I would go jumbo! I do agree with some other users when they say the Boy is now considered an unofficial classic, but I still don't feel that it's as timeless as the classic flap. But that's just my personal preference and opinion, you should get whichever you love more and will get more use out of. One thing though, this season's caviar boys is not the same caviar as the sturdy, shiny caviar that everyone is used to seeing on the classic flaps.. it's a softer, more matte/dull caviar. You can't really go wrong with either though, they're both beautiful bags and great choices for your first Chanel. Good luck with your decision! Please keep us updated =)