A blue turtleneck and blue jeans are absolute menswear must-haves that will integrate wonderfully within your off-duty styling routine. When it comes to shoes, go for something on the smarter end of the spectrum and round off your look with tobacco leather derby shoes. This look is super comfortable and will help you out in winter-to-spring weather. This combination proves that cracking the fashion code as you head into your 50s is quite manageable.