Menswear month opened, as it always does, in Florence, before the circus moved north to Milan. Two cities, two very different energies. Pitti Uomo is the trade fair that somehow became fashion week's most atmospheric opener, a place where the clothes and the people wearing them have always been inseparable. Milan is the business end. Together, they tell you where men's fashion is heading for Spring/Summer 2027. Some of it is exactly what you'd expect. Some of it wasn't.

Florence First: Pitti Uomo 110

Simone Rocha: The Show of the Season

The guest designer slot at Pitti has hosted Armani, Gaultier, Yamamoto. The bar is set high. Simone Rocha used it to present her first independent menswear show, staged at the 17th-century Teatro della Pergola with its backstage fully exposed, which felt entirely appropriate for a collection about vulnerability and beauty.

The collection drew loosely from E.M. Forster's A Room With a View: an Irishman arriving in Florence for the first time, moving through romance and self-discovery. The clothes were exactly as delicate and specific as that sounds. Ruffled rugby jerseys. Elongated shirting. Pearl-button Venetian wool double-breasted jackets. Wide Oxford trousers that sat somewhere between formal and pyjama. Jockey racing tops in Clongowes Wood College purple and white stripes. The works.

Kei Ninomiya and the Quiet End of the Spectrum

While Rocha was the headline, Kei Ninomiya, the first label under the Dover Street Market umbrella to show at Pitti, presented his SS27 collection at the Complesso di Sant'Orsola. If Rocha was warmth and romance, Ninomiya was precision and restraint. Two different arguments for what menswear can be when it stops trying to be menswear.

The Collab You'll See People Wearing

Margaret Howell's MHL line revealed a collaboration with Dr Martens, built around a reinterpretation of the 1461 work shoe. Understated, purposeful, genuinely wearable. Exactly what a collab should be.

Milan: SS27

Ralph Lauren Comes Home

Ralph Lauren hadn't shown a menswear runway show in Italy in two decades. The return, his first Italian menswear catwalk in twenty years, was exactly as considered as that kind of comeback should be. The collection hit the collegiate notes you'd expect, but harder and younger: madras windbreakers in searing shades, red chinos, morning coats with boater hats, banners patchworked across rugby shirts, cricket jackets, and weekend bags. It had the energy of someone who knows exactly what they built and isn't apologising for loving it. The front row, predictably, was packed.

Dolce & Gabbana: Vacanze Siciliana

Dolce & Gabbana titled their show 'Sicilian Holiday,' and delivered exactly that: men in robes and branded trunks, linen shirts, silk pyjamas, crystal-embellished jeans, citrus prints, and broderie anglaise short sets. Maximalist, sun-soaked, completely uninterested in restraint. For the right audience, irresistible.

Brunello Cucinelli: The Free Thinker

Cucinelli framed this season around what he called ‘the aesthetic traveller’, someone who blends influences without losing their sense of elegance, whose style is cultivated, yet effortless. In practice: suede safari jackets, oversized leather holdalls, cable knits in salmon pink that had no right to look that good. Understated luxury done with such confidence it almost reads as casual. Almost.

Thom Browne Makes His Milan Debut

Thom Browne has never been on the official Milan menswear calendar. This season he was showing at Palazzo Serbelloni. The expected theatricality was intact; Browne doesn't do half-measures. His debut here is a statement: Milan is taking its menswear season seriously again.

Setchu Turns Ten

Satoshi Kuwata's Setchu celebrated its 10th anniversary this season, adding emotional weight to what was already a brand on a quiet upward trajectory. A decade in, Kuwata's East-West hybridity feels more refined than ever.

The Bigger Picture

What does this season actually say? A few things. Softness is having a real moment in menswear, not androgyny as a provocation, but genuine tenderness as a design value, as Rocha demonstrated. Craftsmanship and heritage continue to anchor the Italian houses, but the energy is in the newcomers and the surprising returns. Safari dressing has officially crossed from trend to baseline. And Milan, with its tighter, more intimate schedule this season (16 physical shows vs. Paris's sprawl), felt like a city that knows what it's doing again.

The clothes are good. In some cases, they're better than that.

SS27 menswear shows continue – stay tuned as Paris Fashion Week Men's follows.

Images courtesy respective brands.