I wondered about the feasibility of the pants and boots as well, but I'm not convinced its impossible. Besides, OWI have generally tried to keep the need to suspend disbelief to gameplay elements. I may be wrong, but I think they probably have diagrams somewhere of how Stranger's legs fit into those boots.
And speaking of diagrams, I'd really like to get some pics of Stranger from the operation pamphlet. Those seemed quite cool.
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