If your heels hurt, the problem is probably your arches (either high or flat footed). Barefoot shoes or orthotics are two competing solutions to choose from.

Barefoot shoes have thin, flexible soles, minimal cushion, no arch support, and wide toe boxes. The premise is that strengthening the weaker foot muscles (from wearing supportive shoes and heel lifts) will address pain by supporting your legs better.

Anya’s Reviews is great, I’d start here. Some people have found that transitioning improves pain from traditional shoes (that’s why I switched).

Otherwise if you don’t want to go the barefoot route, you can get a pair of custom orthotics made that will probably last for life (pretty pricey).

If your issue is comfort then you may need to sacrifice durability. Orthotics are more likely to be BIFL in that they can last a very very very long time (basically just molded plastic). Barefoot shoes are not BIFL, but the route is BIFL in that sense that it encourages using your own anatomy for walking, which can help your knees and hips in the long run.

Pro for orthotics is that they can go in any shoe. But pro for barefoot shoes is that even dress styles will feel like loungewear.