If you have three things like these, you’ll be good to go in a downpour. Simply put your shoes in the tote, along with laptop or iPad and other things you don’t want to get wet. Swap out the umbrella for a collapsible version, if you prefer, and you’re all set. (Note that the three things I chose here are intentionally neutral, somber, even; you want them to be able to work with lots of different outfits and in many situations, and the more neutral they are, the more that’s likely.)