careless (adj.)

Old English caru, cearu "sorrow, anxiety, grief," also "burdens of mind; serious mental attention," in late Old English also "concern, anxiety caused by apprehension of evil or the weight of many burdens," from Proto-Germanic *karō "lament; grief, care" (source also of Old Saxon kara "sorrow;" Old High German chara "wail, lament;" Gothic kara "sorrow, trouble, care;" German Karfreitag "Good Friday;" see care (v.)).

The meaning "charge, oversight, attention or heed with a view to safety or protection" is attested from c. 1400; this is the sense in care of in addressing (1840). The meaning "object or matter of concern" is from 1580s. To take care of "take in hand, do" is from 1580s; take care "be careful" also is from 1580s.

The primary sense is that of inward grief, and the word is not connected, either in sense or form, with L. cura, care, of which the primary sense is pains or trouble bestowed upon something. [Century Dictionary]

word-forming element meaning "lacking, cannot be, does not," from Old English -leas, from leas "free (from), devoid (of), false, feigned," from Proto-Germanic *lausaz (cognates: Dutch -loos, German -los "-less," Old Norse lauss "loose, free, vacant, dissolute," Middle Dutch los, German los "loose, free," Gothic laus "empty, vain"), from PIE root *leu- "to loosen, divide, cut apart." Related to loose and lease.