Girls night out dilemma

I am going on a "girls night out" with a great friend of mine and its been a few days of serious dilemma. I haven't been out on the town for years and years and to be quite honest I haven't been sure of exactly how to go about this. You see, I am a mommy, and for the last 7 yrs have been in mommy mode. Yes, I have dressed up to go out to dinner with friends and with hubby, but "girls night out" has long been faded out of my memory.

Firstly were do we go? I am driving alone so having a few drinks and saying " home James", is not an option. Plus they always have road blocks near my neighbourhood. Then, what to wear? Now, if your a woman you know exactly what I am talking about. You gotta have the right outfit, and since I am a jeans and t-shirt person that just doesn't cut it! So, off to the shops I traipse and spend hours and hours looking at awful clothes. I find some great shoes and a stunning skirt and now I worry, oh hell, I don't want to look like mutton dressed as lamb.
Then my friend and I settle on a location, in fact a few in Kalk Bay. Brass bell for dinner, Cape to Cuba for a possible cocktail and then we might try Polanas. Polanas is a great day time spot and its so beautiful as its located right on the waters edge with the sea almost coming into the restaurant. ( In fact it has before!). As a night time spot its can be full of drunken guys looking to score, and good if your young and want to be picked up, or divorced and want to be picked up. Plus its smokers paradise. So, being a happily married non smoking woman its proberly not the best place for me to be. The last thing I want to be is hit on. My ego doesn't need a boost and my self esteem is okay!
But I am still super keen to get dressed up and have a great time whilst leaving my husband to baby sit.

Little black skirt, and super shoes...here we come!

Similar bootie shoes to the ones I bought.