Always use a large, shoulder bag, usually some sort of leather (current one is deerskin), that I buy at one of those artisan craft shows. Those pocketbooks tend to wear like iron and last forever. They are almost always zippered, and have outside pockets for me to throw keys and pens into. I pick my pocketbooks for primarily for their usefulness, rather than to be stylish.
Used to have a great pocketbook in college - it was so large that it was nicknamed "The Cow" because of all the leather it took to make it.
For traveling, I usually use this Le Sportsac one:
http://www.lesportsac.com/store/7519_5205.html
I can never understand how women manage with those tiny purses - my wallet is larger and heavier than most of them. How do you even fit a hairbrush in one of them?
