a fashion question: what in the heck should i wear for date night

First and foremost, a disclaimer: I am not posting a bunch of pictures of myself, from the chin down, in various outfits because I think I'm cool.
It's quite the opposite actually: I am not in tune with fashion whatsoever. But when a date night comes along (as they do about every four months) I try to step it up a bit. And I need help.

Other disclaimers: bad lighting, bad background, bad photography (sorry, hun, I know you did the best you could with our little cannon point and shoot!)

Moving on... the date is to the OBT's Nutcracker dress rehearsal which my husband obtained (free) tickets for through work and secured grandparents to come babysit all without my knowledge, which, obviously, is getting him some major amazing husband points.

Onto the outfits:

#1. I thought this would be my favorite, and it so was not. It is comfortable and I love the necklace, but I definitely felt a little Fräulein Maria, if you know what I mean.

shirt: thrift store

necklace: thrift store

pencil skirt: Costco (woot, woot!)

flats: Born (my mom decided they weren't her style and gave them to me)

clutch: Alfani (?) Macy's sale forever ago

#2. A couple issues with this one: first, the blouse is just long enough to be tucked in, so I couldn't put my arms up at all without it becoming un-tucked. Which probably wouldn't be a problem because you don't have to reach up for anything if wearing heels makes you an amazon woman. 

Other problem is that I may break my neck if I attempt to wear the heels.

shirt: thrift store

jeans: Citizens via my mom 

(do we know each other well enough for me to admit to you that I am a jean snob? Jeans are the only thing in which I have expensive taste.)

heels: Nine West

#3. By far the most comfortable (can you tell this is a priority for me?). My mother-in-law gave me the top when I was eight months pregnant with James and I wore it all I could for the rest of my pregnancy. To say something is flattering on woman who is about to deliver a 9lb 5oz baby is saying a lot. 

Also, can we just talk about the flats for a minute? I love these shoes, but they have poinsettias on them. (Yes, as in the bright red Christmas flower.) Which makes them wearable about one month out of the year, the very month where it is way too cold to go out without wool socks on. Thus, it is very exciting for me that this outfit incorporates them.

sleeveless top: gifted (Thanks, Shir!)

three-quarter length cardigan (under the top): Target

flats: from some little shop on 23rd, purchased forever ago

So, I am serious about this, gals! I will wear whatever you vote for. Feel free to mix and match also, as I may not have put the pieces together in the way they should go. 

With much appreciation for your style help,

Ashley