I'd choose my large soho tote. Its big enough that I could sneak some smaller ones in there.
Since I am only allowed one bag at a time I think this decision is pretty easy for me. XD
Probably something big, black and all leather.I have a 3 year old and I'm always carrying around something of his! I'm still learning all the collections, but this one looks awesome! It's the Hampton Pebbled leather business tote.