This combo of an overcoat and a black suit is a surefire option when you need to look truly stylish. Bring a laid-back feel to your getup by finishing with a pair of burgundy casual boots. In winter, when functionality is the priority, it can be easy to settle for a less-than-stylish look in the name of practicality. But this look is a clear example that you totally can stay comfy and remain stylish at the same time in winter. When it comes to outfit ideas for middle-aged men, this outfit suits almost any gentleman.