Definitions

from The American Heritage® Dictionary of the English Language, 4th Edition

  • adj. Taking insufficient care; negligent: a careless housekeeper; careless proofreading.
  • adj. Marked by or resulting from lack of forethought or thoroughness: a careless mistake.
  • adj. Showing a lack of consideration: a careless remark.
  • adj. Unconcerned or indifferent; heedless: careless of the consequences.
  • adj. Unstudied or effortless: danced with careless grace.
  • adj. Exhibiting a disposition that is free from cares; cheerful: a careless grin; a careless wave of the hand.

from the GNU version of the Collaborative International Dictionary of English

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

from The Century Dictionary and Cyclopedia

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

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

Etymologies

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

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