This sophisticated combo of a blue suit and a navy overcoat is a common choice among the stylish chaps. You can get a bit experimental on the shoe front and slip into chelsea boots. In the colder months, when practicality is the priority, it can be easy to surrender to a less-than-stylish ensemble. But this ensemble is a bright example that you totally can stay toasty and remain equally stylish in the colder months. Interested in outfit ideas for over-50 gentlemen? This outfit is pretty inspiring.