I have never really wanted to buy a bag. But I need to carry one. And lo and behold, as I dip my toes a little further into this dangerous water, I find they can be quite fun!
Your situation is different. I don't think you should buy any bootie that bores you; you have lots of footwear. Just do what Jonesy says and wear some of the ones you have.
However, this goes back to that old "boring basics" conversation we had a while ago. Some fun outfits simply won't work as well without some fairly basic shoes. (Contrariwise, it is easy to funk up more conservative outfits with the right statement shoe). Maybe there is a place for one or two basic shoes in your closet.
I will say that my relatively sleek black booties (the ones that Krish pointed me towards) were workhorses for me last winter. They have a bit of an artsy flair (almost witch-like, I sometimes think, in my less positively disposed moments) but with dresses, they look pretty darn good due to the snug ankle, and they are the most comfortable things I have ever worn. Bar none. http://www.zappos.com/josef-seibel-calla-02