At a Glance
- Dsquared2 staged a tongue-in-cheek Canadian Olympic tribute complete with hybrid ski-boot heels
- Ralph Lauren unveiled Team USA-inspired ski-lodge luxury before A-listers Nick Jonas and Tom Hiddleston
- Prada’s origami hats and paper-thin coats sparked front-row buzz
- Why it matters: Menswear’s biggest brands are betting Olympic nostalgia and utility chic will drive luxury sales next winter
The Olympic spirit dominated the final day of Milan Fashion Week menswear previews, as designers folded Games references, alpine utility and questions of diversity into Fall-Winter 2026-27 collections.
Olympic spirit
Canadian twins Dean and Dan Caten opened their Dsquared2 show with actor Hudson Williams-star of the gay-hockey drama “Heated Rivalry”-descending a fake-snow staircase in a ripped double-denim jacket and sparkly racing number. The designers, who founded the Italian label, used the moment to wink at missing out on outfitting Team Canada for the Feb. 6-22 Games.
Footwear stole the spotlight:
- Women wore a hybrid floating stiletto that snaps into a ski boot at the ankle
- Men got a similar mash-up of street and slope
- An intarsia gold medal decorated ski sweaters, though the twins stayed careful of IOC copyright rules
Across town, Ralph Lauren presented a patrician take on mountaineering inside a Milan palazzo. Colorful patterned knits, fleece jackets and puffers evoked the brand’s all-American heritage. Nick Jonas, Tom Hiddleston and Noah Schnapp filled the intimate front row.
“As a designer you feel the vibrations in the world,” founder Ralph Lauren said in a pre-show social clip. “If you are sensitive to that, you develop an ear or a feel for the clothes that you think you’re going to do the next season.”
Hats off at Prada
Co-creative directors Miuccia Prada and Raf Simons dedicated the season to men’s headwear. Berets and fedoras were engineered like origami, flattening so they could snap onto jacket backs.
Key pieces included:
- A modular cape that layers over coats for extra utility
- Dress shirts with T-shirt necklines that buttoned down the back
- Exaggeratedly long cuffs protruding from jacket sleeves, fastened with lapis-lazuli or tiger’s-eye cufflinks
The ultra-slim base-layer car coat divided critics, but Miuccia Prada was unmoved: “That’s fashion.”
She added: “Talking about intellectual honesty, we are working for a brand that sells expensive clothes to possibly rich people, and so you have to deal with beauty, elegance, to understand what is believable.”
Legacy and sustainability
Zegna creative director Alessandro Sartori showed a collection built to outlast trends-and generations. The house recently named fourth-generation co-CEOs, and Sartori wants clothes that match that longevity.
Stand-out item:
- An elongated, voluminous jacket with square shoulders
- Can be worn single-breasted, double-breasted or casually via three horizontal buttons
- Button-reversing mechanism allows styling versatility
Zegna controls about 60% of its supply chain, a rarity as other Italian brands face a supply-chain scandal. Behind glass, the label displayed a 90-year-old jacket cut from its own archival fabrics.
“Our customers are collectors, and not just fashionistas,” Sartori said. “I want people to collect pieces like watches.”
Simon Cracker, a 15-year-old upcycling brand, joined a small cohort of labels that can credibly claim sustainable practices on the Milan schedule.
Jewelry for men
Evening jewels emerged as a key menswear accessory. Dolce & Gabbana sent models in lapel brooches ranging from oversized florals to ornate gold pieces embedded with watches and trailing chains. Giorgio Armani added subtle lapel pins, while Prada finished looks with mismatched sculptural earrings.
Diversity and inclusion
Ghanaian designer Victor Hart debuted on the Milan runway with statuesque denim looks accented by industrial belting. His show was backed by the decade-old Afrofashion Association.
Milan’s fashion scene saw a short-lived diversity uptick after the 2020 Black Lives Matter protests, when designers Stella Jean and Edward Buchanan, alongside association leader Michelle Ngonmo, demanded change. Energy has since faded.
Casting models of varied races remains the easiest route to visible diversity, yet brands still stumble. Dolce & Gabbana, still recovering from 2018 ads critics called anti-Asian, showed an all-white cast Saturday and faced immediate backlash online.
French TikToker Elias Medini dubbed it “fifty shades of white,” while influencer Hanan Besovic behind @ideservecouture wrote, “having a cast of all white models in 2026 is diabolical.”
Key takeaways
- Olympic references gave designers a ready narrative for technical fabrics and alpine silhouettes
- Utility flourished in modular capes, convertible hats and hybrid footwear
- Jewelry stepped beyond watches into brooches and mismatched earrings
- Diversity debates flared again as some houses failed to broaden casting
