Pairing a blazer and navy wool dress pants is a guaranteed way to infuse your day-to-day wardrobe with some masculine refinement. Complement your look with a pair of brown loafers and you're all set looking smashing. In the winter months, when comfort is key, it can be easy to settle for a less-than-stylish outfit in the name of convenience. But this outfit is a vivid example that you can actually stay comfortable and remain stylish in the winter months. This is a good-looking but also age-appropriate getup for a 40-year-old man.