winsome

adjective

win·​some ˈwin(t)-səm 

1

: generally pleasing and engaging often because of a childlike charm and innocence

a winsome smile

2

: cheerful, lighthearted

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.

Synonyms

• cheerful
• bright
• optimistic

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

But the voice shining through all this miming is the winsome, only moderately wicked one of Butts, who has for years been a cult favorite among fans of traditional country. —Chris Willman, Variety, 24 July 2025

Jellies—the name alone evokes the winsome wobbliness of childhood—are the closest thing to footwear candy: bright-colored, low-cost, empty-caloried. —Jillian Steinhauer, New Yorker, 27 June 2025

All three movies are packed with dinosaurs—dinosaurs running, dinosaurs being sad and winsome, dinosaurs showing ruthless disregard for human life. —Stephanie Zacharek, Time, 30 June 2025

Among the returning favorites is Reece Weaver, a winsome rookie candidate who became a main character in Season 1. —Angelique Jackson, Variety, 4 June 2025

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

before the 12th century, in the meaning defined at sense 1

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Kids Definition

winsome

adjective

win·​some ˈwin(t)-səm 

1

: having a charming or pleasing quality

a winsome smile

2

: cheerful sense 1a

a winsome mood

winsomely adverb

winsomeness noun