Winter menswear trends out of Milan, including monochromatic palettes, oversized silhouettes, and fashion that embraces individuality.

Back in December 2023, our own Gerald Ortiz declared that there were only two correct outerwear choices for men: drapey topcoats or cropped jackets. A month later, that theory was proved correct by the ever-stylish attendees of Milan Fashion Week. And a full year after that, the sentiment remains true on the streets of the very same city.

On the final day of Milan Fashion Week's four days of menswear previews for Fall-Winter 2025-26, attendees discuss whether its possible to know that a man is Italian, by looking at how he is dressed.

The independent Italian fashion brand Simon Cracker denounced the luxury fashion system with an upcycled collection previewed during Milan Fashion Week on Sunday that riffed on what they see as bygone days of quality and creativity.

MILAN-There were fewer brands showing their fall men's collections in Milan, but there were plenty of ideas that left retailers upbeat about the season. The runway shows by Prada, Giorgio Armani and Emporio Armani and Zegna,

Here are the key takeaways from Milan Fashion Week Men’s Autumn/Winter 2025. As Vogue Runway ’s Luke Leitch puts it, there was a willingness to “both appreciate and undermine convention” in Milan this season, as designers explored less conventional styles and injected a sense of freedom into their collections.

After the JordanLuca fall/winter 2025 Milan fashion show, designers Jordan Bowen and Luca Marchetto surprised guests by getting married on the runway. The couple met in London in 2011 and founded their namesake label in 2018.

Miuccia Prada and her co-creative director Raf Simons described the latest Prada menswear collaboration unveiled during Milan Fashion Week on Sunday as raw and romantic.

Streamlined silhouettes, tailoring, and monogram looks dominated street style during men's Milan Fashion Week. They stunned with a hint of "American Psycho."

Prada’s Fall 2025 collection blends raw shearling, cowboy boots, and florals, showcasing cinematic creativity and humanity amidst challenging times.

Giorgio Armani’s menswear collection previewing on the final day of Milan Fashion Week was all about catching the light, which the 90-year-old designer achieved with shimmering textiles and a smattering of crystals.

So are crisp neckties, flowy topcoats, pleated trousers, sharp button-ups, polished loafers, and all other manner of dressy menswear classics. But that doesn’t mean you have to wear said classics in the traditional ways—a point that’s been proven again and again by the uber-stylish folks currently roaming the streets of Milan.