Hi KC,,
I wear AFO's, and I'm wondering if maybe you need a different shoe? What style AFO did you receive? I have the Toe Off brand carbon ones, and have had good success with wearing mary jane style shoes with them. Specifically Aetrex brand. I used to have some photos posted, don't know if they exist any longer (the pics) I will go snap a photo and post again....
The features I found that make a huge difference in the comfort of AFOs are having the strap across top of foot, and the shoe having a removable insole so that the plate of the AFO can be put into the shoe, and then the insole put back in on top of the AFO plate.
Dr Scholls (sp?) makes a product called mole foam, and it can be cut and stuck on the AFO to pad in places where it is too hard against your foot or ankle....
Even in winter I have found that wearing leggings works better than jeans, because the jeans catch on the velcro straps, and once the straps aren't sticky as much as they should be due to stuff accumulating in the grips, the pant legs make the straps come unfastened more easily when I'm walking. But, jeans work so long as you get a wide enough leg below the knee.
I finally found some sandals which would work, actually wore out one pair this summer, and if you are living in an area warm enough to where you're interested in finding sandals, let me know and I'll give you the information on them.
Check out the Footsmart website for the shoes, I get free shipping offers from time to ti e from them, but it never seems like there is a coupon code, they make it so that you have to link through the email they send. I will find the shoe I have that I like the most, and post the link here. (they are a micro fiber and have some give to them, but support across the instep which is key) I also have this same shoe, same brand, in patent leather, and they're cute. Or, as cute as it gets for afo wearers lol.
Aetrex Women's Molly Mary Jane : Women's Shoes : Footsmart.com
If you have a thicker style AFO, I'm not sure if any of the above advise is going to be much help to you...