This combo of a dark brown wool turtleneck and khaki chinos is undeniable proof that a straightforward off-duty ensemble doesn't have to be boring. Go down a more elegant route on the shoe front by slipping into a pair of black leather casual boots. During the winter months, when comfort is top priority, it can be easy to surrender to a less-than-stylish outfit in the name of functionality. But this outfit is a good illustration that you can actually stay comfy and remain equally stylish during the winter months.