To set the stage here, you have already seen each other a few times and get along wonderfully. Which obviously the beautiful lady is the one of your choice so she is built exactly how you prefer. You are meeting at her place and she offers to dress any way you prefer, within reason of course. She tells you to give her five choices and then she will decide how she will be dressed upon your arrival. In order of preference please rank the following five or feel free to keep a few or throw the list out and create your own.  

or spend money unless the man of the house gives his permission. They cannot commerce either.

6. Nothing

2. Simple (but short and tight) dress with lingerie underneath.

for the lady to be wearing a dress shirt of mine that I have given her from a previous date. Either a very lacy bra or none at all. No skirt, shorts, or pants of any kind just a nice pair of panties.  

6...babydoll dress with stockings and heels, bare

When you guys answer this, are you thinking about how the girl looks in these outfits at all? I wonder sometimes if men think about that when requesting outfits. You may like how she's built, but that doesn't mean everything will look right on her, even in your eyes which are biased of course. For example, you may find jeans and the cami super sexy as an idea, but if you put that on me - per se - it usually looks ridiculous. I have long legs for my height, larger than average breasts and barely a mid-torso in between them and only top off at 5'3 or 4. I never wear jeans when I want to impress someone unless they specifically ask, and then I'm usually like, "jeans? I don't own any jeans, lol". I once had someone request short-shorts like daisy-dukes and a tiny top. Once again, I was like...."uh I would never be caught dead owning short-shorts." We're not all former sorority cheerleaders, lol.  

in truth, I like to have a gal wear what makes her feel sexy.  I think that would make us both the most happy.

I always give the option to the lady to wear whatever she feels sexy in but often she says what would you like me to wear? There are obviously more options than the five listed. I just thought this was a great lead in. It is all about the ladies feeling respected, wanted and special. If she asked me to wear something that was within reason I would wear it. Why? Because she asked....

Would be my preference.  I am struck by how often I am asked to wear something simple, like a white shirt and straight skirt, or a nice dress, like I might wear to an office, you know, when it's just inside my incall.  It's sweet.  What is it about a simple button down white shirt -- maybe a work or school teacher fantasy?  Isn't it funny what sexy turns out to be for different people and how surprising it can be, what turns them on?  Anyway, hard to say why it works but very easy to do!  Oh and stockings! Stockings drive everyone crazy :

5 is definitely "meh." don't care for lingerie.
I would add:

a simple, short and flowy summer dress is my personal preference and what most of my friends seem to prefer as well. i am definitely much more "cute" than sophisticated and seductive.

many men, particularly those not experienced with purchasing clothing for women, have absolutely no idea how clothing will translate onto an actual female form. they think...the clothes are sexy, the woman is sexy, hence together they should be uber-sexy. and of course we know that is not the case.

I don't do wardrobe requests that are out of my scope or comfort level. If the particular request means that much to the guy requesting it, I suggest he find someone else. I know what looks great on me and what I feel utterly silly in. And it will translate into how I am in the session. Not fun for him or me.

I have always been a fan of a sundress on a beautiful woman, with the right lighting showing her figure through her dress can be amazing.

For many years I would think that an outfit made a woman stunning!