i like this question because iv been wanting to get a pair of boots for a while now and some feed back from the girls is great. Iv been doing some research and personally I like the chukka style boot rather then the military style. Doc martens are nice but for a brand name like that you have to shell out the dough. If there is a Clarks store near by visit them they have nice shoes for example these link I would say a pair of dark wash jeans with brown boots and you can go wrong...if your looking for more use out of them then check out this website link Hope I could help
Boot wise it varies, I used to wear Cowboy boots all the time. Made me stand out since I live in California, haha. However based on what you wearing I say just going with regular tennies is fine.. Black/White converse or some nice vans.