This combo of a light blue dress shirt and navy wool dress pants is a safe option when you need to look like a true expert in modern men's fashion. For times when this outfit is just too much, dial it down by wearing a pair of loafers. In the colder months, when functionality is everything, it can be easy to settle for a less-than-stylish look. This look, however, is a clear example that you can actually stay cozy and remain equally stylish during the colder months. This pairing demonstrates that dressing cool as you step into your 40s is easier than one might think.