Riding Boots
When I decided to get my :f_spider:, I had to take the motorcycle safety course to get my endorsement. No motorcycle riding since I was 15, and that was in 1957. The instructor told us we would need an over the ankle shoe in addition to long sleeves, gloves and eye protection to take the road portion of the course. I didn't own such a pair of shoes at the time, and needed them the next day. Walmart to the rescue. they carry a number of work boots that cover your ankle, aren't truly ugly, and do not cost an arm and a leg. Mine cost me around $30 in 2010. I wear them most days riding. They are comfortable to walk in, and protect your feet from heat and flying objects. Most of them are waterproof. I wear mine when riding, and when mowing the lawn, using the week wacker and edger. They will likely out last me.
That said, I always wanted a pair of real "Motorcycle Boots", you know the kind, black with harness and metal hardware. I checked many shops before I settled on a pair of River Road Square Toe Harness Boots. Cycle Gear carries them, and they don't often go on sale, expect to pay around $160 for a pair. I wore them this morning and as always, they keep my feet and shins from getting cooked by the exhaust.
It has been my experience that one shouldn't buy shoes or boots without trying them on. Different brands are built on different lasts, and the same size will feel very different when you try them on. Bilt, Cycle Gear store brand is made on a narrow last, my foot isn't real wide, but I cannot put on a Bilt boot two sizes bigger. The River Road fits my foot.
I don't do rain if I can avoid it, and rather than a waterproof boot, they tend to be sweaty, I got a pair of boot covers to go with my raid gear.