This ad from 1985 portrays a man, presumably straight, dressed in women's lingerie to lightheartedly illustrate the inherent conflict between the male gender and the inconveniences of having a period. The idea is that Dr. White's feminine hygiene products will lessen the nuisance.
The depiction of this man as masculine apart from his lingerie supports the notion that crossdressing as ridiculous behavior.
Short blurbs of text melodramatizes the dilemmas that the advertiser imagines a man with a period might encounter, such as "I can't possibly clean the car with this nagging backache," "I'll never climb the ladder of success with legs this wobbly once a month," and "If you had sore, swollen breasts, you wouldn't want to be cuddled either."
While most straight men will likely be unaffected by these gender assumptions, the territory is more sensitive for those who might not meet such gender expectations.
To some consumers, Dr. White's approach to advertising might be funny, and a transgendered person might also see the ad as a joke. Other transgendered individuals would be offended by the reduction of a biological male who identifies as a female.