I think you have to know your feet and your needs and it sounds like you have done that. I tend to have what seems like too many shoes because on a lot of days, I need 14-hr + serious no-nonsense shoes and it just takes Clarks loafer/shootie style or laceup or something to do that, but I have a range for different pants--almost just as you say with these. In other words, I aim for the least-frumpy version of frumpy so I have several types and heel heights. Elsewise I would just have to wear track shoes or hiking shoe.
Strategy also is, with my fussy feet, if I wear shoes most of the time that don't squish my toes or make bunion worse or whatever, I find I can continue to wear other more fashion-forward shoes from time to time, such as certain flats for office desk work days, heels (somewhat) for special occasions, more pointy-toe if it works with a specific outfit, and the like.
Walk a mile in another lady's feet before you jump to criticizing her footwear fashions! There may be a strategy at work and not just fashion-ignorance.