Milan Fashion Week was particularly busy this season. Vogue World landed in the city, bringing a host of designers and models to the Galleria Vittorio Emanuele II on Fashion Week’s opening night. Not to mention Glenn Martens’s final showing at Diesel and the Moschino debut of Simone Rizzo and Loris Messina, as well as the opening of the “Dalí and Fashion” exhibition at the Palazzo Reale. All of which gave the city’s best-dressed plenty of reasons to step out. And in the city best known for its elevated ready-to-wear, it was hardly surprising that exceptional tailoring and luxurious craftsmanship came to the fore on the streets, too.
Arguably, the show of the season was Prada, and its devotees were quick to take to the streets in support of the much-loved brand. Statement skirts were a particular favourite, alongside oversized knitted scarves and grey wool tailored skirts from the label’s autumn/winter 2026 collection. Elsewhere, blue button-down shirts were another common sight, whether tucked into the aforementioned statement skirts or styled with jeans.
Featured in this article
Denim styles tend to ebb and flow from city to city, and, unlike the low-rise jeans favoured by the London street-style set, decidedly high-rise, straight-leg cuts were everywhere in Milan. They formed the foundation of many an off-duty model’s wardrobe, typically worn with a shrugged-on leather jacket and a simple camisole.
As for accessories, it was the bolder offerings that really stood out. Red shoes, from ballet flats and kitten heels to boots, were the street-style set’s answer to this year’s pop of colour trend. And one nostalgic bag style was practically everywhere: the Carrie Bradshaw-approved Fendi Baguette.
The most unlikely contender, however, as outlined by ’s shopping editor, Joy Montgomery, was the cummerbund. “For the uninitiated, a cummerbund is a sash-like accessory most typically worn as part of a traditional men’s black tie suit or tuxedo,” she wrote, “Cut to the present day and cummerbunds have become the latest in a long line of menswear icons that have been co-opted by womenswear designers.” The piece appeared across the autumn/winter 2026 and spring/summer 2027 collections at Polo Ralph Lauren, Kallmeyer, Talia Byre, Ahluwalia and Mithridate, and has already made its way around the waists of the street-style set in Milan. Whether worn over tailoring or used to add definition to a more relaxed silhouette, the accessory is proof that often the simplest trends are the ones that stick.
Scroll on to shop the street style trends to know from Milan Fashion Week, and discover the pieces to help you recreate the looks now.
The grey tailored skirt
The knitted scarf
Fringed Intrasia Knit Wool Scarf
The colourful crew neck
Christian Dior Monsieur Multi Coloured Patterned Silk Men’s Cummerbund
The statement skirt
Satin Floral Knee-Length Slip Skirt
High-rise straight-legs
The blue poplin shirt
The red shoe
Block Heel Chisel Toe Court Shoes
