Another silly newbie question. As long as I don't draw attention, does it matter what I wear for the 'date'? Basic jeans and a polo type shirt with tennis shoes? Do the women care?

Wear nice clothes:

Slacks, a shirt with a collar and leather shoes will make a nice impression.

Be sure that they are clean and so are you.

this subject has been discussed at least once before, but I will repeat my dress code.

Warmer weather, a 'Magnum, PI' type shirt, shorts, and either flip-flops (crocs) or sneakers.

Cooler weather, jeans, flannel shirt over a print t-shirt, and sneakers.

I rarely, if ever, have a date where I am going out on a date to a high end restaurant which would require me to dress even up to business casual.  I'm not really into that.

So far, I have had no complaints from my dates.  And since on most of my dates, we are not leaving the room and the clothes are coming off shortly, so why get all gussied up just to throw them in a heap on a chair or the floor?????

Swim

probably rank higher than what you wear, but first impressions can make a difference. I agree with mrfisher, business casual goes over better than looking like a slob.  I've worn everything from clean jeans (True Religion or 7 for Mankind) iand driving mocs to a suit and tie. Remember, the clothes don't stay on long! Good luck and write a review.

Clean, nearly new sneakers with ankle socks, nice pair of proper shorts and polo short. Except for the brief winter and short spring/fall weather it's just TOO DAMN HOT AND HUMID here most of the year...

I always wear t-shirs and jeans to appointments, as that is just how I feel most comfortable. As long as you are clean they will not care.

While I carefully launder my pink bunny outfit before each visit, I imagine cleanliness will trump style every time.

Like any business meeting, match the attire for the location and occasion. There is no rule on this, but I would try to not look out of place. Here in the Washington DC area you have all kinds (business folks and tourists) coming and going all day everyday. Some of this depends on where you hobby and the location of the appointment.

Primarily she cares that you look, and are, clean, etc. She cares more about the contents of your pockets that your actual attire.

While I do not mind a gentleman being comfortable I do have to agree that as long as you are clean I have no problem.If you are staying at a 5 star hotel and are planning say for instance dinner then of course jeans and tennis shoes would not be appropriate.But,if you are just staying at a regular hotel and do not have dinner plans or anything like that jeans,polo shirt,and tennis shoes I do not see a problem with this attire.I do have to say that I am impartial to the slacks and button down shirt look something about it is a major turn-on for me.

Yes, one should always walk into an appointment as freshly groomed as your day will allow. But I have always believed that it absolutely makes a difference what you wear to a session. When you walk into a provider's hotel room (or she into yours), especially the first time you will meet one another, the lady is immediately judging you. She is making a determination of what kind of client you will be. The client who is dressed nicely (i.e. think a button down shirt, or nice sweater, slacks, shoes...tie, suit and tux are optional ) will be regarded in a higher vain than the client who is dressed in torn jeans, a tank top, flip flops and a backwards baseball cap. Now, can the "clean cut" man turn out to be a worthless client? Of course. Can the "torn jeans" man turn out to be a true gentleman and terrific client? Absolutely. But why start off with a negative impression in the ladies mind? She will never outwardly admit her feelings, but they are there. We ALL do it everyday in our lives. Until we learn more about the person, its human nature to immediately judge books by their covers.  

Conversely, we as hobbyists make the same snap judgments (again fairly or unfairly) about the providers as soon as we walk in to their place. Is the apartment or hotel room a mess? Are there leftover food containers scattered about? Is the bathroom void of fresh towels? Are there signs of a previous client? Did the provider take the time to look nice (i.e. appropriate attire, freshly groomed, etc.)? Again, the provider whose apartment is a mess could end up being your ATF, and the impeccably clean provider could end up being a waste of money. But again, you have already made a judgment about the lady and those who created a negative first impression will have to work that much harder during the session to turn your impression around.  

So while most people will tell you that it really doesn't matter what you wear (the old adage just show up on time with donation in hand), I disagree. I think it absolutely matters how you present yourself by what you wear, how you speak, and most importantly how you act.  

First. Thanks for ALL the great suggestions. Definitely need to step up from jeans and tennys.

But to set the scenario: We're meeting on the weekend, late afternoon and at her upscale/secure apartment complex. Since we're meeting in front of her complex, due to security doors, I'm thinking button down shirt, slacks and dress shoes? or is that "over-dressed"?

The general rule is dress like it were a regular date. If you are the kind of guy who goes on dates with scruffy jeans and a smelly t-shirt than you may need to bring up your standards. I recommend at least a polo shirt and khakis at a minimum. If the girl says you dont need to dress up for her than you know your answer.
Keep in mind you may perceive her as a short term date with a definite ending, but she sees you as a client, so the way to impress her is to think like a client/professional relationship.

The things I usually hear women complain about are not about dress so much as overall attitude and cleanliness. Wash your smelly ass thoroughly and put on clean clothes. Right off the bat you will be in the top ten percent of all her clients.

Be friendly and sociable but do not ask personal questions like if she has kids or whatever. You dont need to know and on the first meet she probably doesnt want to tell you. As you get to know her she may open up more, but never force detailed conversation. Eventually it will scare her.

BE SOBER! This is key. And dont ever offer her any drugs, regardless of whether you think shes "cool" or not. On the first date I dont even offer alcohol. I also dont keep flowers around until I know her allergies.

If she listed any specific requirements you should follow them. This is especially true if you go to meet her at a fancy hotel. Many times a girl will ask on the phone if I've already her rules on the website. If I am clueless she wont see me until I am familiar with them. Some gals are strict about how you hand over the money or what kind of activities are forbidden. Saw a website recently where a gal made it clear she did not shower with her clients and merely asking for such a service was grounds for immediate cancellation of the date. I guess she's had too many issues with it. Seen plenty of girls who dont want you to mention greek or even joke about it.

Its more about action than appearances. Its not like at a club or bar where you have to do 100 things and all of them correctly in order to impress a women in the hopes she will go home with you. You know why she's there and she knows why she's there so a lot of piddly things dont matter. Think of it like calling an old girlfriend over for a booty call. Even though theres minimal stress and you dont have to put on a big show, still try to be decent about it.

One also has to factor in the meeting place. If its a nice hotel (say 4 or 5 stars), you're better off dressing as business casual. Looking too scruffy could get you stopped by the front desk staff, and you don't want to have that conversation... I prefer the khaki pants, nice polo shirt, and sport coat look. That gives you pocket room for the envelope, car keys, and cell phone, and you look like you belong in the lobby of a nicer hotel. Finally, the previous posters are correct- be squeaky clean, use some breath mints, and know her ground rules. Remember, its not a date- its a business transaction, and its best if you ALWAYS keep that in mind.

I'm a sucker for a guy who wears a nice polo and looks a little on the dressed up side. Purple, blue or green polos(nice bright colors) are so sexy!
likewise it's a turn off(for me) if a guy shows up in a stained band tshirt and ripped jeans and work boots.

But really it doesn't matter as long as you are curteous,clean, and fresh.

"One also has to factor in the meeting place. If its a nice hotel (say 4 or 5 stars), you're better off dressing as business casual. Looking too scruffy could get you stopped by the front desk staff, and you don't want to have that conversation.."

This is nonsense. The front desk staff has no idea who you are, and who's to say a guest at  a 4 or 5 star hotel couldn't be wearing jeans, a Motorhead shirt, and Converse sneakers? I would and have checked in to very nice hotels dressed just like that!

You are correct about not drawing attention and that varies with the hotel or community you are in, whether you are going to a restaurant, show, etc.

It also depends upon the lady.  Look at her site--what is she wearing?   An evening dress, jeans, etc?  A mismatch can draw attention even if the individual parts do not:  a guy in t-shirt and jeans when the woman on his arm is in an evening gown, high heals, and diamond earrings (or the other way around).

comfortably but need to wear better footwear.

Jeans, or a pair of chinos.  A button down shirt, golf shirt, or a sweater in winter will work as well.  As for shoes, I am a penny loafer guy.  The ladies notice this, and they always are cool with that.  Leather jacket (high quality) will draw compliments as well.  

Just dress regular, dude.