Shopping, right clothes and acting young

As each of us know we all wish to stay younger and try to achieve this everyday we live, many of us girls that were men at one time still think we are still that young lady and try (and I mean try) to be that young lady in the way we dress.
I chose an older style dress because I know I wouldn't look like that 20 something in a short skirt showing the world a fantastic body instead I felt comfortable showing the world who I am - I am Ms Shauna B and I am proud of myself for who I am.
It has taken me from my male self and transformed into a lady I have always known I was, I pushed myself out into this world we live in because I wanted to be happy again.

I do so much for people that I forget about my needs and this is what I needed, now I hope the world doesn't turn it's back on me. With that said, I am going out in public with a very special lady and her friends in March, I will pick out my proper clothing, not the skimpy clothing all my younger girlfriends wear ( though I wish I could) but not an old style either. I am thinking a skirt or pencil skirt and blouse, with a 3 inch heel and hopefully I don't fall over and break an ankle lol. If I was bisexual I may say that I would attract a mate but since I am staying straight (lesbian) I too hope she loves me for who I am about to become.
Everyday is a challenge with buying the right clothing, analyizing the path I am on with my transistion and just being who I am. I am on the right path because in my heart and mind Ms Shauna lives because she has strength and many friends who advises me on what to do and what not to do, I started here as a victoria secret (LOL) and here I am my own angel. Now the silly question ladies, how do I get the right measurements, do I go out in man mode or as Shauna to get these? I wish I had more girl friends to do this. So much to get, I have a $2000.00 off to the side just for my clothing line, shoes, lingerie, accessories and clothes will a $2000.00 be enough?See there is so much to learn here, I am starting over and this isn't a game either, I want to look right and all advice is taken.
Well enough for now, let's see how I do on my own?
Hugs, Shauna