One thing I see a lot that always bugs me is listening to an ipod while riding. Nevermind the headphone cord, I need to be able to hear what's going on around me. I do however keep my cell in my front pocket when I ride, just in case something happens.
Shoes with a heel (still rocking my 10 year old blundstones and half chaps) and long pants have always been standard to me...always a sports bra and whatever shirt as long as it's relatively close fitting. If it's cold I'll dress in easy-to-remove layers, no pullovers or anything like that.