This article appears in the pages of VMAN 42: Turning Point, on newsstands now. Order your copy at shop.vmagazine.com.

Trainers and runners have dominated the athleisure landscape, despite skateboarding shoes predating them as acceptable all-day footwear in the long arc of street fashion history. Now the Italian godfathers of streetwear have circled back to the flat-soled, kickflip-friendly shape—wallet chain and sagging pants not included.