Hard proof that an olive blazer and a dress shirt look amazing when paired together in a sophisticated look for today's guy. Avoid looking too formal by finishing with a pair of dark brown leather casual boots. During winter, when warmth is above all, it can be easy to settle for a less-than-stylish getup in the name of practicality. However, this getup is a clear example that you can actually stay cozy and remain equally stylish during winter. This pairing is your answer to the question of what to wear as you step into your 40s.