When the situation calls for a casually classic look, you can go for a charcoal wool blazer and a black crew-neck sweater. A pair of tan suede derby shoes instantly levels up the getup. In the winter season, when functionality is imperative, it can be easy to surrender to a less-than-stylish ensemble in the name of practicality. But this ensemble is a clear example that you can actually stay comfortable and remain equally stylish in the winter season. This pairing is a clear example men in their forties can very well slay in the style department.