I've had issues with plantar faciitus for years and have inserts for most of my shoes. I find that I don't have to wear the inserts all the time or in my boots. Look for boots that are comfy and have good arch support and a snug heel cup. Since I'm only out in the woods typically for only 5-6 hours at time, I've been comfortable in my Carolina waterproof steel toed logger boots even though the heel seems a little too high. Our woods has mostly uneven sufaces and there isn't much flat ground here. I much prefer a boot with the lug soles and a heel that can dig in. I've slipped many times with other boots with the smoother soles. The smoother soles were much easier to clean off and sneak in the basement door and get a beer or soda out of the fridge down there. The lug soles drag in more dirt and I get the evil eye from the wife, but she does understand the safety aspect of good traction on the side of a hill with a chainsaw rippin' at WOT. Dirty boots in the house is a hangin' offense according to Judge Jenny... LOL