Synonyms of winsome
1
: generally pleasing and engaging often because of a childlike charm and innocence
a winsome smile
2
winsomely adverb
winsomeness noun

Did you know?

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.

Examples of winsome in a Sentence

He had a winsome, boyish smile. she was a bright, winsome gamine who could draw a smile out of anyone
Recent Examples on the Web
Examples are automatically compiled from online sources to show current usage. Read More Opinions expressed in the examples do not represent those of Merriam-Webster or its editors. Send us feedback.
On his latest, Young’s major-key meditations on love and alienation are as winsome as a bay breeze, if occasionally as insubstantial. — Linnie Greene, Pitchfork, 20 Oct. 2026 This winsome experience—socialism as socializing—has filled a gap left by the increasingly professionalized mainstream political parties. — Benjamin Wallace-Wells, New Yorker, 18 Oct. 2026 Nearly fifty years later, Impromptu (1991) retold the story as wry, knowing rom-com, this time with Judy Davis as the capering novelist and Hugh Grant as the winsome composer. — Kathryn Hughes, The New York Review of Books, 17 Oct. 2026 Colette, our winsome young narrator played by Sophia Anne Caruso, will soon go on to provide a bit of explanation that only makes things more confusing. — Jackson McHenry, Vulture, 16 Oct. 2026 See All Example Sentences for winsome

Word History

Etymology

Middle English winsum, from Old English wynsum, from wynn joy; akin to Old High German wunna joy, Latin venus desire — more at win

First Known Use

1677, in the meaning defined at sense 1

Time Traveler
The first known use of winsome was in 1677

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Cite this Entry

“Winsome.” Merriam-Webster.com Dictionary, Merriam-Webster, https://www.merriam-webster.com/dictionary/winsome. Accessed 27 Oct. 2026.

Kids Definition

winsome

adjective
1
: having a charming or pleasing quality
a winsome smile
2
: cheerful sense 1a
a winsome mood
winsomely adverb
winsomeness noun
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