1. offensive slang An inclination or willingness for sexual promiscuity. The phrase alludes to the heels of a woman's shoes becoming rounded due to her frequently falling backward onto a bed. We were warned against having round heels for so long when we were younger that many young women developed genuine anxieties about sex. Most men his age are just interested in round heels when they start dating, not looking to form anything resembling a serious relationship.
2. A tendency to relent to pressure very easily and without protest. It seems like every major company these days has round heels whenever some social justice warrior demands that they change something about their brand to be more politically correct. We need a leader with a spine, not some pushover with round heels.
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.
Promiscuous. The image is that of a woman who is such a pushover that the heels of her shoes became rounded from her being pushed over backwards so frequently. The phrase was popular in men's dormitories and barracks until the sexual revolution changed attitudes. Other obsolescent phrases and expressions were “a scarlet woman,” “a woman of easy virtue,” “loose [or “low”] morals,” a “tramp.” On the other hand, men were applauded for being a “lady's man,” a “cocksman,” a “Romeo,” or a “Casanova,” all of which demonstrate which gender controlled the language.
Endangered Phrases by Steven D. Price Copyright © 2011 by Steven D. Price