Need for HELP!

I really love the Auburn shade It's a little more of a "wow" color than Oak. But if you are really conservative you may not like it. I never got an Annie bag but always thought they were very cool.
 
the main difference is that the oak is more demure, less contrast or 'pop'.
the oak may go with everything forever, where the auburn, with it's slight flash, may go with ALMOST everything, except colors that are close to matching it and candy colors.

they are both beautiful, good luck.