Boots
Daphne: Hope you don't feel like screaming "Too much information!" yet, because I can't resist putting my two cents in.
I wear an Ariat brand paddock boot (short boots, they lace up) and I can't say enough about them. They do not have a smooth sole, there is some texture on the bottom. I have no fear they'll slip through the stirrup, they feel quite solid and nice. They were costly: $160, but I love them to death.
They are comfortable on and off the saddle, and I would wear them with jeans and even some sportier long skirts.
I have worn mine without and with half chaps, and find they are just the best things going. I mention the brand name because I felt they are THE most comfortable shoe I have EVER put on. Especially good if you have high arches, since they give you lots and lots of support.
Best thing to do: go and try on EVERYTHING in the tack shop. (Don't look at the price, just try on). If you put on some shoes that make you go "ahhhh", then seriously consider them. $$$ are always an issue, but I have to say I have learned to go for it when the fit an the quality is right.