[Alpha O]

I have custom-made orthotics. I'm not really sure how large yours are, but I didn't get a choice in size and I'd say that mine are pretty thick to accommodate my high arch. I used to have to wear them almost constantly for about a year when I was experiencing severe foot pain.

What I found is that I was most easily able to accommodate my orthotics in boots, just like you can in cowboy boots. I remember when I went to pick them up, I was wearing moccasin boots, and the orthopedist was surprised that they accommodated my orthotics once I took their insoles out. Luckily for me, the fabric that they were made of had enough give that they were able to accommodate the orthotics. Unfortunately, I didn't really try the orthotics out in summer-y type shoes (preferring to wear walking sneakers and deal with foot pain when I absolutely had to wear something dressy on my feet--I don't always make the best decisions :P), and thankfully it's no longer something I worry about (I'm mostly orthotic free now).

Additionally, I've seen my BF's mother wear Mary Janes and I've been told she wears orthotics as well. I'm not sure where they were from, but they looked like they could've come from Clarks or a similar company. I'm not sure what her orthotics look like, and I wonder if she had special "dress" ones made like a previous poster mentioned.

If you're going to go looking for shoes, I would suggest looking for shoes that are pretty padded and have removable insoles. They should already be made to fit a bigger insole than normal, and you'll hopefully be able to remove them to fit yours in. Also, look for shoes that are made with an upper that allows stretch and try sizing up to see if that allows your orthotics to fit. I think Mary Jane flats with removable insoles might be a good idea, as long as they can fit your insole, since they have more structure than a regular flat.

I understand what it's like to have foot pain, and I really hope you can find something that works for you!