Go for a pared down but casually cool look by opting for a white crew-neck t-shirt and black jeans. When in doubt as to what to wear in the footwear department, introduce a pair of white leather low top sneakers to this look. Planning a pulled together combo can be a bit of a conundrum on its own. Add subzero temperatures into the equation, and the whole thing becomes all the more difficult. Don't despair, this here is your wintry inspo. This one is a great and age-appropriate pairing for an over-40 gentleman.