Date Night-ing

I'm not a girly-girl (Quatre take note) and I don't really know how to do dresses (I've made some improvement this summer) so if I was to go on a date, my outfit of choice would NOT be a dress or skirt especially if its a 1st date or something.
I will gravitate toward dress pants or I'll do a dark jean paired with a nice top.
Footwear-wise, I'm still on the fence...I'm not sure if I'll do flats or a small heel like this: by the way, I love these shoes...I call them my power shoes because of the sound they make when I walk...*clack...clack...clack...clack*...Plus, they have an awesome color...deep blue...in case you couldn't tell from the pic!!
I don't think I would do a higher heel because I want to be comfortable for the date...no fidgeting with shoes or whatever!!!

So my whole look might look something like this;
with a sweater or jacket over it...OR this: I wouldn't change anything about this outfit...I would wear it as is...

If in the off chance that I wanted to wear a dress...I would like to wear something like this: its fun, flirty and appropriate (I think) but I don't think I could pull it off...I'm not sure...its one of those things that I like it when I see it but I'm not sure if it'll look nice on me or if I'll feel comfortable in it...I would like to try it on tho...***plus I'd have to figure out shoes to go with it...ugh...what a chore...just joking...or am I?!***
Generally, I think a form-fitting dress would be perfect for me and I would have to make sure its comfortable.