To create a relaxed casual ensemble with a fashionable spin, you can wear a grey henley sweater and jeans. Clueless about how to complete your ensemble? Round off with a pair of brown leather chelsea boots to spruce it up. As you can see, this getup is a really nice idea, especially for summer-to-fall weather, when the temps are dropping. All in all, a good example of smart casual fashion for over-50 guys.