Pitti Uomo, the menswear trade fair in Florence, held its first edition in September 1972, according to Pitti Immagine's own history page. It is still the room where Italian menswear shows its hand. Vogue reported that the June 2026 edition continued to perform well, with 730 global brands exhibiting, and UKFT's report on the 110th edition counted over 11,000 buyers at the Fortezza da Basso. When that many buyers walk the same fort, you can be sure of one thing: the stiff suit is no longer the point. Softness is. Start with the knit. Piacenza 1733 is a wool mill in Pollone, in the Biella textile district, with an official founding date of 1733, still family-run and old enough to belong to Les Henokiens. Its ribbed gray cashmere sweater is the one I would buy first. Altea began in 1892 when Giuseppe Sartori opened a tie shop in Milan, and its core business today is men's knitwear, so the half-zip in black virgin wool and the cream ribbed cardigan are the real specialty. Wear a half-zip under an unlined jacket. What I would skip is the orange Stone Island Ghost sweatshirt if the rest of the outfit is tailoring, since it belongs to a different conversation.

The shirt is where Italian softness turns into something you can wear on a weekday. Boglioli was founded in 1974 by brothers Mario and Stefano Boglioli in Gambara, Brescia, and it is known for tailoring and garment-dyed jackets, which explains why its green twill shirt feels relaxed without looking sloppy. Stone Island came out of Massimo Osti's Ravarino workshop in 1982, born from a heavy resin-printed military canvas called Tela Stella, and the name nods to Joseph Conrad's sea novels. Its black Ghost flannel overshirt is the one to wear instead of a jacket. De Petrillo's brown houndstooth wool overshirt does the same job with more Naples in it. For polos, Zegna's leather-trimmed piqué in white is the clean one, and Rubinacci's Sea Island cotton polo in black is the one for evenings. Bottega Veneta introduced Intrecciato in 1975, and Vogue says the weave began because the early workshop could not sew thick leather, so thin strips were woven instead. Wear a polo under a navy blazer with the top button open. What I would skip is the Zegna denim shirt with jeans, because double denim in the same wash looks like a uniform.

Trousers are where I judge an Italian label, and what I look for is simple: a soft waist and a leg that moves. Canali was founded in 1934 by brothers Giovanni and Giacomo Canali in Triuggio and is still independent, now in its third generation. Its tapered stretch-wool gabardine in navy is the dependable pair. Rubinacci began in Naples in 1932 as London House, was renamed in 1963 by Gennaro's son Mariano, and is now led creatively by grandson Luca. The Modaluca corduroy in navy is the pair I would buy for autumn. Barena takes its name from the barene, the marsh islands of the Venetian Lagoon, and says its clothing is Made in Venice, so its black garment-dyed houndstooth wool has a lot of character. De Petrillo's dark brown corduroy sits well with an oatmeal knit. Zegna's green Roccia jeans are the good option on Fridays. Pair corduroy with a smooth knit and flannel with a rougher one. What I would skip is the Stone Island wide-leg cargo trousers under a tailored overcoat, because the proportions fight.

Small things are where Italian houses show their age. Brunello Cucinelli started in 1978 with colored cashmere knitwear, which was unusual then, and in 1985 bought a ruined fourteenth-century castle in Solomeo, Umbria, as the company headquarters. Altea, remember, began as a tie shop, so its brushed gray cashmere beanie has some family pride behind it. Zegna's fringed Oasi scarf in brown takes its name from Oasi Zegna, the 100 square kilometer natural territory in the Biellese Alps that Ermenegildo Zegna shaped from the landscape around his mill. Piacenza 1733's navy cashmere scarf is plainer and I like it more. Gucci's first boutique opened in Florence in 1921, and its blue Vintage Feeling jacquard tie is the loud one in the grid. Rubinacci's printed silk tie in blue is the safer one. Mikia, a Japanese label founded in 1998 by Aki Mitsubayashi, supplies the bracelet, which is a good thing to wear with a plain shirt. Put the scarf on first, then the coat. What I would skip is the Sease cashmere baseball cap with a tie, because those two do not belong in the same outfit.

The thing I keep noticing about the Italian houses is how little they rely on a logo. A cashmere sweater from Piacenza, a corduroy trouser from Rubinacci and a garment-dyed shirt from Boglioli all earn their place by feel. If you are putting this look together, I would go in this order: one good knit, one soft shirt or overshirt, a pair of corduroy or wool-flannel trousers, and then a scarf. That is a full outfit and it will run from October through March. Wear the overshirt open over the knit and keep the shoes simple. Add the polo once the weather warms, and the tie for the evenings you actually need one. Let everything stay a little rumpled. Rubinacci's Neapolitan jacket is said to fold up to eight times, and a jacket that packs that easily is one you will wear more often, and the same goes for the rest of it.

Softness is a matter of cloth, so I looked for more pieces where the fabric does the talking. Trousers are the strongest group: the Canali straight-leg wool and tapered stretch cotton-twill, the De Petrillo cotton and silk-blend twill and the Stone Island mineral-dyed cotton gabardine-TC. Up top, the De Petrillo merino wool and cashmere-blend rollneck and the Altea virgin wool polo sweater are the knits, and the Zegna cotton and cashmere-blend twill shirt can sit over either. The Stone Island Ghost cotton-jersey tee keeps it casual. For the finish, there is the Brioni silk-jacquard tie, the Gucci Web-intarsia wool scarf and the Zegna Oasi cashmere baseball cap. What I would skip: the Brioni tie with the rollneck, since a tie wants a collar.