check·​ered ˈche-kərd How to pronounce checkered (audio)
: marked by alternating squares of different colors, shades, or materials
a checkered fabric
checkered tablecloths
see also checkered flag
: marked by alternation or contrast of fortune
… the best album of his checkered careerMark Coleman
especially : marked by many problems or failures
… had a checkered past that included convictions for battery and tax evasion. 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 digital collection features a checkered suit, pixel leopard hoodie and video game pants — free of charge for fitting, sharing and saving to digital wardrobes within the ZERO10 app. Stephanie Hirschmiller, Forbes, 25 Aug. 2022 Each of them wore a checkered dog sweater with a hoodie in their size. Kimberlee Speakman, Peoplemag, 25 Dec. 2022 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 The checkered kicks are one of Cruz’s picks for the auction and are estimated to sell for between $150,000 and $200,000. Demetrius Simms, Robb Report, 23 Nov. 2022 Taking pictures on a boat with friends in Sydney, Dua wore a teeny, black and white checkered bra with a coordinating bottom. Abby Dupes, Seventeen, 10 Nov. 2022 On Wednesday, Mayor Michelle Wu introduced Michael Cox, now 57, as the city’s next police commissioner, surely the most extraordinary and improbable appointment in that department’s — or perhaps any police department’s — long and checkered history. Yvonne Abraham,, 13 July 2022 Directed by by John Rando, the musical now focuses on Buddy’s family as much as his checkered career, which spans from the Borscht Belt to the early days of television to gigs at senior centers. Frank Rizzo, Variety, 27 Apr. 2022 When searching for pieces, go for anything quilted, checkered and floral patterned, and try to find handmade glazed and ceramic dinnerware. Bryce Jones, Better Homes & Gardens, 6 Nov. 2022 See More

These examples are programmatically compiled from various online sources to illustrate current usage of the word 'checkered.' Any opinions expressed in the examples do not represent those of Merriam-Webster or its editors. Send us feedback about these examples.

Word History

First Known Use

15th century, in the meaning defined at sense 1

Time Traveler
The first known use of checkered was in the 15th century

Dictionary Entries Near checkered

Cite this Entry

“Checkered.” Dictionary, Merriam-Webster, Accessed 24 Sep. 2023.

Kids Definition


: marked by changes of fortune
a checkered career
especially : marked by many problems
a checkered past
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