I have owned day bags in the past and currently have a giant hobo. The Day holds quite a bit more, but some (including me) don't like how deep it is and how you have to reach in and dig around for things. It is a very cool style though, especially when it gets softer and slouchier with use. I find the giant hobo to be extremely comfortable to wear and very easy to get into and easily reach everything without taking it off. It's not as good if you need to hold a lot though.