A tan hoodie and beige chinos matched together are a perfect match. Athletic shoes are guaranteed to add a touch of stylish nonchalance to your look. During the winter months, when functionality is everything, it can be easy to settle for a less-than-stylish outfit. However, this outfit is a striking example that you can actually stay warm and remain stylish at the same time in the winter months. When it comes to casual dressing ideas for middle-aged men, this combination is perfect.