Usually means: Effortless style, charisma, and appeal.
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We found 25 dictionaries that define the word coolness:

General (20 matching dictionaries)
  1. coolness: Merriam-Webster
  2. coolness: Oxford Learner's Dictionaries
  3. coolness: Collins English Dictionary
  4. coolness: Vocabulary.com
  5. Coolness, coolness: Wordnik
  6. coolness: Cambridge Advanced Learner's Dictionary
  7. coolness: Wiktionary
  8. Coolness, coolness: Dictionary.com
  9. coolness: Cambridge Essential American English Dictionary
  10. Coolness: Wikipedia, the Free Encyclopedia
  11. Coolness: Online Plain Text English Dictionary
  12. coolness: Webster's Revised Unabridged, 1913 Edition
  13. coolness: Rhymezone
  14. Coolness: AllWords.com Multi-Lingual Dictionary
  15. coolness: Webster's 1828 Dictionary
  16. coolness: FreeDictionary.org
  17. coolness: Mnemonic Dictionary
  18. coolness: TheFreeDictionary.com

Business (1 matching dictionary)
  1. coolness: Legal dictionary

Computing (1 matching dictionary)
  1. coolness: Encyclopedia

Miscellaneous (1 matching dictionary)
  1. coolness: Idioms

Slang (2 matching dictionaries)
  1. coolness: Green’s Dictionary of Slang
  2. Coolness, The Coolness: Urban Dictionary

(Note: See cool as well.)

Definitions from Wiktionary (coolness)

noun:  (uncountable) The state of being cool, i.e. chilly.
noun:  (countable) The result or product of being cool, i.e. chilly.
noun:  (uncountable) The state of being cool, i.e. calm.
noun:  Indifference; lack of friendliness or interest.
noun:  (slang, uncountable) The state of being cool, i.e. good or pleasing.
noun:  (slang, countable) The result or product of being cool, i.e. good or pleasing.

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