I hear you! Here’s a thread from a while back:
Shoes are a terrible problem, aren’t they? But it is so worth finding something that’s comfortable and which you don’t mind wearing. Unfortunately, what’s comfy for someone else might not suit your feet. And equally unfortunately, trial and error is the only way to find out.
I think I’d make an appointment with the podiatrist, and see whether, based on your problem areas, they can suggest what types/styles of shoe to look at. As for insoles, I wasted a lot of money on orthotics before a new podiatrist told me that the only orthotic i should consider is an accommodative type. That is, one which cushions and supports to lessen pain. She also suggested a slight heel lift under the insole of my shoes to shift my weight to the ball of my foot. That 1/4 inch made a huge difference to my mid-foot pain. So it all depends on what your problems are.
Do you know whether you foot pain is from inflammation (in which case, you really need to push for treatment that will prevent damage), or damage? Knowing this, and talking to the podiatrist could save you a lot of money. You can spend a lot of money getting this wrong, and believe me, I have.
Like tntlamb, I wear variations of the hiking boot: my runners (as if I could run!), my slippers, and my dress “shoes” are all variations of a high-cut/ankle boot so that my foot is held tightly in the shoe to keep it from shifting when i walk. I lace my ankles tightly, and the midfoot loosely. (Midfoot is where my damage is.) In the summer, I’ve found that I can get away with Crocs flip flops as long as I don’t have to walk too far. That foot bed just happens to work OK for me. I’ve tried other brands that look similar, and they are instruments of torture. Looks mean nothing.
Good luck, hope this helps. I’m so sorry that this is a problem for you.