You are Queen Purgatory!! It's one thing to purge the things that give you no joy. It's another thing entirely to purge things that you love...at least in theory!
Still, you're absolutely right to get rid of the shoes that hurt. I am going to join you on this mission. I have made a bit of a discovery this summer. My normally relatively unfussy feet have become much fussier after the serious beating I gave them hiking in the mountains in May.
I don't know what exactly went wrong with the trail runners I was wearing. I have worn them for several years in similar circumstances and I've never had a problem with them . But this year, they literally tore my right foot to shreds and made every other shoe uncomfortable, too. And still I wore the darn things! (Sometimes I'm thick like that. I lost a toenail to this stubbornness, with two more looking precarious. And my foot has yet to fully recover.)
Then, on my recent weekend trip, I wore a pair of Sam Edelman Suttons from last year and it seems I walked one mile too many in them in the heat . I'm now paying with some major blisters. Fortunately those are not in the same places as the trail runner blisters and callouses. Even more fortunately, I'd brought several changes of shoes so I did not have to wear the offenders for the next few days. After that experience, I am seriously considering tossing these sandals, despite the fact that they fill a major footwear hole for me.
The difficulty for me -- maybe for you, too -- maybe for most of us? -- is finding shoes that truly ARE as comfortable as they seem to be in the store! And that also fill those wardrobe needs.
I am not surprised that the shoes you mention are going out -- they wouldn't work for me, either -- any shoe that makes me "grip" makes my foot so very tired.
It is really sad about the Okalas but I also understand this impulse. I have actually managed to wear mine enough to make them a barely acceptable expense (having purchased them on sale) but they are hardly an every day shoe. For me, they're a four month a year dressy sandal substitute. And if I'd paid full price, I think I'd be feeling a lot more guilty now.
Worse are my bronze Donald Pliner booties from last year's NAS. I knew I wouldn't wear them often, and told Sveta as much when we were discussing their purchase. She, who normally takes a stiff line, was enabling, while I was expressing doubts. Well, turns out I was right about the doubts. I'm not sorry I bought them -- I did wear them for my stepson's wedding and a few other big occasions for which I would not otherwise have had appropriate footwear. But truly? They're just taking up space in the closet. The occasions for wearing them are far too few, and if my wardrobe were as tightly curated as yours, I would have to eject them to make room for something more practical.
My own lesson about this is that the narrow heel, even if comfortable, simply feels too dressy and too "forced" for my usual environment. It's not practical for walking on uneven sidewalks. So I end up rejecting the shoe even when I love how it looks with an outfit.
As for your pants...that is absolutely, 100% understandable to me, also. You need items that can do triple and quadruple duty, not items that scream, "ME ME ME!!!" every time you wear them.