A navy turtleneck and navy jeans are the kind of a never-failing off-duty combo that you need when you have zero time to spare. Up this whole look with a pair of brogue boots. In the winter season, when warmth is top priority, it can be easy to settle for a less-than-stylish getup in the name of functionality. This getup, however, is a good illustration that you can actually stay comfy and remain equally stylish during the winter season. And if we're talking style tips for 50-year-old men, this look is ideal.