Men’s Fashion Week Autumn Winter 2026 is underway, and the season is already shaping up to be one of contrasts. Designers are balancing classic tailoring with sporty practicality, and pared-back minimalism with bold, statement-making silhouettes. Across Milan (and later, Paris) the shows are signalling a renewed interest in winter dressing that feels both functional and expressive — a wardrobe for a colder season that doesn’t sacrifice personality.
Below, our favourite moments from Men’s Fashion month Autumn Winter 2026, as they happen.
Giorgio Armani
For his first collection without Mr Armani’s direct involvement, Leo Dell’Orco leaned into the house’s enduring codes: languid tailoring, plush textures and an effortless, lived-in elegance that feels instinctively Armani. Soft silhouettes flowed through roomy trousers, slouchy knits and relaxed suiting, while subtle injections of colour signalled a gentle evolution. Leather bombers and aviator jackets introduced a youthful undercurrent, nodding to an ’80s and ’90s revival without tipping into nostalgia. Shown in Armani’s intimate Milan headquarters, the collection underscored continuity, and an assurance that the house’s language remains as fluent as ever.
Ralph Lauren
For the brand’s first men’s show in nearly two decades, Ralph Lauren took to its Via San Barnaba atelier, for an intimate runway showcasing both Ralph Lauren Purple Label and Polo collections. The show was an eccentrically chic mash-up of the House’s many influences — from sharply tailored tuxedos and overcoats to technicolor Polo pieces inspired by retro skiwear, alpine knits and Western motifs. The result was a winter wardrobe that felt both heritage-rich and unexpectedly playful, complete with cowboy hats, pussy-bow collars and even New York Yankees caps.
DSquared2
For Milan Fashion Week AW26, Dsquared2 delivered a show that felt geared towards the luxury winter getaway of our dreams. The runway was transformed into a snowy, atmospheric scene, setting the tone for a collection built around bold, layered outerwear and aprés-ready silhouettes. Dan and Dean Caten leaned into their Canadian heritage, reworking hockey-inspired pieces (fitting, considering the show opened with Heated Rivalry‘s Hudson Williams, making his runway debut), oversized puffers and ski-style details into something distinctly modern and theatrical.
Zegna
Zegna’s latest offering doubled down on quiet luxury — clean lines, meticulous tailoring, and sumptuous texture. While the palette stayed largely muted, the details — from precision stitching to carefully considered proportions — gave the collection a subtle sense of drama.
Prada
At Prada, Miuccia Prada and Raf Simons merged sharp tailoring and playful, utilitarian detailing. Classic shapes such as topcoats and trousers were layered with more adventurous pieces, drawing out that sense of tension between tradition and rebellion the house is known for. The collection leaned into the idea of modern masculinity as something fluid and questioning, with details that felt intentionally off-kilter: exposed cuffs, unconventional hat shapes, and styling that suggested a refusal to conform to the usual rules of menswear.
