I have both bags and I LOVE them both. I guess it just depends on what you prefer. I like the carefree feeling with my grayson (don't have to worry about protecting leather). But I like the extra space in my Hamilton, it's got me spoiled. Lol. The Grayson seems more of a casual everyday bag, it's one to could run to the store with in you sweats. Lol. Really I love them both pretty equally, sorry I wasn't much of a help.