Stylist: Alex Badia
Fashion Assistant: Martino Carrera
Models: Laurie Harding, I Love Models Management; Kely Ferr, Elite Model Management
Hair: Valerio Sestito, Freelancer Artist Agency
Makeup: Bonnie Caria, Greenaple
This season’s new tailored clothing delivers a sense of confidence and assurance—even on the bustling streets of Milan, where residents exhibit a particular Italian genius for dressing with relaxed elegance. Robb Report captured this sense of sprezzatura against a backdrop of the city’s historic brick buildings for its Fall Fashion Issue, showing you how to wear fall’s biggest trend.
Dressing down buttoned-up tailoring and imbuing suits with a relaxed flair is nothing new—Giorgio Armani perfected the look in the late 1970s when he removed stiff shoulder pads from his jackets and cut his suits in a way that fluidly showed off the wearer’s physique.
This season, designers like Brunello Cucinelli and MP Massimo Piombo took Armani’s signature softly shaped suits and made them modern, presenting trousers that were slightly cropped to show off sleek boots, chunky lace-ups, and even sneakers. These suits were then layered with hallmarks of casual dressing like thin-knit turtlenecks, bomber jackets, and chunky shawl-collared cardigans, striking an of-the-moment balance between smart and casual.
Outerwear in unexpected textures—think a supple calfskin trench coat from Ermeneglido Zegna or a shaggy alpaca robe-style coat from Canali—help tie these looks together. It offers fashion-forward ways to unite trousers and blazers paired in artfully clashing houndstooths and checks into looks that are as effortless as they are luxurious.