<brutal truth>
Hmmmmmm... I've hesitated to comment on this but I'm gonna go for it here. Remember, you asked.
Right now, your neck is a bit too large for that to look cute and your hair isn't nearly long enough. You'll get there but yeah, don't wear that outside the house. I'm not trying to be unsupportive but, honesty is kinda my thing and those don't look great right now. Give it another year, do the HRT thing for a bit, and flat-iron the hell out of those things (after a thorough washing, rinsing, conditioning, post-conditioning, etc.)
I do pigtails from time to time. Especially when I'm going somewhere to be flirty/sexy/etc. It's a fun hairstyle but you've gotta take care with it.
</brutal truth>