I think it would look really cute on you. I'm thinking for every-day, runnin' the kids to school, dodging the clingy mommies, hanging at soccer games, you might be able to do some scrunching since it seems you have a little natural wave...leave the curling iron for girl's night out and nights w/Mr. F. Plus, having had my hair several lengths of "short", I can say that you'd still probably have some ponytail option with that length (since it's a little longer than it appears due to the cute curls).
I just went through what your going through. I made the wrong choice. I hope you don't. I'm talking Jamie Lee Curtis short. OMG. To beat all, I'm not pretty, feeling like a dip right now.
I have always felt like I was hiding my insecurities behind my hair. Like no one is really looking at me but hair mostly. Then I got brave, gheesh, I wish I hadn't.
I'm miserable feeling so ugly. My pageboy type style or swingbob was so much better for me.
YOU WOULD HAVE TO CURL YOUR HAIR EVERY DAY.
I have long hair and a new baby at home. I was going to recommend that you go with Samantha Who. However, my dear husband, sitting to my left, wants you to just get the usual.
Best of luck to you!
The Samantha Who cut is adorable and would look fantastic on you...but I voted for the usual because I'm the woman who cuts her hair short and then HATES IT because I can't just put it in a ponytail and go...and I don't want you to be that woman too. Maybe start with somewhere in between and see how you like it? Then you could cut a little more, and a little more, and the trauma won't be as great because you can adjust a bit at a time.