'vintage-looking' originates from modern English compounding of the adjective 'vintage' and the present participle 'looking'. 'Vintage' in English ultimately comes from Old French 'vendage' (later 'vintage'), which itself derives from Latin 'vindemia' ('vin-' related to 'wine' and '-demia' to 'harvest'). 'Looking' derives from the verb 'look' (Old English roots), meaning 'to have the appearance of.'

'vintage' changed from Latin 'vindemia' (grape harvest) through Old French 'vendage'/'vintage' into Middle/Modern English where its sense broadened from a wine harvest to the idea of an earlier year or era and items of notable age or quality. The compound 'vintage-looking' is a modern English formation combining that sense of 'from an earlier era' with 'looking' (the present participle of 'look') to indicate appearance.

Initially, 'vintage' referred specifically to the grape harvest (wine production). Over time it shifted to mean 'of a particular year or past era' and then to describe items that are characteristic of or evocative of the past; 'vintage-looking' now means 'having an appearance that evokes a past era.'