Simone Rocha! Thom Browne! A Ralph Lauren return! The Pitti Uomo trade fair and Milan Fashion Week Men’s show schedules this season are enhanced by some very exciting guest designers. Against a continued backdrop of supply chain and retail challenges in Italian menswear (and luxury as a whole), it’s a welcome dash of oomph for the industry’s flagship events.

“This season reflects the strength and international relevance of Milan, particularly at a time when the global fashion industry is facing significant challenges and transformations,” says Carlo Capasa, president of Italian fashion council Camera Nazionale della Moda Italiana (CNMI). “One of the most interesting aspects of this edition is the diversity of the calendar. Alongside the leading Italian brands, this season welcomes Thom Browne and confirms the presence of Ralph Lauren, further highlighting Milan’s international appeal and its ability to bring together some of the most influential voices in global fashion.”

Here are the brands and events to note.

Pitti Uomo

Pitti Uomo returns to Florence for its 110th edition from June 16-19, bringing together over 720 brands from across the world, 48% of which will be international. It’s the first fair under the new Pitti Immagine CEO, Ivano Cauli. Each edition of Pitti has a different theme that inspires an installation in the fair’s central piazza. This season, the theme is ‘swimming pool’, with a conceptual installation by artists Philéo Landowski and Pascal Hachem, to represent a ‘spring of talent’, Cauli says. It’s also to show “that the times we live in are mobile, fluid and uncertain, but we must still dive in.”

For sure, Pitti Uomo has not been immune to the challenges facing menswear or the broader challenges facing Italian fashion. In a speech ahead of Pitti Uomo, Cauli noted that 26,000 multi-brand stores closed in Italy alone over the last five years, and the menswear market declined 1.7% to €9.38 billion from 2024 to 2025. But the fair continues to scale despite this adversity. “We are expecting, as we see when the market is difficult, that Pitti Uomo will perform well,” he said, “[brands] need to understand also from a supplier point of view what's going on, what to do, and what is the right way forward.”

The Pitti Uomo guest designer programming is strong this season, led by Simone Rocha, who will present her first-ever dedicated menswear show on Friday evening. “The debut all-menswear show from Simone Rocha will be the undisputed highlight, runway-wise,” says Vogue’s chief international correspondent, Luke Leitch, who thinks it may feature more of the Adidas collaboration the designer debuted at her co-ed London show in February.

“I am excited to share the length and breadth of my menswear proposition, especially with the backdrop of beautiful Florence,” Rocha said in a statement. “I look forward to a new chapter in my work and world, playing with tradition and exploring new ground. I approach it with authenticity and vulnerability, seriousness and playfulness.”

Alongside Rocha, Dover Street Market brand DSM Kei Ninomiya, from designer Noir Kei Ninomiya, will take the second guest designer slot, hosting a late-night show concept at 10pm on June 18. Known for his highly creative and conceptual collections shown during Paris women’s, the designer will present his first ready-to-wear outing.

Elsewhere, South Korean designer Jiyong Kim will present his unique, sun-bleached garments as the third guest designer, showing at midday on June 17. “I hope to see Jiyong Kim a little more extensively than I was able to when we spoke during his presentation for the 2024 LVMH Prize,” Leitch says. “His process of incorporating sun-bleaching as a natural weathering effect in his clothes is an interestingly anti-technological gesture that produces some attractive clothes.”

“There is a great roster of guest designers at Pitti this edition,” says Bruce Pask, AVP, men’s fashion office, Saks Fifth Avenue and Neiman Marcus. “I’m excited to attend the first-ever menswear runway show from Simone Rocha, and am also looking forward to seeing Kei Ninomiya’s debut show for his new DSM collection. Hot Danish brand Sunflower will present a new collection as part of a partnership between Pitti Uomo and Copenhagen Fashion Week, which is celebrating its 20th anniversary. Polimoda will present its senior collections on the runway on Monday, which is always inspiring to see. And the Fortezza will certainly be filled with compelling new spring collections from an array of brands including Brunello Cucinelli, Stefano Ricci and more.”

Milan Fashion Week Men’s

Milan Fashion Week Men’s has a healthy dose of newness for SS27, with visiting names and fresh brands joining the lineup. The week will feature 16 runway shows and 44 presentations, along with a scattering of appointments and events across the city.

New York designer Thom Browne will make his Milan menswear debut on June 22. The designer most recently staged his FW26 show in San Francisco during Super Bowl weekend, and has previously shown in Paris, New York, and Florence, during Pitti Uomo. But this is his first turn in Milan, where he’s set to bring a little theatricality to the more refined Italian fashion capital.

Plus, as promised by CEO Patrice Louvet, last season’s well-received Ralph Lauren menswear show wasn’t a one-off. The brand will return to Milan for SS27 with a menswear show combining its Purple Label and Polo lines.

“There is an exciting lineup in Milan this season. I’m looking forward to seeing what Ralph Lauren, Prada, and Thom Browne bring,” says Young-Su Kim, Bergdorf Goodman’s SVP and general merchandise manager for menswear and men’s fashion director, Bergdorf Goodman. “Ralph’s return to the Milan runway last season felt incredibly special, and no one interprets prep with the same authority or cultural relevance. And Thom Browne showing in Milan for the first time feels especially exciting.”

Prada is another expected highlight, experts agree, as Miuccia Prada and Raf Simons lay out their mood for the new season (famously, the men’s show reveals a new show set, which is then lightly altered for womenswear), alongside mainstays Paul Smith, Etro, and Dolce & Gabbana. Zegna will skip this season, to present a special show in Los Angeles on June 5. And, as with previous seasons, Gucci will not show during MFW Men’s, opting to show Cruise in New York earlier this month, and present a co-ed show in September.

“One of the distinctive elements of this season is that Milan Fashion Week Men’s should be seen as the first chapter of a broader story. While the menswear collections debut in June, the narrative will continue in September, when many brands will present co-ed collections bringing men’s and women’s fashion together on the runway,” Capasa says. “In this sense, the season unfolds across two complementary moments, reflecting the increasingly fluid and interconnected nature of today’s fashion calendar.”

To close out the week of shows, Armani designers Leo Dell’Orco and Silvana Armani will present for the first time together for Giorgio Armani, as they continue the legacy of the late founder and navigate the brand’s next chapter. The evening show will include the men’s SS27 collection, accompanied by a selection of pieces from women’s cruise 2027.

Of course, Milan menswear goes far beyond the shows. It’s the tailoring presentations, tucked away in palazzos and private piazzas, that truly cement the week as a nucleus of menswear. “This edition of Milan Fashion Week Men’s reiterates this vocation with a rich offering that goes well beyond shows as the main focus,” Capasa said in a statement. “Alongside runways, there will be numerous presentations and other events enlivening the city, with experimental formats and languages that respond to change and widen the conversation on contemporary fashion for men.”

“Kiton, Brunello Cucinelli and Brioni are always standouts [presentations], with their exceptional craftsmanship and refinement,” says Kim. “Tod’s is always a highlight as well — the combination of the collection, atmosphere, and crowd makes it one of the most memorable moments of the week.”

Beyond the big names, Pask says he is “always on the hunt and scouting new brands is a big part of my mission while in Milan,” and this season, there’s plenty to discover. Garcias, a brand blending Colombian, Italian, and American influences, founded by Nicolas Martin Garcia, will join the schedule for the first time. Plus, Copenhagen contemporary label Martin Quad and Tokyo-based brand Shinyakozuka will show in Milan for the first time as they aim to reach a broader international audience. (The latter was a guest designer at Pitti last season and was encouraged by the response from buyers and press).

“Supporting emerging designers remains one of the key priorities of Camera Nazionale della Moda Italiana. Through initiatives such as the Fashion Hub at Fondazione Sozzani, we continue to provide visibility and opportunities to a new generation of creative talent,” Capasa says. “Rather than focusing on individual names, what I find most interesting is the opportunity to discover new perspectives and authentic creative voices. Each designer brings a unique vision, and this diversity is one of the elements that continues to enrich Italian fashion.”

Many journalists, including myself, have bemoaned the lack of newness and streamlined calendar of Milan seasons’ past. But with the current roster, it feels like the event is right where it needs to be for SS27. “Some say that Milan’s menswear calendar is sparse these days, and I can see that point of view,” says Leitch. “The flipside is that this is a mindful menswear calendar designed for the cognoscenti, containing only the finest men-facing runway brands.”