I think I have more pairs of footwear than my wife, but the main ones for outdoors stuff are -
Karrimor KSB300 e-vent (also got a pair of GTX ones as 'spares', they were on sale..) for general walking round country parks, llight hiking etc
Old british army leather assault boots for muddy / bushcrafty stuff as they're cheap and tough, really comfy with Uvex gel insoles from a pair of steel toed boots in them
Le Chameau Mouflon plus (knee high leather and goretex) for walking about in autumn/winter and hunting. Lovely toasty feet in these, keep ticks etc off your lower legs.
I have a preference for boots which come up my shin a bit (ie 10 eyelet pairs) as I've broken my ankle before and the muscle has never really caught up with the other leg so the extra support is welcome.