Resort season is beginning to wind down and while all is mostly quiet on the womenswear front, the industry is not done with international summer travel just yet. Mid-June brings the start of Pitti Uomo, a primarily trade-focused event in Florence, Italy, that kicks off the the menswear season. While Pitti can feel like a quieter affair in the grand scheme of fashion’s fabulous weeks due to the smaller number of big-name shows, there is no shortage of street style inspiration, especially for those looking for fresh takes on classic Italian sprezzatura.

That being said, there’s plenty on the runways to look forward during the spring 2027 menswear season, too. Vogue Business’s Lucy Maguire has laid out a cheat sheet for all you need to know for Florence and beyond, including news about this season’s Pitti guest designers Simone Rocha, Dover Street Market’s DSM Kei Ninomiya, and 2024 LVMH prize semifinalist Jiyong Kim. For Rocha, who began introducing her menswear vision in 2022, Pitti will be her first-ever standalone menswear runway show. “So far the menswear has been very hand-in-hand with the womenswear. Now I feel ready for it to stand on its own and be its own proposition,” Rocha told Vogue’s Luke Leitch in March.

Pitti began the tradition of guest designers in the 1990s, when the organization began inviting global names to stage one-off shows alongside the trade show’s exhibitions. “The value of this is that it makes Pitti something more than a fashion trade fair and something different to a fashion week,” Lapo Cianchi, Pitti’s director of communications and events, told Leitch in 2022. “Presenting fashion shows, installations or exhibitions on fashion culture and merging these with the commercial impact of such a big and well-curated trade fair is what makes Pitti different.”

Over the years, designers such as Raf Simons, Vivienne Westwood, Maison Margiela, Dries Van Noten, and Yohji Yamamoto have all found themselves on the Florentine runway. More recent examples include Magliano (the 2023 winner of the LVMH Prize’s Karl Lagerfeld Special Jury Prize), Grace Wales Bonner (who was recently named creative director of Hermès menswear), and Marine Serre. Scroll to see a sampling of the iconic guest designers, plus some of our editor’s favorites, below.

MM6 Margiela, fall 2025 menswear

Maison Margiela was first a guest designer at Pitti Uomo in 2006. Photos of the event are difficult to come by. At the show, Martin Margiela had models arrive in all white, save for reflective sunglasses, on the backs of mopeds and in cars. Twenty years later, Margiela’s little sister, MM6, took to Pitti for an equally cinematic showing, this time on an all-black stage. “The collection unfolded as a sleek, sophisticated, and sensual reinterpretation of classic menswear tropes, described by the collective’s spokesperson as ‘suggestive of different shades of masculinity,’ wrote Vogue’s Tiziana Cardini. “Marking the first full MM6 men’s show, the clothes reimagined traditional masculine archetypes with a distinct Margiela twist. Linen was coated and rubberized to mimic black leather; a tuxedo suit was crafted in tinsel-y turquoise lurex tearing open at the seams (“precious but also fucked up”), and black denim was airbrushed to give the effect of being lit sideways by a fading spotlight.”

Rolf Ekroth, fall 2019 menswear

I was only there in spirit, but in 2019 Rolf Ekroth, a professional poker player-turned-designer from Finland, scored big at Pitti Uomo. He showed his own line of outdoorsy clothes, some with anime motifs, alongside a collection he created for the sports brand Terinit, which he promoted with hockey, filming players on ice at home, and having helmeted models playing table hockey in the Finnish Pavilion.—Laird Borrelli-Persson, senior archive editor

Undercover, fall 2018 and The Soloist, fall 2018 menswear

Telfar’s banquet, JW Anderson’s tourists, Craig Green’s aura angels, Y/Project’s shadowy hyperkulturemia, Martine Rose’s minestrone. . . Pitti has served up some hard-to-overlook shows while I’ve been attending. But there’s no way to overlook fall 2018’s Michèle Montagne-orchestrated spectacular at which Undercover and The Soloist shared equal billing. The review in the links reveals my take from the night: looking back now what transmits across the eight years since is how Jun Takahashi’s Kubrick-inspired AI foreboding and Takahiro Miyashita’s post-apocalyptic survival tailoring both prefigured the future—which is what great runway fashion shows do.—Luke Leitch, chief international correspondent

Tim Coppens, fall 2017 menswear

My first (and only) time at Pitti was in January 2017, and it featured Tim Coppens as the guest designer. At the time, I was covering menswear at Footwear News, so I was mostly focused on reporting on his cool, chunky runway sneakers (made in collaboration with Under Armour). But in retrospect, the clothes still feel totally modern and fresh. The opening look was a bright-red shirt and pants with a brown checked blazer overtop, and it still feels like an interesting proposition—as do his track pant-striped trousers and knits that read “Never Ending Fun.” He was totally ahead of his time with this collection.—Christian Allaire, senior fashion writer

Raf Simons, 2003, 2005, and 2017; Jil Sander by Raf Simons, 2011

Raf Simons has decamped to Pitti a few times. First in 2003, when he staged a group show and co-curated an exhibition titled “The Fourth Sex,” with Francesco Bonami; then in 2005, for a 10-year retrospective with his radical “Icarus Surgit” collection; once during his tenure at Jil Sander for spring 2011; and finally, for spring 2017, shortly after he left Dior. The latter collection featured a comprehensive collaboration with the Mapplethorpe foundation. “The generosity of the Mapplethorpe Foundation’s offer is reflected in the generosity of Simons’s interpretation: There’s no outfit in Simons’s spring 2017 show that doesn’t feature a photographic print of a Mapplethorpe,” Alexander Fury wrote. “His curly-haired male models, with seductively slanted leather biker caps, often bore a striking resemblance to the photographer himself—though Simons stated that, rather than the artist’s doppelgängers, “every boy is a representation of a piece of work.”

Vivienne Westwood, spring 1991 ready-to-wear

As one of the first official guest designers at Pitti Uomo, Vivienne Westwood’s 18th-century aristocrat-meets-downtown-skater certainly made its mark. Both men and women sported floral brocade getups inspired by enlightenment portraiture—the result was a cast of courtesans fit for Westwood’s own costumed court. Appropriately, these ideas were contrasted by more common materials, like perforated and shredded denim and chunky cutout knit sweaters. High brow or low brow, the collection was a very debonaire affair.