To celebrate the repeal of the Act of Proscription (1747) which made it an offence to wear tartan amongst other things, Scots everywhere wear tartan today. The repeal proclamation came on 1st July, 1782. After this date highland dress became a preoccupation of the landed aristocracy who donned the kilt as a form of parlour fancy dress. Prior to this wearing the kilt was considered uncouth but distinctly manly. The reason for the original ban was the fear Prince Charles Edward Stuart (1720 – 1788) would raise an army to take the English throne. The English Government decided to eradicate the clan families and destroy highland culture. After the Battle of Culloden (1746), the broken Jacobite cause saw Charles Stuart on the run. To avoid detection he dressed as a woman. The irony was the Young Chevalier was effete and prone to wear the refinery of an aristocratic fop or dandy, so he would have fitted well into women’s clothes. Flora McDonald spirited him passed the government troops as her companion Bette Burke.
Men cross dressing is a common subterfuge during hostilities either to escape or penetrate enemy territory. There are countless examples from history but the most famous would be the cross dressers of Missouri during the American Civil War (1961-65). The James Brothers i.e. Frank and Jesse, were confederate guerrillas who lived rough in the hilly terrain of Missouri. During the civil war they would secretly find enemy locations and kill their opposition. Often to gain close access to country brothels where union troops were being entertained Jesse would disguise himself as a young wench. Jesse was baby faced and passed for a good looking young girl. There is no indication Jesse was a cross dresser other than through necessity and would always keep his boots on for a quick exit.