Here, Man About Town brings you the week’s menswear cheat sheet.
Dsqaured2 hits the slopes
Closing the first day of shows in the Italian capital is Dsquared2, who just presented its Autumn/Winter 2026 collection in a snowed-under warehouse. There are a few things Canada-born twins Dean and Dan Caten consistently deliver on their runways.
Steamy garments that are more sensuale than spezzatura; iconic pop-culture moments, catapulting celebs from the FROW to the runway; and a full-on party. Tonight in Milan, they did all three. Celebrating what’s hottest in Canada right now, Heated Rivalry’s star Hudson Williams took the runway in a concoction of layered jackets, a potential hockey jersey peeking through a zipper, shiny skinny jeans, and boots equal parts ice skates and cowboy. Elsewhere in the collection, après-ski was served with humour: fluor accents covered sportswear-leaning pieces, while fur ruled collars and hats. Vinyl and leather trousers looked ice-proof (though we’re not putting them to the test) and some suiting peeked out from under oversized puffer jackets. Down the slope, straight to the club — it’s winter, the Dsquared2 way.
Ralph Lauren runways are back in Milan
Before Friday, it had been more than 20 years since Ralph Lauren hosted a runway show in Milan, with the American designer previously favouring presentations for its premium Purple Label.
But yesterday marked a blockbuster return to the schedule in the form of two back to back runway shows combining Purple label with Polo Ralph Lauren. First up came the collegiate bangers; tweed blazers, and chunky cable knits, with roomy leather totes and keepalls adding a some campus-crossing style. Then came the old-school hollywood tuxedos, and later camouflaged military jackets, worn with ball caps.
Next, Ralph Lauren’s prepsters went on an off-campus excursion, outfitted by cosy knits, beanies, and padded ski suits. “My Fall 2026 collections are inspired by the different ways men live, their individuality, their personal style,” read the accompanying show notes. It is this ability to lead in outfitting all of these different lifestyles that makes Ralph Lauren such beast – one that was back in Milan, in all its American glory.
Brunello Cucinelli explores freedom through craft
You might not immediately go to the king of cashmere Brunello Cuccinelli when you think of the great outdoors. But it is the freedom of exploring that inspired the label’s latest collection.
This is gear for the man who refuses to lower his sartorial standards even when on the move, no matter the scenario. Double-breasted jackets were beefed up with metallic hardware, and worn with cargo trousers and buttery suede hiking-style boots. Brunello Cucinelli didn’t stop at the practical stuff. Although refinement remained with the shearlings and suedes that underpinned the collection, including on hyper-practical rucksacks. The offering also explored the world you might encounter while enjoying the freedom of the great outdoors, playing with materials like tweeds and Donegal through lightweight design, and a fresher enriched colour palette.
Zegna swings open the doors to the family closet
Courtesy of Zegna
Zegna is one of those steadfast, family behemoth brands that Italy does really well. Its founder, Ermenegildo Zegna, first started producing garments from his mill back in 1910, for instance.
And like any mighty dynasty with closets full of the fancy stuff, it got into the business of passing things down with its AW26 collection, “A family Closet”, which was set in an imaginary wardrobe with very real items from Gildo and Paolo Zegna (actual, third generation members of the clan) that they inherited from their relatives.
The suits were a sublime mixture of swooshy, single breasted styles, and remixed double-breasted belters, with single horizontal button closures. Knits were oversized and slouchy, and there were double collar blousons, and bomber jackets in there, too. This was notably chilled-out, oozing with the sophisticated rizz that comes when you get hold of your grandad’s mad coat that everybody asks about, and you wear in your own way.
