Ciao, Milano. All eyes are once again on the runway as menswear collections for spring/summer 2027 land in Italy’s style capital. The city’s relationship with fashion runs deeper than its glossy front rows suggest—shaped as much by disciplined tailoring and craft as by spectacle. This season’s lineup reflects that balance as familiar houses like Prada, Giorgio Armani, Paul Smith, Ralph Lauren, and Tod’s return to the calendar, alongside a growing contingent of labels new to Milan’s showcase—with Setchu, Garcias, and Martin Quad amongst those names.
Front and centre, though, are two shows that have set the tone for the week. Dolce & Gabbana opened with ‘Vacanze Siciliane’ on day two, the brand’s first runway since Stefano Gabbana stepped down as chairman—a Sicilian fantasy grounded in a deliberate evocation of the homeland that has always sat at the centre of the brand’s identity. Across town, Thom Browne marked his Milan debut, his first time showing his core menswear collection in the city since designing Moncler Gamme Bleu there nearly a decade ago. His menswear collection promises the same structured tailoring and uncompromising American sensibility he is known for, now filtered through a Milanese lens.
And what of the streets? With the sun out over Milan, the show-goers made the most of it—stepping out in sharp tailoring and summer-ready layers. Amongst the crowds, a familiar mix of fashion insiders and celebrity guests has emerged, with names like Enhypen, Troye Sivan, NCT’s Jaehyun, Lewis Hamilton and more spotted moving through the city. The Dolce & Gabbana presentation, in particular, drew one of the week’s most talked-about celebrity appearances, with TXT’s Soobin making his front-row debut. Across the city, a steady stream of familiar faces has moved between shows, underscoring Milan’s enduring pull as both a runway and street-style capital.
Below, peruse the best street style ensembles spotted from the spring/summer 2027 shows of Milan men’s fashion week, as photographed by Acielle of Style du Monde.

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