I also think that you should try them on at the store. I am 5'1 and I like the large size better. I am used to big bags though.
I am 5'4 and love my large Hamilton.
I'm 5'9 and I think that the Hamilton tote is the perfect size for me.
Check out the modeling thread or Hamilton threads for reference picsI'm sure you'll find many pics of people modeling Hamiltons (and most will state how tall they are so you can get an idea of the bag will look on you). I'm 5'4 and personally don't find the large Hamilton too large.
I'm 5'2" and have both sizes in the Hamilton. I find the large size to be way too big on me and only really use my smaller Hamiltons. You have a couple of inches on me, so the large might work better for you! Best bet would be to go to the store and try both sizes on so you can determine which one is better.