I volunteer at a sanctuary and we actually do a few days of week of therapeutic riding lessons. I wear a pair of hiking boots, the brand is merrell, for sure footing around the arena and the grounds. They come right up to my ankle but aren't uncomfortable and I feel the provide the support I need. But I have also seen a podiatrist and have inserts to correct my arch and a slight lift on one foot.
I would highly suggest seeing a podiatrist, it's really changed the way I walk, and once I got used to having the inserts in my shoes (the ones you can get a the stores, all suck; the ones prescribed and made specifically for you are so much better) I feel 10 times better in the feet, legs, and back.
Also drink a lot of water, and stretch your feet before and after you are on them for long periods of time and that should help too.
I can't suggest a specific shoe though, that is all personal preference. I stay FAR away from any kind of riding boot though, I know a lot of people wear them all around the bar and such, but I just can't do it.
Thank you, trvlingheart. Those are all great suggestions. I do really think I need to see a podiatrist, I'm just not sure it's something I can fit in our budget right now. Do you mind me asking about the costs/co-pays that you had to deal with? How long does the prescription insert last? Do they last years or do you still have to replace them frequently like even the "best" non-prescription ones? I've previously been to a place called Happy Feet before and they sell their own special inserts for a few hundred dollars, which I didn't know was worth it at the time.
I have purchased some Brooks sneakers (Ariel, the female version of the Beast) and they are made for heavyweight-ers and prevent over and under pronation, which can help prevent ankle rolling, and I'm usually prone to doing that even though I seem to have a "normal" walking pattern/gait. Walking alongside a horse, trying to keep up and stay balanced/hold a child up in a saddle and/or lead is quite different from walking around a grocery store, though!
I decided not to wear those sneakers though because they cost so much (about $120) and I decided they would be best put to use as actual exercise (non-horse/sand) shoes. I also thought that something with a bit of an ankle would better prevent sand from getting flung into my shoe, which is why I originally thought a boot would be best.
I have many pairs of shoes, some for each different "need" - ie. Sitting, standing, walking/exercising, as my feet seem to have different complaints with each of these actions. It would seem to be a lot nicer to just have one set of inserts to put into every pair of shoe.