Mission Impossible: How to be a lady at work for 8 hours straight

First of all, wow. It's been awhile since any of us have posted. Man... a lot has happened. We spent some time together in a sunny locale; have each gone through personal triumphs and challenges. But that's all I'm going to say about that right now. I have a couple of questions to pose to the universe that pertain to my lady status. Specifically, my office lady status. I need help.

My problem, simply put, is that I don't know how to maintain my ladylike appearance for a whole 8-hour workday. It's not so much my demeanor that I'm concerned about - I start off a bit gravely and soften as the caffeine levels in my body bring me nearly to the point of convulsion, and then I level off for the rest of the day. It's mostly my appearance that I'm worried about. For whatever reason, regardless of how ironclad I feel wardrobe-wise in the morning, the facade starts to wear thin shortly after lunch and then I'm basically professionally threadbare by the time I drag myself out of here at 5 o'clock.

As per usual, I will accompany my sentiments with related photos that I have dutifully searched for on Google. This is how I feel when I come in every day - note: this is how I feel... not necessarily how I look. Because I would never wear a suit jacket. Ever.

Cool. Confident. In control.

I consider it a small miracle that I am able to achieve this because I am not at all a morning person and usually am putting my "look" together while I am in a state somewhat reminiscent of this:

Coffee. COFFEE NOW!

If all of my barely functional synapses are firing at a reasonable rate, I am usually able to pull together an outfit that is acceptable. My make-up routine is rather rote so that doesn't take very long, hair is usually not complicated and then I'm out the door with a full travel mug of go-go juice, ready for another 45 minute morning commute.

After said commute, I typically arrive to work feeling pretty good. Kind of like this lady:

Sure my jacket is slightly wrinkled from the seat belt, but otherwise I'm good right?

Things tend to stay this way for a couple of hours and several cups of coffee, then it mysteriously, but without fail, starts to fall apart.

My job is fairly predictable, so I'm not usually running around like a crazy person doing things that require athletic wear during office hours. But at the end of the day, I feel - and more to the point, look as though I've been put through the ringer. 

"My god - what happened to you at work today? Were you fighting off crafty marauders again? Saving the world? Swimming with piranhas?"

"Nope. Just made a couple copies and sent some emails." 

So my questions at this point are:

1. Am I supposed to adjust my wardrobe in any way when I arrive to work? To account for the natural phenomena that will occur while sitting at a desk for 8 hours like wrinkling and coffee stains?

2. If aforementioned adjustments are necessary, what are they?

Now in addition to my clothing transforming magically into a hobbit costume once its been on my body for a few hours, there is also the issue of makeup. This, I suppose, may speak to a more Emily Post sort of issue, but regardless it raises an important question that needs to be answered:

Am I supposed to re-apply any or all makeup in the middle of a work day?

This is important because my face melts while I am at work. Apparently. Not my flesh, but basically everything that I put on top of it, which is not very much at all. Refer back to the first photo; generally clean, relatively light makeup, but enough. Then, around 3 p.m., I turn into this:

My makeup has fallen and it can't get up.

Sometimes, I will re-apply lipstick but not usually. Whenever I do this I think of that whole "lipstick on a pig" thing that our nation's most reviled hockey mom said a couple of years ago and I refrain, choosing Chapstick instead. And I never, ever, reapply any other makeup... ever. Sometimes I'll use those Clean & Clear Oil Absorbing strips to address any shiny areas, but nothing more. Am I supposed to be doing more? And if so, what?!?!

The reason why I care about this at all is that I've started to get called into late afternoon meetings and some after-work engagements where it would be nice if I looked like a decent human being rather than something that got scooped up by a street sweeper. I've purchased fashion magazines, watched online segments about fashion by people who have good fashion, and I still can't seem to get it right. I feel like I'm constantly being bombarded with a slightly different version of this outfit, which I find to be completely crazy:

Who's the woolly mammoth sitting behind that desk? 

I mean, OMG - I'm so sorry. I love your jacket.

Bottom line, I don't do this well. Office fashion is hard. As always, suggestions welcome and encouraged.