Extra dapper and practical, this laid-back combination of a navy denim shirt and blue jeans will provide you with variety. Choose a pair of brown leather casual boots for a masculine aesthetic. In winter, when comfort is crucial, it can be easy to surrender to a less-than-stylish outfit in the name of convenience. But this outfit is a vivid example that you can actually stay snug and remain stylish in winter. This combination is hard proof 50-year-old guys can still very well kill in the style department.