This combination of a dress shirt and charcoal wool dress pants is a fail-safe option when you need to look really smart and elegant. Complete your ensemble with a pair of tobacco derby shoes to make the outfit more practical. In the colder months, when warmth is prized, it can be easy to surrender to a less-than-stylish ensemble in the name of functionality. This ensemble, however, is a striking illustration that you totally can stay warm and remain stylish during the colder months. All in all, a fail-safe choice when it comes to outfit ideas for men in their 50s.