For fall and winter I have a comfortable pair of suede booties that the top folds over and has cool color pattern. I think they've been my all time favorite shoe so far so much that if there was an unexpected drizzle and I didn't bring extra shoes... Yes I did look like the crazy person walking with plastic bags on my feet.
I have a pair of Justin cowboy boots that I've had for about 3 years. they look like hell but they're broke in and the leather is soft on em. That may not be very fashionable but where I come from the girls like worn down boots so it works itself out lol.
Pairs? As in more than one set of footwear? Wow, such luxury afforded to some people. I have one pair of boots on their last legs. I have to make them last long enough so I can get enough money to buy another pair.
My black converse. :) They're comfortable and very light and easy to walk with, regardless if I walk for 5 minutes or several hours. During the summer I mostly wear ballerinas, but otherwise I always wear my converse, even in the winter haha.
I alternate between wearing my blue and orange flip flops and my hightop white chucks. I usually wear my flip flops when I'm too lazy to put on my shoes or I'm rushing. I used to have an awesome pair of brown combat boots I'd literally wear everyday, but they smelt like ass and started polluting up the house, so I had to throw them out =/
Red flats that I bought from Target. They're pretty simple, styled a bit like Toms but they have a cute little silver button on the top and the bottom has a cool print so it leaves a pretty neat footprint. They're a cute, simple, functional shoe.