"Hair Loss"

I've made a decision.  When I hit 50lbs down, I'm chopping off my hair.  By then it will (God willing only be) the fall/winter.  I prefer long hair in the summer to pull it back.  I would love to lop it off to see how I feel with a shorter look though I doubt I'd stay that way.  The hardest part is (and I mean no disrespect) making sure I don't end up looking like my mom.

I have a hair appointment Saturday and I plan to chat this through then to get some better ideas about what would
1) realistically look good on me
2) not drive me crazy in my face
3) not be terribly hard to style
4) not end up with me looking like Lynn :)

Below are a few of my current brainstorming ideas.  Seeing as I like to pull my hair behind my ear I need to be realistic about any sort of "bang". I also want something I can grow.  I always tell myself I'm not skinny enough to pull off "sexy short hair" so this would be a major step.  In the meantime, I'm rocking my layers.