Who was the US first cross-dressing governor?

Answer 1

Edward Hyde the 3rd Earl of Clarendon (also known as Lord Cornbury) was Governor of the New York and New Jersey colonies beginning in 1702 until 1708. There are several testimonies stating that Lord Cornbury liked to go out in women's clothing and would even conduct State business in his female attire. There is also a portrait allegedly depicting him in this state of women's dress. However, the validity of the painting has not been confirmed and is therefore, an unreliable source on the matter.