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bootless (adj.1)

"lacking boots," late 14c., from boot (n.1) + -less.

bootless (adj.2)

"without advantage, unprofitable," late Old English botleas "unpardonable, not to be atoned for, without help or remedy," from boot (n.2) + -less. Meaning "useless, unprofitable" is from early 15c.

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Definitions of bootless from WordNet

bootless (adj.)
unproductive of success;
Synonyms: fruitless / futile / sleeveless / vain
From wordnet.princeton.edu