For an outfit that offers function and dapperness, rock a navy chambray long sleeve shirt with navy jeans. Not sure how to finish off this getup? Rock brown leather casual boots to spruce it up. So as you can see, it's extremely easy to look amazing and stay cozy when chillier weather arrives, all thanks to getups like this one. This getup illustrates that even in your fifties you still have a wide range of style options.