"A person or action which can be described by the [Greek] word kalos is not only good; he or it is also beautiful. It therefore has in it the idea of goodness which is winsome and attractive. Very often the best translation of it is 'lovely'" (William Barclay).
WINSOMENESS IS ONE KIND OF GOODNESS: IT'S THE KIND OF GOODNESS THAT IS "ATTRACTIVE." When someone is charming or delightful, we're attracted to them. We're pulled toward them. The pull is not a physical force like gravitation or magnetism, yet it sometimes feels that compelling. (Antonyms like "repulsive" or "repellent" share the same metaphor, of course, only in reverse. People with these qualities push us away from them.) "Winsomeness," then, is attractive goodness, goodness that pulls with the power of likability.
In ancient times, the Greeks had a special word for this kind of goodness: kalos. In contrast to agathos, the normal word for "good," kalos meant that which was fine or admirable or praiseworthy. If something was kalos, it was not only right and correct from a technical viewpoint, but it was also delightful. And these are two very different kinds of goodness, aren't they? We all know people who are scrupulously correct, but their rightness doesn't have much warmth or beauty to it. We know others who are no less concerned to do the right thing, but their goodness is also lovely and inviting. They are winsome.
It's interesting that our English word "winsome" comes from the Old English wynn, which simply meant "joy." When we say that a friend has a "winning" smile, we don't just mean that their facial expressions can win us over but that their goodness gives us great joy.
Are you working on your winsomeness? I hope so. And I hope you'll see it as something more than just a personality trait. In reality, it's a character trait. Real winsomeness has a much higher goal than "how to win friends and influence people." It's not a technique to use, but a gift to give. It's the imparting of daily grace to those around us.
A sweet attractive kind of grace,
A full assurance given by looks,
Continual comfort in a face,
The lineaments of Gospel books;
I trow that countenance cannot lie
Where thoughts are legible in the eye.