Living in Chicago, we are forced to be out in the elements. I made this realization the first year I moved here, misjudging how impossible it was to run a few short blocks from the El to my office. I spent the entire workday waiting for my clothes to dry, and angering a few of my co-workers trying to dry off with a spaceheater that ended up short-circuiting their computers.Since that time I have figured out how to stay dry, while still looking nice.
Tretorn Plask Boots: Not only do these keep you dry, but they are really cute AND comfortable. They look so nice that you don't even have to change out of them. I end up getting a lot of compliments whenever I wear them.
Crocs Prima Ballet Flat: I had originally bought these for a trip to Spain where I needed a comfortable walking shoe that still looked nice. It wasn't until it started raining on their Santa Semana parade that I realized how lucky I was these were waterproof too. Plus they're really lightweight so I can throw them in a purse of bag if I suspect I will get caught in a storm.
Trench Coat: I bought a trench coat from Kenneth Cole a couple of years ago and I still wear it all the time. It's perfect in rain because it will keep me warm and it's long enough to cover my skirts and dresses.