Usually means: Wearing insufficiently formal attire socially.
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We found 5 dictionaries that define the word underdressing:

General (5 matching dictionaries)
  1. underdressing: Merriam-Webster
  2. underdressing: Vocabulary.com
  3. underdressing: Wiktionary
  4. underdressing: Dictionary.com
  5. underdressing: TheFreeDictionary.com

(Note: See underdress 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.
▸ Also see underdress


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