I, Cowboy. Or is that iCowboy, the latest Apple gizmo? The old or the new—either way, it was the title of Ennio Capasa's new Costume National collection. His mood board was covered with photos of the late, great cowboy Johnny Cash. In his later years, Cash—aided and abetted by Rick Rubin—turned to a decidedly different songbook than the country one on which he'd built a career. His cover of Depeche Mode's "Personal Jesus" is a golden-years masterwork. And Depeche Mode, themselves getting along in years, commissioned Capasa to design outfits for their latest tour, so it all comes full circle. What interested the designer about Cash's cover was the freshness of its approach, its spirit of reboot.

That's what Capasa set out to channel in his collection, which played loosely on a cowboy theme, reimagined as a sporty, casual undressing of Italian tailoring. There were silver tips on the shirt collars and even some blazer lapels, soft booties, and straw cowboy hats with painted brims. What there wasn't, really, was a lot of freshness. The collection had much that would qualify for standard-issue wearability, give or take a leather fringe top or two, but it was hard to see the new approach that was meant to be its raison d'être. Costume National's ability to make great pieces isn't in question; Capasa has been doing it for years, with an eye toward preserving the skill. "I love Italian tailoring," he said. "I work really hard at tailoring, which is a value we don't have to forget now." But he shouldn't forget either the restless innovation that once made his shows some of the most exciting on Milan's schedule.