UK, 1882—‘penny’ refers to inexpensiveness, and ‘puzzle’ to the mysterious nature of the ingredients—perhaps also in humorous allusion to ‘penny puzzle’ in the sense of a puzzle-card sold on the street for one penny
also ‘in a wad’, ‘in a knot’, etc.—to become unduly agitated or angry—the plural noun ‘panties’ refers to short underpants worn by women or girls—American English, 1975
one who rides a surfboard with the right foot forward instead of the left—USA, 1960 (as a verb)—here, ‘goofy’ seems to be related to prejudice against left-handedness and left-footedness
the style of language considered characteristic of crossword clues or solutions—USA, 1925—from the noun ‘crossword’ and the suffix ‘-ese’, forming nouns designating the style of language considered characteristic of the first element
a game in which players must obey a leader’s instructions if, but only if, they are prefaced with the words ‘O’Grady says’—UK, 1917—game invented during World War One as a play-way for conducting physical exercises and drill in the British Army
1910: a cheap and common watch—hence (from 1922 onwards) used in various phrases referring to silliness, reliability/unreliability, erraticism, cheapness, funniness
Australia, 1970—as a noun and as a verb, refers to a high-speed drive in a motor vehicle—from the surname of the Argentinian motor-racing driver Juan Manuel Fangio