For an outfit that's worthy of a modern sartorially savvy guy and effortlessly classic, team a dark green sweater vest with chinos. And if you want to easily play down your ensemble with one item, add black leather desert boots to the mix. You might think that just because you need to get bundled up you have to sacrifice your style, but that's just not true, and this outfit is a good illustration. Now that's how you do smart casual as an over-50 guy.