Dressing for the cooler weather doesn’t necessarily mean bundling up, forgoing style and colour. The recent Milan Fashion Week Men’s Fall/Winter 2026 shows had plenty of proof of that. From Ralph Lauren’s statement-making preppy layers to Prada’s utterly slim and long coats, here are five of the best Men’s FW26 trends spotted at Milan Fashion Week.
Ralph Lauren
After two decades, Ralph Lauren returned to the Italian city’s Men’s Fashion Week, and where better than the Palazzo Ralph Lauren, its own private mansion in the heart of Milan. Hints of sombre winter palettes were nowhere to be found within the walls that were embellished with overgrown ivy under the soft chandelier lighting – it was instead a collection of warmth, colour and character.
The show presented two of Ralph Lauren’s most distinct menswear lines, Purple Label and Polo, interconnecting men from different generations. It was also a first-time affair to have both together down the runway. Purple Label showcased refined tailoring and material excellence, while Polo brought all the bold colours.
The collection conveyed the perfect embodiment of Ralph Lauren’s enduring DNA – part sporty, part preppy, yet designed for everyday dressing. Sport coats received a luxurious cashmere treatment, layered over graphic knitwear, while utility jackets and tartan trousers anchored the looks with function and familiarity. Meanwhile, trousers featuring fall foliage prints injected seasonal romance, balanced by rich fabrics like velvet, wool, and leather, designed to weather the upcoming seasons in style. Playful accessories took the wheel, including slouchy beanies, cowboy hats, and scarves draped over tote bags. As Ralph Lauren mentioned in his show notes, “I started with a tie, but it was never just about a tie – it was a way of living.” The words reflected on the many eras the designer has lived in and reimagined in the various ways men choose to dress today.
Prada
“A persistence of universal human values, values of civilisation – culture, meaning, intelligence, care – may be conveyed through clothes. Carrying impressions of life, they underscore the significance of duration. To remember is a sign of respect,” so goes the show notes for Prada’s Fall/Winter 2026 menswear collection by co-creative directors Miuccia Prada and Raf Simons. Aptly titled Before and Next, the vision rang crystal clear throughout the show.
The interior of Deposito of the Fondazione Prada, where the show was staged, resembled an Italian palazzo with soft pastel shades on the walls, complemented by warm wood panelling – except the wallpapers were stripped, floors were removed to reveal hollow depths, and fragments of doors and chimneys appeared to float against the walls. Crumbling debris lay exposed, erasing any sense of newness and replacing it with deliberate decay. The space was suspended by what once was and what is yet to come.
The same vision was translated onto the runway. The beauty of the pieces remained despite the “impression of life” they’ve encountered, visible through wear-and-tear marks, signs of imperfections, and worn-in textures. Thus, the intentionally soiled oversized sleeve cuffs – some even with scorched iron marks – raw-hemmed jackets, and leather pieces visibly scuffed and softened with age. The high-buttoning coats bore a noticeably stiff, slim and elongated silhoutte while, in contrast, trench coats (or mackintosh coats) were paired with colourful utility capes and matching sou’wester hats. On that note, there was plenty of headgear: bakerboy hats, bucket hats, hats that looked flattened. If anything, you can always count on Prada to deliver a show that leaves plenty of food for thought beyond the sharp tailoring and fashion statements.
Dolce & Gabbana
Dolce & Gabbana celebrated individuality with its The Portrait of a Man collection, where each look stood as a psychological and sartorial self-portrait. “There is no single way to be a man. There are infinite possibilities – each one deserves a portrait,” said the brand. The lightplay sculpted the silhouettes, evoking the emotional depth of Italian chiaroscuro.
Leave it to Dolce & Gabbana to reinvent the polka dot trend – spotted on ties, tops, and even trousers, all in monochromatic or vivid colours. Prints aside, the brand’s iconic Nero Sicilia (Black Sicily) colourway is presented alongside white shirts, flat caps, black knits and velvet suits, all while flirting at times with hues beyond the usual black and white. Think burgundies, greens, and midnight blues. Other classic patterns also make their appearances, from checks to herringbone to stripes.
Lapels were popped and lined with fur or knitwear, while accessories like belts, ties, and carabiners became the focal point of some of the looks. Tailoring played a fundamental role – the shoulders defined character, tailored trousers revealed sophistication, and materials, like deep velvets, dense wools, and contemporary brocades, brought forth the masculine essence.
Dsquared2
After celebrating its 30th anniversary last year, Dsquared2 knew just how to spark a conversation for its return to the catwalk – having the now-buzzing Heated Rivalry star, Hudson Williams, open the show. The actor wore a distressed denim jacket, skin-tight jeans and some chunky ski boots.
Skiing has been a recurring reference throughout Dsquared2’s history, with the inspiration stemming from founders Dean and Dan Caten’s Canadian heritage and long-standing fascination with alpine culture. This explains the co-ed show’s runway setup resembling a ski resort, with thick snowy mountains and trees acting as the backdrop.
Dsquared2 tested the limits for ski style with their provocative lens. Their signature denim use is elevated through exaggerated cuts, distressed finishes, and hybrid styling that blurs the line between utilitarian wear and fashion statement. With standout designs like low-slung jorts, bedazzled bomber jackets, puffer hats, and square-toed Western boots, the brand united the indie sleaze and ski resort aesthetics. The show closed with a lineup of womenswear of printed leggings, backless ski heels, and cinched corsets, all with a somewhat futuristic touch.
Giorgio Armani
Since the passing of Giorgio Armani last September, fashion enthusiasts have been pondering the maison’s new direction. Well, taking over the creative reins is Leo Dell’Orco, Armani’s lifelong friend who worked alongside the designer for 40 years. His debut show, titled Cangiante (which means iridescent in Italian), described a collection that remains entirely itself but shifts depending on the viewer’s perspective, whether an idea, a sign or a blend of colours.
The collection brought all the quintessentially Armani shades of grey, as well as dark hues, with occasional shimmery pieces peeking throughout. Oversized double-breasted blazers were paired with broad-shouldered overcoats and delicately draped knitwear. Overall, each pairing was wisely used, like felted wools with leather fabrics and velvet gloves with tassel bags, creating a sense of harmony. It was a collection that rightfully balances the house codes of Armani with Dell’Orco’s own fresh perspective.
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