Five golden moments from Milan Men’s Fashion Week | Canada Voices

Mixed signals and mixed messages defined the Fall/Winter 2026 shows at Milan Fashion Week.

Hollywood stars filled the front rows, where even they were eclipsed by a major Heated Rivalry sighting. The “2026 is the new 2016” social media trend spilled onto the runways, and while silhouettes shrunk, conversations around diversity loomed large. Here are five takeaways from Italy’s style mecca.

Re-Heated Rivalry

More than any other designer showing at Milan Men’s Fashion Week, Canadian twin brothers and designers Dean and Dan Caten (of luxury brand Dsquared2) seized the spotlight by balking at any hint of Heated Rivalry fatigue and casting Hudson Williams (who plays gay hockey champ Shane Hollander in the series) in their runway show.

The clothes were the epitome of Zamboni chic: hockey pants accenting denim or reframed as shorts, fur-trimmed vests and puffers rendered in Toronto Maple Leafs- and Montreal Canadiens-hued palettes. The icing on the Dsquared2 cake was space age ski boots that looked like they were made for sloping in the 22nd century, further blurring the line between outerwear and indoor gear.

More than any other label, the Dsquared2 catwalk served as a cultural aperitivo to the upcoming 2026 Milano Cortina Olympic and Paralympic Winter Games. Forgoing a polite curtsy at the finale, the Caten brothers, wearing custom-made Dsquared2 hockey jerseys, concluded their show by striding atop the shoulders of two strapping young models.

Hyper-colour heritage

On Ralph Lauren’s runway, retro insignias and pixel knits popped off in a big way. Notable pieces included beige jeans with merit badge-style illustrations of footballers and pirate logos, green corduroy pants featuring mockingbird clip art, a Nehru-collared shirt with flying mallards and a red sweater with a cartoon rubber ducky on its sleeve. They were accompanied by knits with 1950s varsity Polo logos.

Swiss brand Bally also took a sketchy approach by adding cross-country skier graphics to a very cool parka and vest, while Dsquared2 showcased knits featuring 1970s-style prints of alpine skiers.

Denim reclamation

Victor-Hart took denim design to a new level with a show that reimagined the structure and texture of the material through diverse washes, abrasions and colour treatments. Fabric production specialist Haseller Textile collaborated on the process.

The refined interpretation of upscale workwear incorporated elements of the stonewash and acid wash aesthetics that were reconceived on runways in 2016, a year currently experiencing renewed interest. The runway looks featured capes, jackets, overalls, coveralls and collarless shirts in muted blues and greys, drawing inspiration from construction labourers in Ghana, Hart’s country of origin.

The designer’s selection of models reflected a diverse and inclusive vision of Italy, shaped by his experiences in both Ghana and Bologna, where he now resides. Hart’s approach stands in marked contrast to the recent Dolce & Gabbana show, which received significant criticism from fashion commentators for its lack of diverse casting, with many dubbing the presentation “50 shades of white.”

Deflation during inflation

Prada’s uber-narrow double-breasted suits and overcoats were a universe away from the volume of runway seasons past. Instead, the fashion house’s designs embodied what Forbes has called “The Ozempic Effect,” with slimmer sizing trends linked to the rise of GLP-1 drugs.

Menswear designer Zegna’s relaxed suits weren’t exactly oversized, but the 1930s-inspired grey and beige offerings were well-executed, with many pieces featuring three buttons at the waist.

Paul Smith’s proportions were a happy medium between Zegna’s looseness and Prada’s intense cinching. The British brand showed modernized wool poet jackets, intricately embroidered zip-ups and trench coats in loose but refined shapes.

New-old world

Giorgio Armani’s first show without its revered namesake designer at the helm (he died this past September) brought forth a plethora of nostalgia.

The collection was designed by Leo Dell’Orco, who has worked with the house for more than four decades. It tracks, then, that the show seemed more like a prequel than a sequel, reflecting Armani’s greatest hits as opposed to hinting at what’s to come.

The quality fabrics were there. The signature American Gigolo pleated pants worn by Richard Gere in 1980 were reimagined, along with fresh takes on the brand’s classic turtle necks, cardigans and shrunken microfibre jackets (in stone and oatmeal shades, mostly).

In stark contrast, streetwear brand PDF (headed by Milanese fashion rebel Domenico Formichetti), stepped up to the plate by remixing prints from camo to leopard on peacoats and separates. They’re clothes you can see his cadre of fans – Drake, Lil Yachty and Doja Cat among them – wearing to the club or to the Grammys. This was most evident in the show’s first look – a white and red gingham-print pant and shirt – as well as a 101 Dalmatians-inspired teddy fleece hoodie and tracksuits that blasted colour.