Usually means: Lacking boots; absence of footwear.
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We found 6 dictionaries that define the word bootlessness:

General (6 matching dictionaries)
  1. bootlessness: Merriam-Webster
  2. bootlessness: Collins English Dictionary
  3. bootlessness: Wordnik
  4. bootlessness: Wiktionary
  5. bootlessness: Dictionary.com
  6. bootlessness: FreeDictionary.org

(Note: See bootless as well.)

Definitions from Wiktionary (bootlessness)

noun:  (archaic) The quality of being unavailing or unprofitable.
noun:  The state of being bootless (without boots)

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