SENTENCE USAGE: "That ol’ lady Humbolt is tight as Dick’s hatband; she lost her big toe to infection rather than paying Doc Mosby two dollars to remove a splinter."

From "Heavens to Betsy" by Charles Earle Funk (1955): The ‘Dick’ alluded to in this metaphor was Richard Cromwell, ‘Lord Protector’ of England for a few months, September 1658 to May 1659. He had been nominated by his father, the powerful Oliver Cromwell, to succeed him in this high office and was actually so proclaimed. But whereas the father had served, at least from the death of Charles I in 1649, as quasi-king of England, king in fact if not in name, Richard was, alas, not the man his father was. He was too amiable, thrust into a position of responsibility at a time of national crisis and he was unable to reconcile the various factions in the military and Parliament. He was shortly dismissed from office. The crown was the ‘hatband’ in the saying, which was deemed a ‘strange’ adornment for the head of one so briefly in the highest office and too ‘tight’ for him to have worn in safety.

According to Robert Hendrickson’s "Whistling Dixie, A Dictionary of Southern Expressions" "tight as Dick’s hatband" is primarily a Southern U.S. expression though the phrase actually originated in Great Britain as mentioned above. "Tight as Dick’s hatband" made the leap across the Atlantic and took up residence in the American South, where, the Cromwell saga being largely unknown, it was taken as a folk expression denoting extreme tightness or, sometimes, stinginess.