Milan Menswear is a Dapper Affair

In 2025, well-executed accessorizing comes in many forms. A Labubu clipped onto a belt loop, when worn with confidence, feels clever and polished. A knit bonnet might pair seamlessly with combat boots. A vintage pleated fan can replace a clutch, if the right wearer wishes it so. Accessorizing is an ever-evolving art that thrives when paired with a rule-breaking attitude, and nowhere is it better on display than the streets of Milan during Spring 2026 Menswear Week—where the aforementioned examples were pictured en plein air.

Outside the shows, attendees embraced all sorts of embellished dressing. Three-piece suits were finished with suspenders, while colourful sheer button-ups brought flirtiness to the fashion capital. Tailoring was a major trend—but not in the way you might think. Traditional suits were reimagined at every turn: skirts replaced trousers, collared shirts were superimposed for a trompe l’oeil effect and wacky add-ons, from tall hats to trailing scarves, were plentiful.

These days, looking dapper is not restricted to the image of a classic suit and tie. As the Italian city’s sartorial scene proved, the most exciting fashion is full of colour, creativity and unconventional co-ords. Click through for 50+ noteworthy street style looks from Menswear Spring 2026 at Milan Fashion Week.

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Photography via Launchmetrics/Spotlight

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