'tired-looking' originates from English, composed of 'tired' (the past participle of 'tire') and 'looking' (the present participle of 'look'). 'tire' comes via Middle English from Old French 'tirer', where 'tirer' originally meant 'to pull' (sense later extended toward causing weariness), and 'look' comes from Old English 'lōcian', where 'lōcian' meant 'to look'.

'tire' developed in Middle English as 'tirien' meaning 'to grow weary', producing the past participle 'tired'; 'look' comes from Old English 'lōcian' and evolved into Modern English 'look'; the compound adjective 'tired-looking' arose in Modern English by combining the participial form 'tired' with 'looking' to describe appearance.

Initially 'tired' referred to having been made weary; over time the compound 'tired-looking' came to specifically describe appearance—i.e., 'having the appearance of being tired'—rather than the internal state itself.