I have had five diaper bags, i currently have three still in my posession. I started off with a very cool looking Kenneth Cole backpack that my neighbor's sister got for me a cost or something (she used to work there). It was just too heavy on its own (it was vinyl) and the straps were too narrow and everything got lost in it.
Next I had a combi urban sling messanger bag, which I thought I would love because it was so light and small. It was too small, though, for traveling with a toddler who needed a cup and snacks and toys and cloth diapers.
I have the weebees bag for travel, and I really like it for that. It's great to use as a carry on with the baby because it holds so much. It's way to enormous for every day use, though.
I thought I loved the mom about town bag, until I realized that there was no way for me to stop DS from stealing my wallet and taking everything out of it. That bag needs a zipper, somewhere. Also, it doesn't close up tightly at all, so it's not so good for tossing under the stroller or anything. I still have it, though, because it felt like a splurge.
Right now I'm using a Mackenzie kids small bag that can be carried messanger style, or as a backpack. I like that it's compact, but it's a bit too small. It's making me almost wish I had kept the combi bag in the first place. I did get it at Right Start when they were clearancing, so I didn't pay too much for it.
I keep wanting to order a custom Timbuk2
messanger bag, but when I add everything that I want, it gets pricey, really fast.
Plus, DH makes fun of my bag obsession. Oh well.
Man, did I go on and on or what?