For a fail-safe casual option, you can't go wrong with this combo of a grey blazer and blue jeans. Add a pair of brown leather low top sneakers to the mix to avoid looking overdressed. During the winter months, when warmth is imperative, it can be easy to settle for a less-than-stylish look in the name of functionality. However, this look is a striking example that you can actually stay comfy and remain equally stylish in the winter months. Ideal if you're on a mission for some incredibly inspiring over-30 casual style.