Winsome describes people and things that are cheerful, pleasant, and appealing.

// Though a relative newcomer to acting, Maya won the casting directors over with her winsome charm, which was perfect for the role of the plucky young superhero.

// Our winsome guide put us at ease immediately.

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“Wilson’s take on Snow White is surprisingly winsome. It delivers a familiar story with a fresh perspective and some unexpected sources of nostalgia.” — Kristy Puchko, Mashable, 19 March 2025

Despite appearances, winsome bears no relation to the familiar word win, meaning “to achieve victory.” The Old English predecessor of winsome is wynsum, which in turn comes from the noun wynn, meaning “joy” or “pleasure.” And the ancestor of win is the Old English verb winnan, meaning “to labor or strive.” Given those facts, one might guess that the adjective winning, meaning “tending to please or delight,” as in “a winning personality,” is a winsome relation, but in fact it’s in the win/winnan lineage. Winning is more common today than the similar winsome in such constructions as “a winning/winsome smile,” but we sense no hard feelings between the two. It’s just the way things (lexically) go: you win some, you lose some.