If you enjoy the comfort look, try teaming a black and white long sleeve shirt with jeans. You can get a little creative when it comes to footwear and dress up your getup by wearing olive leather casual boots. In the winter months, when warmth is the priority, it can be easy to surrender to a less-than-stylish outfit in the name of convenience. This outfit, however, is a striking example that you totally can stay snug and remain equally stylish during the winter months. Think middle-aged guys can't pull off modern off-duty looks? This pairing should prove you wrong.