Wide boy

Conjures up images of London working class youth, living on the borders of criminality and, indeed, this meaning is first attested for this phrase from the 1950s. On digging a little deeper, the OED has the word ‘wide’ as colloquial or slang and meaning, ‘going beyond bounds of restraint, propriety, or virtue; loose, immoral’ and dates this usage and meaning from as far back as 1574. Wide boys, therefore, might have been around for a long time before the 1950s.