This outfit with a white crew-neck t-shirt and black chinos isn't a hard one to pull off and leaves room to more experimentation. When it comes to shoes, go for something on the dressier end of the spectrum by finishing off with a pair of tobacco leather derby shoes. A great example of transeasonal fashion, this outfit is a staple when spring comes. Combinations like this have a sophisticated air that befit guys over 50 very well.