Such must-haves as a cardigan and a white and black dress shirt are an easy way to inject some class into your current casual rotation. To give your overall ensemble a dressier aesthetic, why not add a pair of black leather derby shoes to your outfit? If you're looking to keep warm during the cold months and look stylish while doing so, this look fits the bill. This pairing demonstrates that figuring out fashion at age 50 is not particularly hard.