'Pretty' meant 'cunning, tricky' in Old English — it migrated through 'clever' to 'attractive' over five centuries.
Attractive in a delicate way without being truly beautiful or handsome; also used as an adverb meaning 'to a moderately high degree.'
From Middle English prety, praty (clever, skillful, fine), from Old English praettig (cunning, crafty, tricky), derived from praett (a trick, craft, wile), from Proto-Germanic *prattuz (trick, prank). The Proto-Germanic form may connect to PIE *pret- (to spread out, display), though the etymology is debated. The semantic journey is remarkable: Old English praettig meant "cunning, deceitful" — a praettig person was sly, not
Calling someone 'pretty' originally meant calling them 'tricky and deceitful.' Old English 'prættig' meant 'cunning, crafty,' from 'prætt' (a trick). The shift from 'sly' to 'attractive' took about 500 years. Dutch preserved a different positive sense: 'prettig' means 'pleasant, enjoyable, fun' — no visual beauty