Brewer's: Penny

(in the sense of pound). Sixpenny, eightpenny, and tenpenny nails are nails of three sizes. A thousand of the first will weigh six pounds; of the second, eight pounds; of the third, ten pounds.

Penny

sometimes expresses the duodecimal part, as tenpenny and elevenpenny silver- meaning silver 10-12ths and 11-12ths fine.

“One was to be tenpenny, another eleven, another sterling silver.” —Weidenfeld: Secrets of the Adepts.

Penny

(A) (Anglo-Saxon, penning or penig). For many hundred years the unit of money currency, hence pening-moncgre (a money-changer). There were two coins so named, one called the greater = the fifth part of a shilling, and the other called the less = the 12th part of a shilling.

My penny of observation

(Love's Labour's Lost, iii. 1). My pennyworth of wit; my natural observation or mother-wit. Probably there is some pun or confusion between penetration and “penny of observation” or “penn'orth of wit.”

A penny for your thoughts.

See Heywood's Dialogue, pt. ii. 4. (See Pennyworth.)

Source: Dictionary of Phrase and Fable, E. Cobham Brewer, 1894

Penny-a-liner

Penniless