The first thing that pops to mind is Roman emperors and generals like Pompey Magnus emulating Alexander's swept-back "anastole" hairstyle to appear more dashing. In fact, in studying Roman coins and busts, you can see how certain hairstyles, or the idea of wearing a beard, come in and out of "official" fashion. Usually, people argue that the move to change one's hairstyle is to reference a previous emperor or tradition--- either to appear bold and rugged, or stern and moral.

Although, the idea of something being "retro" is certainly specific to a particular time and place of late 20th century America, so I'm not sure if this really applies.

Sorry, we don't allow throughout history questions. These tend to produce threads which are collections of trivia, not the in-depth discussions about a particular topic we're looking for. If you have a specific question about a historical event or period or person, please feel free to re-compose your question and submit it again.