Fall Footwear

As much as I love the summer, my thoughts start turning to fall by the middle of August. What will I wear? Is there anything I should be saving up for? The other day I was thinking about what to do when I have to wear something other than sandals, and I don't feel like I have "real shoes". I have little garbage runners that I wear to work then try to remember to change out of before any customers see me, but they certainly aren't stylish or professional. I love the look of all these Oxfords, but I don't want anything that makes my feet look big, or have too masculine a vibe. Would these look good with jeans, pants, leggings? There are the lighters, almost jazz-shoes looking ones, but I definitely need something sturdy and waterproof-able. I might have to make a nuisance of myself and go to the mall after work every day for a week and try them on with a bunch of different outfits. And then, black or brown?