i prefer the hippie but both bags are fabulous... the hippie's crossbody strap is 6" longer than the hailey's making it more comfy for fluffy chicks like me... i LOVE the cool pleat, the soft leather and the soft, wide shoulder strap... i think it is great as a casual bag when worn crossbody but can be dressier when carried by the shorter strap on the shoulder, in a hand or mid arm... i don't know how much the hailey carries but i had my hippie loaded down this morning with big aluminum water bottle and a bunch of other stuff... not only was there still room in it for more stuff but it was still comfortable to carry because of the way it lays against my side when carried crossbody