When the setting calls for an effortlessly classic getup, go for a navy blazer and dark brown chinos. Turn up the dressiness of your look a bit by rounding off with a pair of tassel loafers. Many people suppose that just because winter is colder you have to sacrifice smart style, but that's just not true, and this outfit is a clear example. This combo shows that as a man over 40, you have a wide array of styling options.