I love the Montaigne because I don't usually carry a lot of stuff but it holds even the few things I carry without looking empty and silly, and yet also holds a lot more when I do need to carry more for some reason. I love that it is just structured enough to wear with business suits, yet also slouchy enough that I don't feel silly carrying it when dressed casually. I like having the zipper for security, but I also like the way it hangs when the zipper is open - it doesn't gape and yet is easy to get into and out of. It is great carried by hand or on the crook of my arm, and if I really need to have both hands free I can also (just) fit it over my shoulder - it isn't ideal but does the trick for a bit when absolutely necessary.