You can almost always make a wardrobe request to a provider.  However, she may or may not have the type of outfit you ask, but there is no harm in asking, and do it in advance after you have confirmed your date.

Flowers are generally not a good idea for a gift, from what I have read, regardless of where you are meeting her.  Especially, if you are meeting in public before going to the room.  If you are acting like you belong there, carrying some shopping bag is not going to raise any eyebrows, I don't think.  I always bring a gift, candles in a WalMart bag, with a VicSec gift card in there also, never had a second glance.  

People who stay in hotels frequently have to go out to pick up some small things they may have forgotten.  If you are talking about hotel, where there is no place like WM around, well, you will have to figure out something else to carry it in.

Good luck,
Swim

I searched but couldn’t find the info I need. I guess I couldn’t find the perfect keywords for the search.

Now then...

When seeing a provider for the first time, is it appropriate to make a wardrobe request, and if it is, at what point should one make this request? FYI, I’m not talking about anything wacky - no full wet-suit and a tutu - but rather the other way, as in casual.

The other question is what is the best way to “come bearing gifts” on an incall at a high end hotel? I imagine the last thing a provider wants in this kind of place is attention, as a parade of guys coming with flowers or shopping bags, etc. will get noticed, so how should this be done?

Thanks, Swim. I was thinking around the same lines, but I feel far more solid about it now. I appreciate your help!

her to wear what she was wearing in that pic.

Requests should be made after you have been screened.

I do not think there is anything wrong with requesting a lady wear a certain item I would recommend requesting this after screening is done.In the past I have asked guys if they have a specific attire request or he has brought it up first.If you have a small gift I would recommend putting it in a walmart bag or something similar if it is something you cannot fit in your luggage.
Good luck to you!

A request for casual or dress-up should never be an issue.  It's even easier if you're including dinner as part of it.  "I had a nice casual restaurant picked out" is always a harmless way to handle that.

Gifts?  In a briefcase, in a non-descript bag.  It shouldn't be anything large anyway because she'll have to carry it out and you don't know how much she has already.  Earrings, gift cards, etc. fit neatly in your pocket.

Once I've been screened and the date is set I will usually ask, "When is an appropriate time to make a clothing request?"  That way, if she feels it's premature at that point she can tell you before you make a faux pas.  BTW, I have never had a provider say it was premature at that point.