Dress warmly and take good care of your health (Unlike these damn young kids I see each morning waiting for the school bus wearing wind breakers when it's in the teens.  Tsk tsk on their parents.)

There'll be plenty of time to help you out of those things once were ensconced in a nice warm bed.

Remember...

it's what's inside that counts!!!

While in a hotel lobby so I want to look like a DC tourist much more into being discreet with my affairs... I am nice looking enough that someone is going to notice me or strike up a conversation while in passing anyways. Pants and comfortable walking shoes/ boots with a generic overcoat is my lobby wear. My heels are usually in my purse and switch to them on the elevator up. Once BCD, he can undress me in my nice pants and a classy sweater... Of course what's underneath is what is the most important, always a nice lingerie set! I don't have the uber picky clients that need that require high fashion when it's below freezing outside. Dinner or a specific request, well that's different, but I would expect my date to match so it's not that obvious that he's with a hooker. Lol!!!

...tacky. They should work with whatever else you're wearing of course.  

Tight jeans, heels (boots or regular heels), frilly blouse, and a fur coat look hot to me. Same for casual slacks or a suit. Yep, I like it.

there's no need to worry about it.  The clothes are coming off, anyway.

just rock whatever you wear. Jeans and a winter coat can be yummy!!!!

...I like to hit the slopes every chance I get.

A big coat & boots if it's sloppy out.  Only a fool would risk ruining fashon shoes in the snow.  Dress pants on nice jeans??  Just fine.  Coat should cover nearly to the knees.  Re-do BCDs.

arriving at the outcall location, change in the restroom to more sexy attire.

Two of my favorite dates of all time showed up in a parka and Uggs....it doesn't have to be about the FIRST outfit of the date...

Pants are fine! And jeans can be damn sexy!!!

I live in the cold.  I would much rather that a lady arrive safe and warm than cold.  Frankly, it's not she's wearing at the beginning, but rather, how little she is wearing a bit later.