I adore my Haileys, they are great everyday bags and have plenty of room for me. On the Kristin, do you mean the hobo with the convertible strap? If so, they seem to me about the same size, but the Kristin strap is not adjustable like the Hailey and I think it's shorter, too. I'm getting the hobo tonight so I'll be able to compare side by side. I like the leather on the Kristin better, but I'm one who likes to "pet" my bags, the shiny Madison leather is not so "pettable."