1. Charming, especially because of a naive, innocent quality: The pale blue dress that Lorna's friend wore was appropriate for her winsome personality.
2. Charming, often in a childlike or naive way; that is, having or showing an excessively simple and trusting view of the world and human nature, often as a result of being very young and inexperienced: The students joined in a winsome pose for the photographer at their summer picnic.
3. Etymology: winsome people easily "win" friends, so it should not be surprising that "winsome" and "win" have a common root.