Try pairing a waistcoat with a turtleneck for a sleek sophisticated look. We're totally digging how a pair of charcoal leather double monks makes this outfit whole. During the winter months, when practicality is everything, it can be easy to surrender to a less-than-stylish ensemble in the name of convenience. This ensemble, however, is a stark illustration that you can actually stay cozy and remain equally stylish during the winter months. Now that's an outfit any over-50 gent will love.