Team a dark brown turtleneck with black chinos and you'll look like the raddest dude around. You can take a more classic route on the shoe front by wearing tobacco suede chelsea boots. In the colder months, when practicality is paramount, it can be easy to surrender to a less-than-stylish getup in the name of convenience. But this getup is a practical illustration that you can actually stay snug and remain stylish in the colder months. This look is ideal for gents in their thirties.