This elegant pairing of a short sleeve shirt and navy dress pants is a common choice among the sartorial-savvy men. Get a little creative in the footwear department and finish off with a pair of black leather tassel loafers. Many people suppose that just because winter is colder you have to sacrifice smart style, but it's just not true, and this ensemble is hard proof. This combo demonstrates that figuring out how to dress stylishly over 30 is totally doable.