For me , this choice is easy! The RILEY, hands down! It is such a gorgeous bag and it is certainly more functional. It has a huge outer slip pocket on the back which is so great for your cell, or things you need quick access to. It also has the zip top closure which I prefer to totes, because it prevents your belongings from falling out of the bag, should the bag fly off your car seat, or something like that. The Hamilton has no outer pockets at all! Not only that. I flat out think the Riley is better looking. I see too many women wearing the Hamilton and who wants to look like everyone else? Not me! Be different! Get the Riley! Why mess around? Get the large! lol! The Riley is stunning!