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
The checkered reputation of fan behavior dates to the days of England’s worst episodes of hooliganism in the 1970s and 80s.
—ABC News, 24 Apr. 2026
His mother, 76-year-old Beth Burbank, is a longtime Quaker and came out to support the vigil, carrying a poster in hand and a checkered keffiyeh — a Middle Eastern scarf and a modern symbol of colonial resistance — around her neck.
—Laura Turbay, Chicago Tribune, 21 Mar. 2026
The space is full of playful contrasts—checkered wallpaper from Schumacher, a leopard-print carpet, and a whimsical Avalon rattan daybed by Serena & Lily.
—Amy Bradford, Architectural Digest, 21 Mar. 2026
Inside, checkered floors, an old-school jukebox, and wraparound booths add to the atmosphere.
—Tara Massouleh McCay, Southern Living, 14 Jan. 2026
See All Example Sentences for checkered
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ABC News, 24 Apr. 2026
His mother, 76-year-old Beth Burbank, is a longtime Quaker and came out to support the vigil, carrying a poster in hand and a checkered keffiyeh — a Middle Eastern scarf and a modern symbol of colonial resistance — around her neck.
—Laura Turbay, Chicago Tribune, 21 Mar. 2026
The space is full of playful contrasts—checkered wallpaper from Schumacher, a leopard-print carpet, and a whimsical Avalon rattan daybed by Serena & Lily.
—Amy Bradford, Architectural Digest, 21 Mar. 2026
Inside, checkered floors, an old-school jukebox, and wraparound booths add to the atmosphere.
—Tara Massouleh McCay, Southern Living, 14 Jan. 2026
See All Example Sentences for checkered
Cite this Entry
“Checkered.” Merriam-Webster.com Dictionary, Merriam-Webster, https://www.merriam-webster.com/dictionary/checkered. Accessed 1 May. 2026.
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