Usually means: Wearing insufficient clothing for occasion.
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We found 14 dictionaries that define the word underdress:

General (14 matching dictionaries)
  1. underdress: Merriam-Webster
  2. underdress: Oxford Learner's Dictionaries
  3. underdress: American Heritage Dictionary of the English Language
  4. underdress: Collins English Dictionary
  5. underdress: Vocabulary.com
  6. underdress: Wordnik
  7. underdress: Wiktionary
  8. underdress: Webster's New World College Dictionary, 4th Ed.
  9. underdress: Infoplease Dictionary
  10. underdress: Dictionary.com
  11. underdress: Rhymezone
  12. underdress: FreeDictionary.org
  13. underdress: Mnemonic Dictionary
  14. underdress: TheFreeDictionary.com

(Note: See underdressing as well.)

Definitions from Wiktionary (underdress)

verb:  (transitive, intransitive) To dress in insufficiently warm clothes.
verb:  (transitive, intransitive) To dress in insufficiently formal clothes.
noun:  (countable) Any dress (feminine-style garment) worn under another, especially under an overdress.
noun:  (countable, uncountable) Any garment (any clothing) that is worn under another but is not underwear.

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