I had this same dilemma and after much agonising, I went for the classic. I actually prefer the look of the reissue but I just thought you couldn't beat the classic CCs on the classic bag. It is instantly recognisable as Chanel and my BF thought that for a non-expert, the reissue isn't so obviously recognisable as Chanel. And considering the amount I spent on it, I damn well want people to know it's a Chanel!!! I will be saving up for a reissue though because I think they are both must-have bags but if you are only going to get one chanel bag in your life, I would get the classic.