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

John Turturro made an appearance in Zegna's fall/winter 2025 runway show during Milan Men's Fashion Week. See the surprising moment!

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.

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,

Instead of the usual bow, Jordan Bowen and Luca Marchetto staged their (very real) wedding to close their namesake brand's fall/winter 2025 runway show

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.

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.

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

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.

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.

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.