For about the last ten years I've carried a Timbuk2 messenger bag instead of a purse. Sure, I've tried to be a girly, I got a great purse from Harrod's on our trip to London, but I keep coming back to my messenger bag.
My original one was black and it would have lasted forever, but I wanted something at least a little more fun. A few years ago I got a build your own one in shades of green and black. I love it. I keep thinking another bag would be more fun, but I know I would just end up back with this one.
M, being a typical kid, tries to copy me, with sometimes disastrous results. She gets trapped in straps that are too short, or she tries to take my adult bags and gets tangled in them. I have searched to find a kid messenger bag appropriate for a two year old, but no luck. They're either made for school age kids, or absolutely dorky looking. So, I sewed my own. It took one evening, a bit of hand sewing, and I think she likes it.
PS. If I were going to be endorsing products, Timbuk2 would be high on my list. The are indestructible. The ten year old one, still would be fine, I just got bored with black. When work gave us laptops for remote access, I went out and built my own bag for that. When M was born, I didn't get a diaper bag, I got a Timbuk2 tote bag, knowing that I could continue to use well afterward. I have cleaned out ungodly things from the insides of my bags, but still they continue to be awesome. If I had one complaint, it would be that their indestructibility means I cannot justify getting a new bag.