1. The daily - First things first, a go-to pair of comfy shoes for class. They don't necessarily have to be dressy, just something for walking around on campus. I like classic Chuck Taylors, my white pair just bit the dust after a few years and a bad rain storm. So I got a classic hightop in gray recently.
2. Booties - My mom hates the word "booties" but I love the suede pair of Steve Madden's I got from Nordstrom Rack last year. The heel is chunky and short enough for all day wear, but versatile enough to be dress up a pair of jeans or down a nice dress. Before I bought my boots, these were my most worn pair for work.
3. Riding boots - It was so hard finding riding boots for me. I have very muscular legs, and I ended up having to get a pair with elastic on the back. It took me a long time to commit to a pair and I decided to wait and invest in ones that will last me awhile. These are seriously a fall classic and can instantly dress up any outfit. I love wearing these with leggings and a tunic, or with jeans and a sweater layered over a button down.
4. Dressy heels/wedges - In high school my version of dressy shoes was a six inch pair of peep toe platforms. I'm realizing the higher the heel doesn't mean higher class. Grab a short pair of very basic heels or wedges. I rarely wear the pair I got from work, but it's a good shoe to keep in the closet for a special business wear occasion.
5. Water Boot - The next time it rains you won't regret getting a pair of either rain boots or (my favorite) duck shoes. My mom and I were out the other day and she said these were really popular when she was in high school. I'm pretty sure they're about to make a come back. I plan on asking for a pair for christmas so I'll have them for Spring when it starts raining a lot. They're ugly at first glance, but these hybrid shoes have grown on me.