1
: marked by alternating squares of different colors, shades, or materials
a checkered fabric
checkered tablecloths
see also checkered flag
2
: marked by alternation or contrast of fortune
… the best album of his checkered career—
Mark Coleman
Mark Coleman
especially
: marked by many problems or failures
… had a checkered past that included convictions for battery and tax evasion. —Charlotte Triggs et al.
Charlotte Triggs et al. Examples of checkered in a Sentence
He has had a checkered career with many ups and downs.
Recent Examples on the Web
His character, Mooney, wears checkered shirts and brown corduroy and drives a gold ’64 Chevy Nova.
—Anne Thompson, IndieWire, 5 Sep. 2025
Given McCaffrey's rather checkered medical history, there has been some legitimate concern surrounding the superstar playmaker heading into 2025, but Bleacher Report's Gary Davenport sees better days in McCaffrey's future.
—Matthew Schmidt, MSNBC Newsweek, 28 Aug. 2025
Demos wore a checkered suit, while Shahi donned a slinky metallic dress with a thigh-high slit and off-the-shoulder detailing.
—Katie Mannion, Peoplemag, 18 Mar. 2024
Another picture shows a toddler in a cerulean bonnet, popcorn top, and black and white checkered tights holding a fuchsia version.
—Liana Satenstein, Vogue, 8 Dec. 2022
See All Example Sentences for checkered
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.
Anne Thompson, IndieWire, 5 Sep. 2025
Given McCaffrey's rather checkered medical history, there has been some legitimate concern surrounding the superstar playmaker heading into 2025, but Bleacher Report's Gary Davenport sees better days in McCaffrey's future.
—Matthew Schmidt, MSNBC Newsweek, 28 Aug. 2025
Demos wore a checkered suit, while Shahi donned a slinky metallic dress with a thigh-high slit and off-the-shoulder detailing.
—Katie Mannion, Peoplemag, 18 Mar. 2024
Another picture shows a toddler in a cerulean bonnet, popcorn top, and black and white checkered tights holding a fuchsia version.
—Liana Satenstein, Vogue, 8 Dec. 2022
See All Example Sentences for checkered
Cite this Entry
“Checkered.” Merriam-Webster.com Dictionary, Merriam-Webster, https://www.merriam-webster.com/dictionary/checkered. Accessed 9 Sep. 2025.
Copy CitationLove words? Need even more definitions?
Merriam-Webster unabridged
Share