To Chop or Not to Chop?

I've had long hair since I was about nine.  When I have managed to pluck up the courage and ask for more than the usual trim at the hairdressers (which is very rare), my hair has never ventured shorter than my shoulder blades.  I think that long hair is feminine and pretty, but some girls out there can pull off a pixie or bob cut beautifully.  I admire their boldness and confidence and, as we all know, with confidence comes sexiness.  The ugly truth is that I am too attached to my hair and it is due to vanity, which is why I would love to chop it off and prove to myself that the unhealthy 16-year attachment can be cut along with my locks...plus it will always grow back right??  Here are a few possible replacement styles:

1.  The lob (long bob) like Ashley Olsen:

2. The sweeping bob like Keri Hilson:

3. The messy bob like Victoria Beckham:

I'm also desperate to try a bombshell blonde colour, but that's another story!