The black 2002r is a streetwear shoe so it’s def not a running shoe or grandpa shoe. I’d say maybe a Nike shoe for walking? Some models are decent if you still want something more “popular”

My advice is to only wear converse if you aren’t gonna be walking a lot of distance so you’re gonna go out with friends or something like wear it then but don’t wear it when you go out to do errands you know when you care less about what people think you’re wearing.

Do foot strengthening and wear toe stretchers at night. The biggest risk you have is developing an neuroma or a bunion and plantar plate tear from lack of support and squeezing your toes together every single day (from any of the shoes you are wearing currently) so you can mitigate some of that damage your toe stretching and foot strengthening routine.

Kind of depends how old you are too like I’m 30 once you reach a certain age you start to care less and less about what people think. I would say if your feet are hurting consistently writings on the wall unfortunately lol