Without boots; or figuratively, unsuccessful, useless, or pointless; achieving nothing despite effort.
From 'boot' plus '-less' suffix meaning 'without' or 'lacking'; the figurative meaning derives from Old English 'bōt' (advantage or remedy), making 'bootless' mean 'without benefit' or 'to no avail'.
The figurative meaning of 'bootless' (useless) comes from Old English 'bōt' meaning remedy or advantage—King Lear uses 'bootless' to describe tears that provide no remedy, showing Shakespeare understood this ancient word meant 'without redemption.'
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