo Alba presented a hoodie that looked like a standard-issue sweatshirt but was made from luxurious yak hair. It’s a sweatshirt for the Bobby Axelrods of the world—men who are successful enough to not wear a suit.

“My idea for the future is that everything must be blended together,” said Mr. Alba. Reach for the sweatshirt with the sartorial touches, or the fresh-from-the-factory blazer that slides on your shoulders as easily as a timeworn work coat. “We have to be open,” he added. Amen.

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