One of the coolest ways for a man to style such a practical piece as a grey overcoat is to team it with a grey crew-neck t-shirt. For times when this outfit looks all-too-perfect, dress it down with a pair of tan suede work boots. This getup is a striking illustration that you don't have to give up style for functionality during the winter season. So if you're on the lookout for outfit ideas on what to wear as you reach your 50s, this combo is ideal.