Make a black blazer and white chinos your outfit choice to achieve a proper and polished ensemble. Our favorite of a myriad of ways to complete this ensemble is with a pair of black leather double monks. During the winter months, when comfort is above all, it can be easy to settle for a less-than-stylish look in the name of convenience. But this look is a practical illustration that you totally can stay comfy and remain equally stylish during the winter months. This ensemble is something 50-something guys can wear with confidence.