Possibly silly question about shoes

Hi Brooke!
I did a bunch of shopping this weekend. I want to dress a lot nicer now that I need new clothes and am no longer in plus sizes so that it is easier to find pretty items. I’m beginning to buy nicer clothes but feel that my shoes are still frumpy. I have not worn pretty heels in over 20 years and am now considering them again. However, I just cannot seem to wear them without my feet hurting. I bought a beautiful pair of high heel boots that were hurting my feet in just a couple of hours. The whole time I watched your How To Feel Better videos, I was thinking “How does she stand in those shoes all day!” Seriously, what is the secret to being able to wear heels comfortably? Even expensive ones make my feet hurt. (Of course I have never tried extremely expensive ones.) Is it a matter of needing to have all my excess weight off or I just need to try a more expensive brand or just suck it up and deal with the discomfort until you get used to it?