Winsome/ˈwɪnsəm/ Definition 1 of 1Pro Tip 1/3Positive Connotation Winsome usually implies an innocent or naive charm that is endearing. The child's winsome expression melted the audience's hearts. Pro Tip 2/3Not Overwhelming Winsome charm is gentle and subtle, not excessive or overbearing. His winsome manner made him well-liked at work. Pro Tip 3/3Culturally Positive In English-speaking cultures, being described as 'winsome' is usually a compliment. She received the award with a winsome grace.