What shoes? What occasion? General tips?

hi i feel like neither of the shoes really fit? (the left ones are boots btw)

also is this even a cute fit? it seems like somethings weird GIVE ME ALL YOUR OPINIONS PLEASE :)))

i've been watching the show 'friends' and they look so chic and classy! thats why i tried something new and now im clueless when and where i should wear this? i feel so insecure and extra... also pls be brutally honest thank uu