Dressier shoe options for someone with a history of foot pain?

I'm currently relegated to ultra cushioned running shoes like Hokas, Tevas, Merrell, or a cupsole sneaker + orthotic, and always thick socks. Even then my feet ache after 2 hours of being on my feet. Struggling to put together good looks while my shoes hold me back. Hoping loafers might be possible if anyone has any you recommend trying. Love the look of a boot but most feel like walking on concrete.