Showcase that you know a thing or two about menswear in a black quilted gilet and a black crew-neck sweater. Complement your outfit with a pair of black leather casual boots for a dose of sophistication. During the winter season, when functionality is imperative, it can be easy to surrender to a less-than-stylish look. But this look is a clear example that you can actually stay warm and remain stylish at the same time in the winter season. Those who are curious whether you can still pull off cool casual looks after 40, you have your answer.