If you put glasses case in with all of that, it might get too stuffed, but you can try. I used to own Mini Mini and it was both a great small crossbody, and a bag organiser in bigger bags and totes.
A Mini would fit all you mentioned but is bigger hence rounder, sticks out more from your body.. I own the large size now and like it but it does stick out
I don't know the Cloud. For everyday I'd go with Mini so your glasses can fit and it's still lightweight. But I haven't tried cloud. I feel like your glasses case either would stick out of mini mini, or fall out of it too easily