Why did pirates wear earrings? Who knows, but it made you look pretty tough back then. They didn't have piercing guns either, no sir. They took the tip of their sword and just went for it. That proved that you were one tough buccaneer! We also had a lively discussion about this topic here in the office and decided that they probably found those earrings in the treasure chests they were digging up and we're just like, "Well, I might as well wear 'em," because pirates didn't see women that often unless they were living it up in Tortuga. That's probably not historically correct, but we learned everything we know from Pirates of the Caribbean.