Oooh, that's a toughie! I would say get the Jumbo now because the prices keep going up, but then again, you can always get the Jumbo later (if you don't mind paying more) because the design will be there, but the boy bags are seasonal (as far as I know they've never made the same exact ones again, someone correct me if I'm wrong on that). But I will say to get the Jumbo because it's a classic and you will most likely find another boy to love in the future and you can't go wrong with a classic Good luck and please let us know what you decide!