Milan this season felt less like a parade of trends and more like a conversation about what menswear is holding onto and what it is ready to remix. Across the city, designers wrestled with ideas of legacy, identity, and desire. From heirloom tailoring to snow-swept theatrics, Milan proved that men’s fashion is at its most interesting when it remembers where it came from but refuses to stay there.
ZEGNA
Zegna’s Fall/Winter 2026 collection titled ‘Family Closet’ was anchored in the idea of clothing as something accumulated, shared, and passed down, drawing from garments that have moved through generations rather than seasons. Classic silhouettes like double-breasted coats, softened tailoring, and easy trousers crafted from the finest fabrics were designed to age with the wearer. Earthy, natural tones reinforced the sense of continuity, while quiet fabric innovations kept the collection rooted in the present. The message was clear: this was menswear built to be lived in, kept, and eventually inherited, not cycled through and forgotten.
DSQUARED2
Dsquared2 came in hot and unapologetically loud. Winter here was theatrical, sexy, and knowingly overdone, with ski gear, puffers, and denim colliding in a snow-dusted fantasy of athletic bravado. The runway leaned into sports references and pop culture with a wink, opening with Heated Rivalry actor Hudson Williams and pushing the brand’s signature camp-meets-machismo energy. It was not about practicality, and that was the point. Dsquared2 reminded Milan that fashion can still flirt shamelessly with excess.
DOLCE & GABBANA
With ‘The Portrait of Man,’ Dolce and Gabbana turned the runway into a gallery of personalities. Each look felt like a character study, rooted in the house’s long-standing codes of Italian masculinity but filtered through mood, tension, and emotion. The lineup leaned into sharply cut suits, sculpted coats, and body-conscious silhouettes, often styled in dark, dramatic tones punctuated by crisp whites. It was familiar Dolce and Gabbana territory, but approached with a reflective tone that emphasized individuality over uniformity.
PRADA
Prada’s Fall/Winter 2026 menswear collection focused on how clothes accumulate meaning over time. Miuccia Prada and Raf Simons worked with elongated, almost upright silhouettes, using high-buttoned coats, precise tailoring, and layered outerwear to draw attention to posture and presence. Utility capes worn over trench coats, quilted leather jackets, and collaged prints referencing antiquity and the Renaissance introduced a sense of historical layering without feeling literal. The palette stayed restrained and earthy, allowing texture, proportion, and construction to do the work. The result was a collection that treated menswear as thoughtful, considered, and quietly intellectual.
QASIMI
Qasimi delivered one of the most emotionally charged collections of the week. Hoor Al-Qasimi treated clothing as a carrier of memory, using deconstructed tailoring, layered fabrics, and distressed textures to suggest lives in motion. Oversized proportions, built-in scarves, and weighted drapes gave the pieces a sense of gravity, as if history itself was stitched into the seams. The result felt deeply human, thoughtful, and resonant.
GIORGIO ARMANI
Fall/Winter 2026 marked a poignant chapter for Giorgio Armani, presented under the guidance of Leo Dell’Orco following the founder’s passing. The collection stayed true to the house’s DNA of fluid tailoring and muted elegance, while gently nudging proportions closer to the body. Soft greys and neutrals were lifted by unexpected touches of iridescence and richer hues, signaling continuity rather than rupture.
BRUNELLO CUCINELLI
Brunello Cucinelli’s Fall/Winter 2026 collection unfolded as a calm, confident meditation on balance. Titled “Art Imitates Nature,” the lineup translated philosophy into clothes that felt instinctively right rather than overtly styled. Double-breasted pantsuits in a hybrid denim-corduroy fabric set the tone, luxurious but relaxed, while frosted corduroy, textured knits, and softly structured blazers reinforced the house’s signature ease. There were subtle military notes in leather trench coats and biker jackets, balanced by cozy tweeds, Donegal textures, and shearling-collared outerwear. A neutral, earthy palette was lifted with controlled hits of burgundy and ocean blue, resulting in menswear that felt harmonious, tactile, and quietly assured.
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