I only own E/W satchels, I don't have a N/S tote (yet!) I find the satchel to be plenty roomy for everyday use, buy I'm not carrying an extra pair of shoes for a commute or anything like that. At the moment, I just really prefer the E/W shape; I personally find the tote to be a little too boxy. My only concern about the size of the satchel is the security of my wallet. Since it is a shallow bag with no large zip compartment, I try to attach my wallet to the key keeper hook. Wallets with wristlet loops are great for this. The added depth of the larger tote is one advantage over the satchel, I guess. That's why I think the outlet Hamilton is, in many ways, the perfect bag!