For an edgy ensemble, Try teaming a black and white crew-neck t-shirt with jeans. Up the appeal of your ensemble by slipping into olive leather casual boots. In winter, when comfort is the priority, it can be easy to settle for a less-than-stylish ensemble in the name of practicality. However, this ensemble is hard proof that you can actually stay warm and remain equally stylish during winter. If you're not sure how to dress your age while looking fashionable at 60, this outfit is a fail-safe option.