Consider teaming a dark brown velvet waistcoat with a white crew-neck t-shirt to exude rugged elegance and class. And if you need to easily dress down your getup with shoes, choose a pair of black leather casual boots. Planning a well-coordinated combination can be a bit of a conundrum on its own. Enter uncomfortably cold temps into the equation, and the whole thing becomes even more difficult. No worries, this here is your winter inspo. As a 50-something man, you'll like this getup.