Don't know the origin of the expression "red hat, no drawers", but it was around in my mother's generation, when most people, both men and women wore hats. I was never allowed to wear a red hat, not even a knitted one.

Think it might have some connection with a red light indicating the house of ill-repute, and a red hat indicating a prostitute before they openly hung about on street corners. In the 50s and 60s, prostitutes wore anklets to advertise themselves to prosective clients, but nowadays anyone wears one.

Jean in Poole, Dorset, UK
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