Dial up the dapper factor in a sweater vest and navy dress pants. Bring a more casual twist to an otherwise dressy look by sporting dark brown derby shoes. During winter, when comfort is paramount, it can be easy to surrender to a less-than-stylish look in the name of functionality. This look, however, proves that you can actually stay comfortable and remain equally stylish during winter. On the hunt for fashion tips for 40-year-old guys? This combo goes straight to your inspiration folder.