i too have worn the "cowboy" type boot for 40+ years.
just bought some alpinestar gortex all weather boots and am having trouble shifting with them.
may be beacause they are still stiff, but it seems that the foot and sole part are much thicker than my old boots making it difficult to fit my toe under the shifter.
i have adjusted the shifter to the max up and will see if that works.
next is to move the shifter one spline and see how that is if the above does not work. think i will just keep adjusting up untill it fits right.
if i get it high enough for upshifts i may need to lift my foot too far off the peg for downshifts. in that case i will have one pair of alpinstars for sale cheap.
a friend had his scuba gear stolen so he replaced it with pink stuff. never had it stolen since. because the thief would be easy to spot,,,,or?????
UPDATE: just gave it a try after adjustment and all is fine now. may even be a little too high but i'll leave it for now