Classic WOC or Boy?

I don't think you could go wrong with either, it just depends of what style you personally like better. I have a mix of WOCs, including boy and classic styles, and I probably like those 2 styles almost equally- If I really had to pick one, though, I would probably go with the classic style just because I like that the logo is more discreet and I think it can be used for dressier occasions better.
 
I prefer the classic quilted version because it looks more clean for a small bag (just quilts, no border, simple cc Logo). Although the snap button is not the easiest to close with one hand.
 
I went back and forth on these two for a while and just bought the classic version yesteday. I like the look better - cleaner and a bit descrete. Same reason I didn't want to wait for the mini