winsome

1 of 2

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

winsomeness

2 of 2

noun

win·​some·​ness

plural -es

: the quality or state of being winsome

the calculating winsomeness of a man who is spoiled by the ladies

—Kenneth Roberts

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 of winsome

Adjective

• cheerful
• bright
• optimistic

Examples of winsome in a Sentence

Adjective

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

Adjective

Halle Bailey is winsome and sprightly as Anna, a once-aspiring chef now reduced to working as a house sitter for wealthy clients in New York. —Bilge Ebiri, Vulture, 10 Apr. 2026

At the kickoff of his Land of Hope & Dreams American Tour at the Target Center March 31, Springsteen and the mighty E Street Band delivered a purposeful show stocked with serious messages, but also winsome fan favorites. —Melissa Ruggieri, USA Today, 1 Apr. 2026

Madrazo also has great discernment in subtly arranging pictorial props, such as clothing, cards or flowers, that stage his winsome female figures to good effect. —Benjamin Lima special Contributor, Dallas Morning News, 18 Mar. 2026

Aham, however, is a less winsome figure. —Tyler Austin Harper, The Atlantic, 18 Mar. 2026

Word History

Etymology

Adjective

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

Adjective

1677, 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