The Chandos portrait depicts Shakespeare as having a receding hairline, facial scruff, and a shiny gold hoop hanging from his left ear. Many renditions of Shakespeare’s image have derived from this portrait, also depicting Shakespeare to wear an earring.
The question is, did he?
Earrings were a common fashion on men during the English Renaissance. Sailor’s would wear them at sea to cover funeral costs in the event of their death, and the fashion caught on among courtiers in the 1590s. In Bill Bryson’s book Shakespeare : The World as Stage, he suggests Shakespeare would’ve worn an earring for the same reason men wear them today – “to show that they have an unconventional, adventurous disposition.” He also speaks of Francis Drake and Sir Walter Raleigh, also believed to have worn earrings.
In the 1577 text Description of England by William Harrison can be found the following:
Some lusty courtiers and gentlemen of courage do wear either rings of gold, stones or pearls in their ears whereby they imagine the workmanship of God to be not a little amended. But herein they rather disgrace than adorn their persons.
Despite the fashion of the time, it remains debatable whether Shakespeare himself wore an earring. There is no substantial evidence that the Chandos portrait was of the man himself, whereas the Droeshout engraving from the First Folio (1623), a far more likely depiction, shows Shakespeare without an earring. The bust on Shakespeare’s monument in Holy Trinity Church (c. 1623), also without an earring, is further evidence that makes it unlikely.