Of all the items The New York Historical Society has in its collection, one particular portrait of a person in a blue dress is perhaps its most controversial and mysterious. Though officially listed as “Portrait of an Unidentified Woman,” some claim it depicts Edward Hyde, 3rd Earl of Clarendon.

As the royal-appointed governor of the colonies of New York and New Jersey, it was expected that Hyde would pose for a portrait. What was unexpected was that he would chose to do so in a beautiful blue dress.

Being a cousin of Queen Anne, Hyde bore a slight resemblance to her highness. Whenever he could, Hyde would accentuate his likeness to her by donning dresses of the finest fabrics and putting his hair in the latest women’s styles. Politicians, civil servants, and visiting dignitaries were often shocked to be greeted by the governor in his choice of apparel. Hyde even took to wearing gowns and jewelry when he opened assembly sessions.

When questioned on why he would choose such an unorthodox style of dress, Hyde maintained that it was nothing but appropriate. He reportedly told critics, “You are very stupid not to see the propriety of it. In this place and particularly on this occasion I represent a woman (Queen Anne) and ought in all respects to represent her as faithfully as I can.”

Hyde also had a habit of playing pranks on people. He would often hide behind trees and jump out to scare the unsuspecting passerby. And while cross-dressing and childish pranks are harmless, the rampant corruption during his administration was not. Hyde readily accepted bribes, embezzled defense funds, interfered in local governments, and persecuted followers of the Presbyterian Church.

It is for these reasons Edward Hyde is remembered as one of the most infamous governors of New York and New Jersey history. But whether this portrait truly does depict him remains a mystery.