Clothes...

Over-thinking this hobby is suspicious

...you want to look like you belong.  As George Gobel(who?)famously said: "Did you ever get the feeling the whole world was a tuxedo and you were a pair of brown shoes?"

Another factor is to behave as if you've been there before. Walk confidently, nod or say hello to those you may encounter.  

The ladies just want you to be clean and wear clean clothes.

From what I've heard, it's more about being respectful,

clean, on time, and putting the right amount in the envelope.

Once in a while I see a post saying don't knock on the hotel room door so loudly.

I have yet to see an FAQ page or post that has what to wear on it, the ladies don't seem interested in that.

TC

I always dress / carry things for the location.  Not a big deal but try to fit in.  
Put the d*mn cell phone away.  
Don't look like you're going on a civie date!
skb

Seriously, nothing beats what God provided.

Clothes dont matter, just shower and shave your pubes.

Anything that has a pocket in it for your wallet will do fine.  

jeans, sport shirt, tennis shoes.

What about if you are going with the lady to a dinner date? Do you coordinate to avoid looking "mismatched"?