I’ve checked the SDMB database and I’ve not seen this one answered, so I’ll toss it out. Where does this come from? I’ve never seen and explaintion for this phrase or why it’s suppose to be an insult.
I have my own hypothesis:
This phrase is old and goes waaaaaaay back before our Modern Military. So, a woman wearing boots obviously made for use in the army or military in general would be unusual. Why would a woman being wearing them?
Possible answer: they were given to her or stolen by her for “services rendered” ie: she’s a camp follower or prostitute and got the boots as payment for her services.
Therefore, saying that your mother wore army boots indicates she’s a prostitute. That’s a pretty good insult.
Alright, the logic’s convoluted, but I think it gets the point across. Anyone know the real reason?