So, I think you are actually mourning your pre-COVID life, when you had opportunities to wear the kinds of clothes you enjoy shopping for. No wonder it's hard now!
I understand this. When I lived in a miserable winter climate, I loathed shopping for winter parkas, practical snow boots, and basically, for any item that was impractical to wear for 6 months a year in my climate. I loved shopping for blazers, skirts (to wear without hose), sandals, light summer dresses or tops -- all the stuff I rarely got to wear!
My situation is a bit different now, in that I live in a more temperate climate so theoretically, I don't need to shop for all that boring stuff I dislike. Yay!!
But COVID has definitely cramped my style. There is simply no reason to shop for dressy items, since I will not be wearing them, full stop. I don't enjoy dressing as casually as I feel I need to, now, but if I'm going to be clothed and feel good about my at-home style, I'll have to get used to shopping for more comfortable, casual things.
Either I'll come up with a work-from-home uniform of sorts, the way Jenn does, or I'll find some really luxe loungewear, or...I don't know, maybe both. I'm considering a really great pair of overalls for the hours I spend in the garden, for example. I'm trying to reframe "fashion fun" as what will prove useful to me in my actual life.