Earrings
Caribbean pirates sometimes are shown wearing one or two brass or gold “Gypsy” hoops. In real life, European men wore earrings – but not hoops – only during the 16th century. Even women’s earrings disappeared during later eras, when long hair, wigs, or head-dresses obscured the ears. As hair styles became shorter during the 1500s, Spanish and English aristocrats sometimes sported earrings. The fad affected only court nobles, who displayed pearls and other jewels and not metal hoops. Sir Walter Raleigh, Sir Francis Drake, the earl of Cumberland, and Sir Anthony Sherley may have worn earrings at court, but they left them at home during voyages. In France, earrings briefly became fashionable under the homosexual King Henry III (1551-1589).
Earrings vanished during the 1600s, as aristocrats again adopted shoulder-length hair styles. In England, male earrings, unthinkable under the Puritans, were not restored with the monarchy in 1660. The origins of the hoop earring myth are obscure. There are no earrings in Exquemelin’s The Buccaneers Of America (1678) and Daniel Defoe’s General History (1724-1728). Earrings also are absent from 19th-century fiction, such as The Pirates Own Book (1837), Treasure Island (1883), and Peter Pan (1904). During the 1890s, Howard Pyle was the first major author to put earrings in texts and illustrations. His pirates sometimes flaunt silver and jeweled pendants rather than gypsy hoops.
Douglas Fairbanks wears hoop earrings in The Black Pirate, a 1922 comedy; but they are rare in the romantic swashbucklers. Errol Flynn is earringless, even in The Sea Hawk (1940) set in Elizabethan England. Tyrone Power sports hoop earrings in The Black Swan (1942), as does Anthony Quinn in the Against Two Flags (1952). Disney put earrings into Treasure Island (1950) but left them out of Peter Pan (1953). (Rogozinski, Earrings)
These may have been popular in pirate companies, as some believed that they improved eyesight. Early blindness was common for lookout men, perhaps squinting into the sun for hours at a time. However, it seems that the real reason for the wearing of an earring by nautical men was that it would pay for their funeral if they died on land. (Breverton, Earrings)