Make a dark brown waistcoat and chinos your outfit choice if you're going for a neat, sharp outfit. In the winter months, when warmth is imperative, it can be easy to surrender to a less-than-stylish ensemble in the name of practicality. This ensemble, however, is hard proof that you totally can stay toasty and remain stylish at the same time during the winter months. If you're wondering how you should dress as an over-50 gentleman, this ensemble gives a good idea.