This is from the Virginia Gazette, 8 June 1769 showing how people tried to transport money in safety. Or perhaps this was a lifestyle choice.
“Bristol, May 17. A few nights ago among the passengers that were gong in the large stage from Bath to London, were two supposed females, that had taken outside places; and as they were going to their birth, it was observed that one of them had mens shoes and stockings on, and upon further search the breeches were discovered also. This consequently alarming the company, the person was ‘taken into custody, and confined that night; next day he was had before a proper magistrate, and upon a strict examination into matters, it appeared that he was a reputable tradesman of a neighbouring town; and having cash and bills to a considerable amount, thus disguised himself in womens apparel, to escape the too civil notice of the travelling collectors.” ie highwaymen.
This is not the first man in the Bristol area cross dressing. It does make me wonder why it was the shoes that gave him away. How many stubbly women were there back then? Maybe a veil would have helped.