Usually means: Tight, uncomfortable, old-fashioned expression origin.
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We found 6 dictionaries that define the word Dick's hatband:

General (5 matching dictionaries)
  1. Dick's hatband: Wiktionary
  2. DICK'S HATBAND: Dictionary of Americanisms (1848)
  3. Dicks Hatband: The Word Detective
  4. Dick's hatband: World Wide Words
  5. Dicks Hatband: Dictionary of Phrase and Fable (1898)

Slang (1 matching dictionary)
  1. dick's hatband: Urban Dictionary

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Definitions from Wiktionary (Dick's hatband)

▸ noun:  (colloquial, now principally US, dated) Used in similes as an intensifier, indicating someone or something is extremely strange, tight, etc.


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