Inspired: Mad Men Hair & Makeup

Now that I've shared with you the inspiration for our engagement shoot, it's time to actually do some planning for hair & makeup.  

I wear makeup EVERY SINGLE DAY. Not a ton, but I feel completely naked and not very pretty without it.  I've worn makeup daily since 8th grade, and feel that I am pretty good at doing my own makeup.  (That being said, I will be getting it done professionally for the wedding because I love getting my makeup done!)  But for engagement pictures, I can handle it on my own.  Being that we'll be in Atlantic City, I think it would be a hassle to try to get someone to do my makeup for the day.  Also, I'll be doing my hair myself.  I am not great at doing much with my hair, so this may be a bit of a struggle.

For our Mad Men themed photo shoot, I'd like to look something like this...

Christina Hendricks / Image via Soap Net

I don't ever post pictures of me without make-up on, but for the sake of posterity and seeing what I'm starting with - for you guys, I will.

Here I am, without makeup on:  (I'm cringing as I even type this!)

Ok, whew.  (I saved you all the horror of having extra large photos of me w/o makeup)

So, for this look, I think the eyes have it all.  I have this kit by Bare Minerals, that I thought would help me create this look perfectly.

bareMinerals Face Fashion - Classic Glam

Here is how it turned out:

 Close ups are weird and I never take pictures dead-on -- you can see why! 

Overall, I'm please with how the makeup turned out, even with the weird closeups. But unfortunately, makeup doesn't complete the look. Next up, the hair...

Here's how it started:

Lots of hair

And here's what I came up with:

It's nothing fancy, really just swept to the side in the front, and I rolled pieces of my hair and pinned it in the back. It took 10 minutes, maybe. I have no pictures of my from the back, but it's really just a mess.  I need to figure out to make it neater.

So what do you think of my Mad Men inspired hair/makeup?  Any tips for improving the look/help me create a neater up-do?

Edit: I went to the grocery store like this... and got some interesting looks! Maybe it's just too dressy for a trip to the store, but maybe it looks terrible? Thoughts??? Am I just paranoid?