Definitions

from The American Heritage® Dictionary of the English Language, 5th Edition.

  • adjective Taking insufficient care; negligent.
  • adjective Marked by or resulting from lack of forethought or thoroughness.
  • adjective Showing a lack of consideration.
  • adjective Unconcerned or indifferent; heedless.
  • adjective Unstudied or effortless.
  • adjective Exhibiting a disposition that is free from cares; cheerful.

from The Century Dictionary.

  • Free from care or anxiety; hence, undisturbed; cheerful.
  • Giving no care; heedless; negligent; unthinking; inattentive; regardless; unmindful.
  • Done or said without care; unconsidered: as, a careless act; a careless expression.
  • Not receiving care; uncared for.
  • Synonyms and Supine, Indolent, etc. (see listless); incautious, thoughtless, remiss, forgetful, inconsiderate.

from the GNU version of the Collaborative International Dictionary of English.

  • adjective Free from care or anxiety. hence, cheerful; light-hearted.
  • adjective Having no care; not taking ordinary or proper care; negligent; unconcerned; heedless; inattentive; unmindful; regardless.
  • adjective Without thought or purpose; without due care; without attention to rule or system; unstudied; inconsiderate; spontaneous; rash.
  • adjective rare Not receiving care; uncared for.

from WordNet 3.0 Copyright 2006 by Princeton University. All rights reserved.

  • adjective marked by lack of attention or consideration or forethought or thoroughness; not careful
  • adjective effortless and unstudied
  • adjective (usually followed by `of') without due thought or consideration

Etymologies

from Wiktionary, Creative Commons Attribution/Share-Alike License

From Middle English careles, from Old English carlēas ("careless, reckless, void of care, free from care, free"), equivalent to care +‎ -less.

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