I always bring MORE shoes rather than fewer. It's counter intuitive since they take up space, but I walk upwards of 12 - 15 miles a day when I'm in the city and I love to look at least somewhat fashionable when I do it. So I switch out my footwear a lot. A change is as good as a rest. Of course I only bring shoes that I know offer comfort in regular conditions in the first place.
Take a look at Angie's "capsule" wardrobe posts for inspiration. I would bring: a trench coat, a great blazer and maybe one other topper (cardigan, leather moto, etc.); 8 tops, 4 bottoms, plus a dress that can be easily mix and matched, with accessories to go with. Start from the ground up -- what looks best with your chosen footwear? And go from there.
