For an outfit that's very simple but can be styled in plenty of different ways, wear a black overcoat with a burgundy crew-neck sweater. Complement your outfit with a pair of black leather dress boots to avoid looking too casual. During winter, when practicality is crucial, it can be easy to surrender to a less-than-stylish look in the name of functionality. However, this look is a bright example that you can actually stay comfortable and remain equally stylish in winter. An ensemble like this will help any 50-year-old gentleman outshine his younger pals.