Most Helpful Guy
I would argue it has to do with the perception of society. I don't think the artist was trying to deal with men dressing up as women, but rather he was trying to illustrate things like gender roles and what men and females should do.
Notice the hands. The man's hand holds a pen. The female hand holds lipstick. What the artist seems to be implying here is that society's view on the man is that of business. He is typically the worker and is portrayed as the "all-business" and leader-in-the-family type figure head.
However, the woman holds lipstick and is dressed in a skimpy dress, tons of makeup, pinned up hair, and just screams materialism. She represents society's pressure of and stereotyping of women to be the "token" or the stand-there-and-look-pretty type persona. It saying how women are perceived to be fake.
I would argue that them being conjoined (as in the two people being together) is basically stating the falsity of gender roles and stereotyping. It is saying that either side can do whatever they want to do and that humans are actually quite remarkably similar to each other. It is only society's pressure causing us to break away and choose the business side or the fake/makeup side. We have potential to be either, but the formation and stereotyping tells us to behave and look/dress a certain way to fit that part.0
Most Helpful Girl
It means America is turning into shit.
Our forefathers would be rolling in their graves.2