Try teaming a blue denim shirt with blue jeans to put together an interesting and current laid-back ensemble. In the footwear department, go for something on the dressier end of the spectrum and round off your outfit with a pair of brown leather casual boots. During the winter months, when practicality is prized, it can be easy to surrender to a less-than-stylish look. This look, however, is a vivid example that you can actually stay toasty and remain equally stylish in the winter months. A great illustration of how to dress fashionably as you get into your 50s.