Pyjamas, Pimms and pizzazz: highlights from Milan men’s fashion week SS26

Dolce & Gabbana threw a pyjama party for SS26, taking the sleepwear classic they championed back in the 90s and giving it a beyond the bedroom makeover for day and night. In the searing Milan heat the cool crumpled finish of the striped PJ sets had wear-it-now appeal. (This was one of those instant impact collections where you immediately see the guests recreating the look the next day.) Perfectly styled with contrast-coloured boxer-short waistbands poking above trousers, sometimes layered with leopard print or broken up with polka dots, even the smattering of suits came worn over pyjama shirts. The eveningwear finale looks were scattered with diamanté and intricate bead work in floral designs that elevated the pyjama look further. The just-rolled-out-of-bed look has never looked chicer.

Giorgio Armani, who turns 91 next month, missed both the Emporio show on Saturday evening and his namesake show on Monday morning due to recovering at home from a recent illness. Leo Dell’Orco, Armani’s head of menswear design, took the bow in his place. Despite not being on site for the show his handwriting was written boldly over the collection. Armani’s signature relaxed tailoring aesthetic paired expertly with billowing chiffon shirts and silk pants. Patterns and decoration were inspired by Moroccan mosaics and Berber tents. Models carried carpet bags and wore the kind of souvenir jewellery that could be discovered in the souk. A strong edit of EA7 looks (Armani's sportswear line) designed for running in the desert wind opened the show.

Titled “A Change of Tone” Prada's SS26 outing saw the showspace at the Prada Fondazione stripped back to only large faux-fur black and white flower shaped rugs scattered across the sprawling floor. A complete reset from last season’s elaborate three-tiered scaffolding set with art deco carpet. In collection terms this meant a more dialled down approach; leather blazers worn with cropped trousers and neat rollneck base layers. Narrow-cut tracksuits came next, under macs and car coats (ideal for travelling). All in classic Prada colour combos: red and pale pink, splashes of bright green among neutrals. The Prada pizzazz came via glossed straw sun hats in white and block colour, boat-neck smocks and headline-grabbing shrunken bloomer-style shorts.

Next year Sir Paul Smith celebrates his 80th birthday and the venerable British designer is still keeping things fresh, choosing to make his Milan debut for SS26. Turning his Italian showroom into a show space, guests sat on upturned painted milk crates and the man himself narrated the soundtrack. An old book of Cairo street photography he rediscovered in his office was a starting inspiration for the collection. Collages using photos taken by Paul were assembled by hand and turned into bold prints and applied to shirts, outerwear, and ties – a technique pioneered by Smith when he first founded the company more than 50 years ago. The result was a concise edit of 30 looks showcasing tailoring, bold collage prints; including matching shirts and ties, and summer knitwear. Models carried string bags filled with fruit and veg and keepsake keyrings hung from belts.

Under the creative direction of Andreas Kronthaler, Westwood’s widower, Vivienne Westwood menswear returned to Milan fashion week after an eight-year hiatus. Taking over Bar Rivoli in the lively San Babila shopping district of Milan, models sauntered out of the café into the shopping arcade. Inspired by British dandyism with an Italian twist the collection referenced plenty of signature Westwood styles from punk to pirates, not forgetting the towering platform shoes. Tailoring was central; a grey stripe, high waisted, wide leg flowing trouser suit and bold gold chalk stripe with peaked lapels stood out. Other key pieces included a leopard-print faux fur coat and an apron that the waiting staff of the café donned while serving the guests breakfast cornettos and espresso before the show started.

The Homme Plissé Issey Miyake label decamped to Florence to kick off its Open Studio initiative that will see the brand show around the world to connect with local communities and the global creative scene. Ahead of Milan fashion week the collection was unveiled in the guest of honour spot during Pitti Immagine Uomo, a bi-annual menswear fair in the Tuscan city. Guests were bused high up into the hills to the picturesque Villa Medicea della Petraia, once owned by the Medici family. Titled “Amid Impasto of Horizons” the collection took inspiration from the landscapes of Italy and the colour palette took its cue from abundant nature, think pomodoro red, Sicilian lemon and deep aubergine accents. Some looks included handy pockets to stash paint brushes used to create impasto landscapes while others were daubed with paint effects. Origami looks folded up into garment bags and came complete with coat hangers.

Saul Nash’s motion-based design ethos fuses elements of sportswear and tailoring. Titled “Embrace” the SS26 collection is a study of sensuality through movement. “This season looks at movement through the interaction of two people, playing with hard and soft fabrics in a way that echoes the subtle language of touch,” he said in his show notes. Military-inspired flight jackets featuring Nash’s signature kinetic cutting technique are paired with adjustable trousers that can be unbuttoned to widen the leg. Other standout pieces included asymmetric fastening tops that unbuttoned to expose the nipple, water-resistant cotton hooded Oxford shirts and laser-printed tops featuring a motif of hands hugging the wearer.

Tuscan designer and LVMH finalist Niccolò Pasqualetti returned to Florence to show during Pitti Immagine Uomo. Showing on the roof of the modernist opera house in Florence on a baking hot June morning, Pasqualetti unveiled his fresh take on traditional menswear staples including military uniforms, classic workwear, sportswear, and tailoring. “The codes of menswear have always informed my desire for precision and for a certain freedom in dressing. I’m eager to evolve these codes while staying true to them,” he said via Instagram. Exciting garment development came via leather capes reshaped by draping or gathering, trousers that split open at the shins and shorts that flared out like skirts.

Creative director Simon Holloway took inspiration from dress codes of English aristocracy and their influence on the rebellious louche British rock icons. Described in the show notes as “the formal undone, the classic made rakish.” Think Bryan Ferry meets the Duke of Windsor. Models paraded through a garden while guests seated at tables flanking the catwalk path sipped pimms. Dunhill classic pieces like the car coat came in butter soft leather and suede, coated linen and cotton-silk twill. English elegance came through in summer combos of Madras checks mixed with stripes and primary pops of colour in jumpers jauntily draped over shoulders and baseball caps and candy stripe stripes worn with lounge suits.

Luca Magliano took a sabbatical from a runway show this season and instead hosted a screening for a short film directed by British director Thomas Hardiman. Set on a night ferry from Sardinia to Livorno in Tuscany, the story follows the antics of the diverse cast as they pass the time. The wardrobe has the air of being thrown into an overnight bag for a summer escape. Motif T-shirts mixed with exquisite tailored pieces, all with a soft worn feel – fabrics are mainly sourced from Italian mills. Clever design details like silk scarves fed through the lapel and under the collar of a jacket. Organza layers buttoned on to some pieces to mimic sea mist. Silk scarf dresses with trompe l’oeil prints and crochet doily tops.  Soccer shoes made in collaboration with Veja finish the look.

Creative director Hoor Al-Qasimi took inspiration from her brother, the late founder, Khalid Al Qasimi for the 10th anniversary collection focusing on cross-cultural exchanges. Staged at Sant'Eustorgio's cloisters, a former monastery, the mood was serene and contemplative. An art installation by Lebanese, London-based artist Dala Nasser took centre stage in the courtyard garden. Nasser’s influence is reflected in the collection’s raw edges, loose threads, and doodle stitching embroidery – all echoing her work with ancient Lebanese sites. Layering was key throughout the collection as was the use of memory nylon – a fabric that retains creases adding to the texture of a garment. A tonal colour palette of rich browns, beige, and sandy hues looked cool in the Milan sun. Utilitarian pocket details on shirts and bomber jackets mixed with softer mohair knits decorated with stones and buttons.