A round-up of the best looks from Milan Men’s Fashion Week, where luxury designers focused on a mixture of timeless styles and innovative outwear materials. It even included a surprise designer wedding.

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

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.

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.

Bowen and Marchetto then cut a huge wedding cake, which featured 3D-printed replicas of the happy couple on top, with their runway models gathered around.

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.

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.

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

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.

A household institution in bespoke tailoring, Rubinacci has serious ambitions for its growing ready-to-wear line — and is winking to women, too.