Tbh, I think you have to treat the pandemic a bit like a death, don't make any rash big decisions for at least a year as you're probably not in the right frame of mind right now. And, yes, contents of your wardrobe are totally big decisions in my book 
I also have a pair of Acne stars and no way am I getting rid of those until they die and fall apart they're very versatile IME, good with the whole rolled up hems this past winter and have definitely worn them with flares in the past and that works really well.
I don't have Bobbies but the other infamous wedge sneaker pair (can't remember the name now, also something with a B, Barrett?) and they do have their moments of disappearing and coming back again. I think you need to try to wear the Bobbies differently than previously to see if they have another application, I can actually see those working with the very poofy sleeved babydoll dresses you see everywhere (provided you like those, I'm very meh about them).
Tbh, you also have to accept that if you're no longer feeling temporary iconic items, other people aren't either, so they're unlikely to fund much newness.
Change of topic, perhaps I'm just being cantankerous but is anyone else annoyed with all the newness flitting into their inboxes? I'm finally craving some spring (white dresses and anything in a good green) but it's all twee frills, puffy sleeves, country lace, etc. I despise the whole cottagecore takeover, it's far too juvenile for me, great if you want to live out your studio Ghibli dreams at any age if you want, but I'm ready for some adulting again after this brief pandemic existence of a lethargic teen.