A turtleneck looks so great when married with black chinos in a casual ensemble. Inject a more laid-back feel into this ensemble with a pair of athletic shoes. In the winter months, when comfort is imperative, it can be easy to surrender to a less-than-stylish look in the name of functionality. But this look is a bright example that you totally can stay snug and remain equally stylish in the winter months. Certainly a surefire option if we're talking dressing ideas for 30-something guys.