Pitti Uomo and Milan Fashion Week Men’s Cheat Sheet: Spring/Summer 2027

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.”

Street style during Pitti Uomo trade fair.

Photo: Acielle/ Style Du Monde

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.”