When the setting allows a casual outfit, try teaming a white check long sleeve shirt with blue chinos. Rounding off with a pair of dark brown leather snow boots is a fail-safe way to infuse a more casual touch into this look. In winter, when warmth is the priority, it can be easy to surrender to a less-than-stylish look in the name of functionality. This look, however, is a striking illustration that you can actually stay cozy and remain equally stylish during winter. Relaxed looks for stylish gentlemen in their thirties aren't actually that hard, as you can see here.