Weekends and yardwork: Heavy winter boots, hiking boots, running shoes, faux-Converse in black and another pair in brown. Soon to acquire some work boots.
Dress (balmoral, leather sole): Black leather dress shoes (cap toe). Brown leather dress shoes (perf cap toe).
Workday (derby, rubber sole): Brown leather dress boots (perf cap toe). Brown leather (plain toe). Soon to acquire a pair of black leather dress boots.
Specialty: sandals, climbing shoes, MTB shoes, crocs.
That's thirteen and I still don't feel like all my bases are covered -- I'd like a nice pair of black patent balmorals for the dozen times a year I've got to be in a tuxedo.
I'm backwardly fortunate that my feet are obscenely long and narrow. It's easier to justify not buying shoes when they simply don't exist in US 14AA.