instead of brands, look for heels that are wedges, have a platform, or are kitten heels. Those are going to be more comfortable than something like a stiletto.

This takes practice and depends a lot on your foot shape but Naturalizer are usually good, and some are good looking.

I've never had a high heel break though, how in the world are you walking that's breaking them?

I have a slightly niche need for a high heel that I can stand still in for a while. I found that, for my feet at least, if I wear flats, my heels hurt; if I wear high heels over a certain height, the balls of my feet hurt. The sweet spot for me is a heel of 1.5 inches (sorry for the freedom units). The ones I ended up getting and liking (after trying a few) were the brand Cobb Hill. They ran me slightly over $100, so I didn’t love that part, but they have a nice solid heel that I didn’t find so square that it was ugly, and they’re relatively comfy. I can’t say that after wearing them for three hours, mostly standing still, that my feet don’t hurt, but they hurt a loooot less than anything else I’ve tried.

Aqua Italia makes some good patent leather pieces. Mephisto best for walking, they have some boots with a heel.