A crew-neck sweater and black chinos? This is easily a wearable look that any gentleman could wear on a day-to-day basis. Let your styling prowess really shine by completing this getup with grey low top sneakers. During winter, when comfort is above all, it can be easy to surrender to a less-than-stylish outfit. However, this outfit is a bright example that you can actually stay cozy and remain stylish at the same time during winter. This combo is a good illustration 50-something guys can still very well draw compliments.