Usually means: Confused, unclear, muddled thinking state.
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We found 8 dictionaries that define the word woolly-head:

General (8 matching dictionaries)
  1. woolly-head: Wordnik
  2. Woolly-head: Dictionary.com
  3. Woolly-head: Online Plain Text English Dictionary
  4. woolly-head: Webster's Revised Unabridged, 1913 Edition
  5. Woolly-head: AllWords.com Multi-Lingual Dictionary
  6. woolly-head: FreeDictionary.org
  7. Woolly-head: TheFreeDictionary.com
  8. woolly-head: Wiktionary

Definitions from Wiktionary (woolly-head)

noun:  A woolly-headed person, particularly (potentially offensive) a black or Arab with Afro-textured hair.
noun:  (historical US slang) Synonym of abolitionist: an activist or politician opposed to slavery.

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