'winsome' originates from Old English, specifically the word 'winsum', where the root 'wynn/winn' meant 'joy, pleasure' and the suffix '-sum' meant 'characterized by'.

'winsome' changed from the Old English word 'winsum' (also attested in Middle English as 'winsome') and eventually became the modern English form 'winsome'.

Initially it meant 'pleasing, agreeable', and over time it retained and narrowed toward the sense 'charmingly attractive' used today.