Pyjamas and a more gentle approach: Here's what we saw at the menswear shows in Milan

CNN

8 hours ago

The feeling of unease is one of the hallmarks of our times, with cost of living increases and geopolitical conflicts contributing to a sense of disquietude. Within fashion, there is just as much uncertainty amid the ever-changing roster of designers at major luxury houses and a challenging retail climate.
That mood was reflected at the Spring-Summer 2026 menswear shows in Milan, where the collections were generally a mixed bag. But one thing several designers agreed on was the need for compassion.'The most important thing for us was a change of tone: an invitation to embrace gentleness,' Prada co-creative director Miuccia Prada told journalists after the show.
That sentiment was echoed by Italian entrepreneur Brunello Cucinelli. 'We need to find elegance, gentleness and embrace the art of listening to one another,' he told CNN at his presentation.
With introspection seemingly top of Prada's mind, the namesake designer and the brand's co-creative director Raf Simons sought to offer a calm and gentle respite to the troubled world. 'Basically, the opposite of aggression, power, nastiness, which seems to not interest me right now,' Prada told reporters backstage. The show, which was attended by the likes of Harris Dickinson, Riz Ahmed and Benedict Cumberbatch, featured dishevelled suiting, tiny shorts, hut-shaped intrecciato hats and striped tracksuits.
At Dolce & Gabbana, designers Domenico Dolce and Stefano Gabbana continued their exploration of heritage and Italian elegance, with a star-studded front row that included newly appointed brand ambassador Theo James. On the runway, models wore loungewear and versatile, slouchy separates, trousers with pleats and wide hems, oversized stripes across shirts and jackets (at times they mimicked pajamas), and leather pieces inspired by the 1980s.
Elsewhere, Brunello Cucinelli took a relaxed approach, offering classic, sometimes bold-colored, separates, inspired by the early '90s — viewed by some as a simpler time. 'The jacket is a bit shorter, while trousers are a bit higher and softer,' the eponymous designer told CNN. There was also a new capsule collection of cocktail evening-wear featuring jackets with satin-free shawl lapels, which were paired with silk-cotton knits.
The look of Italian fashion has evolved in recent years towards greater simplicity, sartorial rigor and a focus on form. The latter is key to Milan-based independent label Setchu, where its Japanese founder Satoshi Kuwata presented another collection of pragmatic and modular pieces. Inspired by the designer's fishing adventures in Zimbabwe, standout looks — such as garment bags turned into dresses, denim pants worn as skirts, shrunken blazers with peak lapels and straw hemlines — combined playfulness with functionality.
Nobody captures easy elegance better than Giorgio Armani. For the Italian label's latest collection, there was a shift towards greater fluidity, marking a departure of sorts from their typical suiting. Double-breasted jackets with shawl collars were shortened, while trousers either tapered at the ankle or hung loosely towards the floor. However, Armani himself was not present to take a bow; the 90-year-old designer was 'recovering at home,' according to a statement from the brand, without providing further details.
At Tod's, designer Matteo Tamburini leaned into unfussy pieces that had polished appeal. Describing the collection to CNN as 'relaxed elegance with a little touch of sportswear,' Tamburini used materials, such as compact linen, crepe cotton and ultra-light wool, that he felt would be comfortable to move around in.
British menswear stalwart Paul Smith, which normally shows in Paris, made its Milan debut with a show that expressed love for the city. Flea markets and vintage relics were references that defined the designer's joyful moodboard, which also took inspiration from a book of Cairo street photography. Guests, including actors Will Poulter and Daryl McCormack, sat on colorful food crates that were a nod to street markets. Among the key looks were pinstripe suiting, linen essentials and embroidered motifs on tops and outerwear.
Fellow British label Dunhill, which also migrated to Milan this season, dug into the elegance of Windsor men — in particular, the Duke of Windsor and King Charles, as well as British rock stars Bryan Ferry and Charlie Watts. 'What I love is that both sets of men adhere to a very classic taste but one group wore it in a very codified way and the others wore it in a much more effortless casual way,' Dunhill's designer Simon Holloway told CNN. 'In a way, the components were the same — incredible tailoring, incredible outerwear, haberdashery, the full gamut of the classic men's wardrobe worn in two very uniquely British ways.'
Elsewhere, London-based label Saul Nash returned to Milan for the second time (his first show took place at the beginning of the year) with a collection steeped in functionality, as he explored the power of human connection and designed with movement in mind. Nash is among a wave of independent designers finding their voice at Milan Fashion Week, which has typically been dominated by heavyweight brands such as Gucci and Fendi — both of which sat this season out.
Other up-and-coming names to watch include PDF, the Milan-based streetwear brand founded by Domenico Formichetti, which count racing driver Lewis Hamilton and rapper Central Cee as fans; and Simon Cracker, the Milanese label founded by Filippo Biraghi and Simone Botte with a focus on upcycling. 'It's about abolishing classist thinking and clichés and having a voice,' Botte told CNN.