Why not wear a blue denim shirt and navy jeans? These items are very functional and look nice combined together. With shoes, go for something on the dressier end of the spectrum and round off your getup with brown leather casual boots. Can you see how super easy it is to look on-trend and stay snug come cooler weather, thanks to this getup? This combination is a huge inspiration to anyone who was cautious about wearing casual clothing well into your 50s.