Usually means: Hat metaphorically worn for thinking.
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We found 11 dictionaries that define the word thinking cap:

General (11 matching dictionaries)
  1. thinking cap: Merriam-Webster
  2. thinking cap: American Heritage Dictionary of the English Language
  3. thinking cap: Collins English Dictionary
  4. thinking cap: Vocabulary.com
  5. thinking cap: Wiktionary
  6. thinking cap: Infoplease Dictionary
  7. thinking cap: Dictionary.com
  8. thinking cap: Rhymezone
  9. thinking cap: FreeDictionary.org
  10. thinking cap: Mnemonic Dictionary
  11. thinking cap: TheFreeDictionary.com

(Note: See thinking_caps as well.)

Definitions from Wiktionary (thinking cap)

noun:  (humorous) A metaphorical piece of headgear supposedly worn by a person to assist them in thinking about how to solve a problem.

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