Consider pairing a charcoal blazer with grey wool dress pants for incredibly dapper attire. Why not take a more relaxed approach with shoes and complement your ensemble with white leather low top sneakers? During the colder months, when warmth is paramount, it can be easy to settle for a less-than-stylish look in the name of functionality. But this look is a vivid example that you can actually stay snug and remain equally stylish in the colder months. So if you need style tips on how to dress as you age into your 40s, this pairing is a great example.