1
: turned or tilted to one side : askew
a cockeyed hat
He had brown curly hair, and a little cockeyed grin that made girls and women smile back.—
Tracy Kidder
Tracy KidderIn the narrow streets between are steep-roofed Renaissance houses with sculpted beams, cockeyed walls, and old wells.—R. W. Apple, Jr.
R. W. Apple, Jr.2
: somewhat confusing, foolish, absurd, or impractical
a cockeyed scheme/idea
Call me a peacenik, a cockeyed optimist, a technology fanboy—I've been called worse—but I see the opportunity in engaging, in negotiating, and in connecting these cultures …—Jeff Jarvis
Jeff JarvisA mondegreen is a cockeyed new word or phrase resulting from mishearing a proper word or phrase …—Rudolph Chelminski
Rudolph Chelminski
also
: in utter confusion or disorder : topsy-turvy
Bruce Catton called it "a startling novel about the horrible things that can happen to a man in the cockeyed postwar world of Europe … a world gone mad." —John Anthony West
John Anthony West 3
: having a cockeye
4
: drunk sense 1a
… gets wonderfully cockeyed in the neighborhood bar with her old friends.—Jane Cobb
Jane CobbExamples of cockeyed in a Sentence
The windows of the house look cockeyed.
Where did you get those cockeyed ideas?
She is full of cockeyed optimism.
Recent Examples on the Web
The Trump Administration, through some cockeyed revision of the Monroe Doctrine, seems eager to stake a claim to the entire Western Hemisphere.
—Jay Caspian Kang, New Yorker, 13 Jan. 2026
But even to the cockeyed optimist, did six sacks feel plausible Sunday night?
—Andrew Callahan, Boston Herald, 12 Jan. 2026
Gunn the cockeyed empathetic optimist didn’t make his public debut until the first Guardians of the Galaxy.
—Matt Zoller Seitz, Vulture, 31 Oct. 2025
But then come the passages of cockeyed brilliance—such as this one, yoking Nicholas’s philosophical meditation on the nature of subjective perception to the 1960s sitcom Gilligan’s Island.
—Scott Stossel, The Atlantic, 9 Sep. 2025
See All Example Sentences for cockeyed
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Jay Caspian Kang, New Yorker, 13 Jan. 2026
But even to the cockeyed optimist, did six sacks feel plausible Sunday night?
—Andrew Callahan, Boston Herald, 12 Jan. 2026
Gunn the cockeyed empathetic optimist didn’t make his public debut until the first Guardians of the Galaxy.
—Matt Zoller Seitz, Vulture, 31 Oct. 2025
But then come the passages of cockeyed brilliance—such as this one, yoking Nicholas’s philosophical meditation on the nature of subjective perception to the 1960s sitcom Gilligan’s Island.
—Scott Stossel, The Atlantic, 9 Sep. 2025
See All Example Sentences for cockeyed
Cite this Entry
“Cockeyed.” Merriam-Webster.com Dictionary, Merriam-Webster, https://www.merriam-webster.com/dictionary/cockeyed. Accessed 30 Jan. 2026.
Copy CitationKids Definition
cockeyed
adjective
cock·eyed
ˈkäk-ˈīd 
1
: having a squinting eye
2
: turned or tilted to one side
3
: somewhat confusing, foolish, absurd, or impractical
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