Putting together a shearling jacket with a crew-neck t-shirt is an on-point idea for an off-duty getup. For a more sophisticated finish, introduce a pair of burgundy leather derby shoes to your ensemble. Planning a killer combo can be a bit difficult at times on its own. Add subzero temperatures into the equation, and the whole thing becomes all the more difficult. No worries, this here is your wintry inspo. Men who wonder how to dress well well into your 60s, you have your answer.