bootless (adj.1) Look up bootless at Dictionary.com
"lacking boots," late 14c., from boot (n.1) + -less.
bootless (adj.2) Look up bootless at Dictionary.com
"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.