Florence’s Fashion Architecture of Ease: Pitti Uomo’s Street Style is Tailored, Tempered and Timeless

A well-cut suit and long overcoat are always a good idea in Florence during Pitti Uomo's winter edition. Cover picture and photograph above by Andrea Heinsohn for DAM

Italy's foremost Renaissance city moves to its own sartorial rhythm, and during this season's Pitti Uomo it was that rhythm, subtle, assured, and quietly expressive, that set the tone. Away from spectacle and slogans, the city’s streets revealed a refined approach to menswear that upended mercurial fashion trends. What emerged was a collective mood: thoughtful dressing, ensconced in craft and ease, unfolding naturally against the austere architecture and elegant pace of the city itself, all captured by our Europe Editor and photographer Andrea Heinsohn

Hats of all styles, shapes and hues

were a feature at Pitti Uomo 109

FLORENCE has always understood the theatre of dress, but over the past three days, during Pitti Uomo's 109th edition, for Autumn/Winter 2026-27, the city’s streets became the most compelling runway of all. 

From the cobblestones outside Fortezza da Basso which hosts the more than 750 fashion designers and labels at the tradeshow, to the shaded cafés lining the Arno, menswear unfolded not as trend forecasting, but as lived style personal, assured, and considered. Gelid mornings brought out an array of hats from leopard-print fedoras to peaked caps, purple berets and curling cowboy stetsons. 

This season’s street style was marked by a confident quietness. The peacocking of past years has softened into something more nuanced: elegance over excess, intention over noise. Tailoring remained central, but worn with a looseness that suggested ease rather than effort. Double-breasted jackets were cut longer and lighter, often unlined, paired with softly pleated trousers that moved with the body. Shoulders were relaxed, proportions generous, and everything felt designed for real movement under the winter Tuscan sun.

Colour told its own story. Neutrals dominated ~ stone, tobacco, olive, charcoal ~ but were punctuated with moments of confident expression. A saffron knit under a linen blazer. A deep oxblood loafer grounding an otherwise pale ensemble. Pastels appeared sparingly, most often washed and chalky, giving pinks and blues a weathered, almost architectural quality. Nothing felt accidental yet nothing shouted.

Pitti Uomo street style is not about chasing novelty; it is about refining identity and in Florence, panache doesn’t shout, it converses

A euphony of different textures and greys

made a subtle & elegant statement of style

Texture, however, did the talking. Crisp poplin shirts rubbed shoulders with silks, raw linens, brushed cottons and soft symphonies in grey. There was a renewed appreciation for fabric as substance: materials that crease, patinate and age. Many looks appeared already lived in, as if style here was less about the moment and more about continuity.

Accessories were deliberate and restrained. Scarves, silk, cotton, and the occasional archival print, were knotted with nonchalance. Sunglasses were classic with a linear Seventies vibe rather than futuristic. Bags were practical: worn leather totes, canvas cross-bodies, document cases that hinted at work rather than display. Footwear ranged from impeccably polished derbies to softly beaten suede loafers, often worn without socks in true Florentine defiance of formality.

Perhaps most striking was the diversity of voices. Editors, designers, artisans, fashionistas and buyers each brought their own vocabulary to the streets, yet a shared respect for craft and individuality bound them together. Pitti Uomo 2026’s street style was not about chasing novelty; it was about refining identity. In Florence, style doesn’t shout, it converses. And this season the conversation has been richer, quieter, and more engaging than ever. ~ Jeanne-Marie Cilento

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