I have an incredibly high arch and really require shoes that have arch support or the plantar fascia get inflamed. Many of my shoes have had the insoles ripped out and replaced with orthotics that increase the arch support. Wearing arch support has helped with my recovery from plantar fascitis and now I do wear some cute fashion-y shoes periodically at times when I know I will not be walking or standing for long periods of time.
My summer sandles are Mephisto Helen which feel like orthotics on my feet and I pretty much wear them every day for the day-to-day running around I do. I have little stick-on arch supprts that I put in to help hold up my arch. Not the best but help out enough that I don't have to spend the next couple days in bed.
In terms of higher heels, I must be very careful...too high and my inflamation flares. I also make sure that when I wear high heels, they have the "bend" hit a certain place in my foot so it acts like an orthotic of sorts.
Overall, the experience has been miserable for me. I love shoes and used to wear all the latest shoes all the time. Having to wear my "healthy" sandles every day has not been easy on my psyche. And there are very few "healthy" shoes that are actually cute and fashionable. And imagine me at a shoes store, testing every pair to see if I can rip out the insole and fit in my orthotic!
I have not yet resorted to Crocs. I doubt I ever will. Even my fussy feet have their limits.