One of the remarkable characters I discovered while doing some transgender history research for my book was Lord Cornbury. He was the British Governor of New York and New Jersey in the colonial era (holding office from 1701-1708).
Edward Hyde, 3rd Earl of Clarendon, Viscount Cornbury
...Cornbury is reported to have opened the 1702 New York Assembly clad in a hooped gown and an elaborate headdress and carrying a fan, imitative of the style of Queen Anne. When his choice of clothing was questioned, he replied, "You are all very stupid people not to see the propriety of it all. In this place and occasion, I represent a woman (the Queen), and in all respects I ought to represent her as faithfully as I can." It is also said that in August 1707, when his wife Lady Cornbury died, His High Mightiness (as he preferred to be called) attended the funeral again dressed as a woman. It was shortly after this that mounting complaints from colonists prompted the Queen to remove Cornbury from office.