They are both really pretty! But I maybe see what you mean about the shape of the pair with the black heel- a bit sort of wide in the middle/shaft?
I could still wear my heeled booties in our winter but I don’t reach for them for work, so am only buying low heeled ones from now on ( I hope!- will try to stick to that!).

If whether I wore something or not during covid was criteria for purging I'd have nothing left in my closet! I did a big shoe purge in 2019, culling all but the most comfortable. I wish I could say I have not purchased new shoes during covid, but I duped a pair of La Canadienne booties, got a pair of warm suede ankle booties for neighborhood walks with the dog, and a pair of higher shaft (not ankle, but not even mid calf) lace up booties to wear 90's style with longer skirts. I have not donned a skirt... in all of 2020 and into 2021 haha. I am sad that much of my wardrobe sits languishing, but when we get back to normal most of it won't look dated or anything.

I like the booties on the left however, and would def keep those.

Wow, lots of similar “keep” advice here, which I would echo. My comment mostly has to do with anything, especially footwear, looking dated after Covid is gone. In my mind, the months of covid quarantine/seclusion/lockdown/distancing/activity lack appear like a big fold or pleat in time, and we will find that we’ve stepped over it as if on a bridge to the future, and it will be the same as when we left... weird, but hopeful? So fashion will not have moved on without us.

cjh - and others: I realize my comment about footwear looking dated once post-covid activity resumes was not well-articulated. I agree - and hope that- this will be a "pleat" (love that) in time that won't all of a sudden make our wardrobes look out of place. Any footwear I'm looking at to donate I haven't missed wearing at all.

I love footwear as much as anyone, but this past year has shown me that having a huge variety of colour isn't important to me and that at the end of the day, having a variety of styles in maybe 3 different colours/textures is all I need. Depth, vs breadth, as it were.

I did a shoe edit recently of anything that hurt my feet, which included mostly high heels. I now need to look at my sandals . I have absolutely loads of them and they all seem uncomfortable . I have a problem with my left foot sole that comes and goes. I keep holding onto them in the hope that things will really improve, heaven knows why as I don't even like half of them but I cannot for the life of me find ones that I like and don't hurt. More chance of finding a unicorn lol.
Both the pairs you show Lisa look stylish to me especially the perforated pair.

I hear you on not wanting to lounge in pjs & sweats all day, every day. And we all know I’m not into purging for it’s own sake. But you stopped wearing these in 2019 before most of us had even heard of Corona, so I’d say find them a new home and when you get more, make sure they will have longevity in your closet.