Jan Rogozinski tackles this topic head-on in his A-Z encyclopedia, Pirates. He comes down firmly in the “No” camp, describing them as a “fictional pirate accessory.” In a short but closely-argued entry, he points out that during the “Golden Age” of piracy, earrings were briefly fashionable at court, but fell out of favour when men began to sport longer hair-styles.
He adds that earrings don’t appear in contemporary illustrations of pirates in books such as Johnson’s 1724 General History or Exquemelin’s 1678 Buccaneers of America. He points a finger at 19th-century illustrator Howard Pyle who, almost single-handed, created the romantic visual stereotype of the pirate that still prevails today. The picture above of an earringed pirate appeared on the contents page of Howard Pyle’s Book of Pirates.
However, separating earring fact and fiction is as difficult as disentangling an earring from a pirate’s matted mop of hair. There is a tradition of mariners wearing gold earrings as a kind of coffin fund in case they were drowned, and washed up naked and anonymous on a foreign shore. The gold ring in the ear of their corpse, they supposed, would pay for a Christian burial. (Call me a cynic, but my guess would be that an 18th-century beachcomber would take the earring, and leave the corpse to rot in the sun.)
There are also mariners’ superstitions about ear-piercing: it protects you against drowning; it improves improves night-vision, or the sight in the eye on the side opposite to the pierced ear; it relieves sea-sickness.
So what’s the truth? looks like the jury is still out.