The "literally/figuratively" glosses here are misleading, as though the second sense were a figurative application of the lack of boots (footwear). They aren't, I think, even the same etymology; the second might be related to (deprecated template usage) booty. Equinox ◑ 02:36, 18 July 2009 (UTC)
- To boot, I suspect the sense "pointless, to no avail" is from boot#Etymology 2. ~ Ningauble 16:00, 9 January 2010 (UTC)