I really like quirky purses... the canvas bags with funky images on them. I do NOT like the bags with tinkerbelle, tweety bird, or any of that lame shit, though.
I want my purse to be basically simple. I don't like a lot of sections. ONE additional pocket to put my phone in is ideal.
I organize my purse with smaller bags. I have a pencil pouch, a pouch for feminine things, and my wallet/checkbook. This way, I'm not digging for what I need. It doesn't always stay as organized as I prefer, but it works out a little better than just dropping my stuff into a bag.
I need to be able to sling this bag over my shoulder. Handbags will be promptly mislaid.
I also need to be able to put my book and moleskin in this purse, so it needs to be substantially sized (but not stupidly gigantic).
This is the kind of bag I tend to carry (note silly little image, simple design, and sling-able straps):