Going Short?

My hair has been an ongoing dilemma since I can remember having a say on how to cut my hair.  Long, short, long, short, this has been the cycle my poor hair has been in since the age of 18 (maybe younger) or so.  I have long hair and get sick of it cause it just hangs there, then I cut it short then get sick of it cause of how often I have to get it cut and start the growing out process again and on and on.  I have spent the last 18 months growing out my hair for my wedding (this past August) and kept saying after the wedding I was going to get it styled somehow.  Well, here we are in December and I still have long straight hair with minimal long layers and it looks the same day in and day out.  To make an already long story short I am thinking about cutting my hair again.  I have had a bob before and thought it was cute but do you think I can pull this off?  I don't typically look to celebrities for fashion or follow them at all but I happened to come across these pictures of Paris Hilton and thought that her hair was cute.  Any thoughts?