Though fall proves ripe with fashion inspiration—The elegant tweeds! The lovely thick knits! The buttery-soft suede!—winter can be a decidedly different story. It’s easy to fall into a rut, reaching for those weatherproof fail-safes again and again. So to nip any signs of sartorial stagnation in the bud before the season’s chill fully sets in, we’ve tapped Josh Peskowitz, menswear wunderkind and the newly minted men’s fashion director at Moda Operandi (a department the luxury retailer launched earlier this year). Here, he breaks down his six fashion-forward, cold-weather essentials, many of which are sure to brighten up even the dreariest December day.