In Bible times, what kind of woman would go out in public without a head covering?
In the culture of that day, a woman who went out in public without a head covering was typically a prostitute. Such women deliberately removed the customary veil to flaunt themselves and advertise their profession; Paul dealt with the issue under those circumstances.
Les explains that in the culture of that day, women were accustomed to wearing a veil, so for a woman to be out in public with nothing over her head was highly unusual. The kind of woman who would usually flaunt herself in that way was the prostitute. Prostitutes would remove these coverings from their head to unveil their profession. Paul therefore says that a woman praying or prophesying with her head uncovered dishonors her head, as if she were shaven. Les notes that if a woman is not covered, she should be shorn or shaved, but if that is a shame, then she should be covered. He clarifies that this does not mean women today must wear a veil or hat in church; rather, Paul was dealing with the customs and mindset of that specific culture, and custom has changed how these things are interpreted today.