I wanted to start off this post by saying that I have been questioning my gender identity for quite some time, but I'm not quite ready to be fully "out" as trans. I know there is a lot of things I will need to do in order to "pass" as my preferred gender (hair removal, legal changes among those), and I cannot yet take these steps. I'm also extremely scared of discrimination so until I pass I would like to stay as under-the-radar as I am able to given the constraints written below. And this is a bit off topic, but even after transition I would like to remain fairly stealth, so I'm scared about things that ask for previous names and the sort; I've heard about writing in something like "available to authorized investigator only" if you are asked such a question, but I don't know the extent to which the confidentiality of that is respected in the US (I know the UK has the "sensitive" process for DBS government background checks, and I don't know if I might be able to at least try to emulate that process post-transition on US background checks by contacting the investigating agency directly).
I am going to be entering the job market pretty soon. I am a college graduate with a bachelor's degree (B.Sc. Psychology) and I will also have a web development certificate as well. I know if I go into the IT field that professional attire is usually not on the same level of formality as with other corporate jobs in many cases, but this is not always the case either. So let's assume that I will be going into a position where either a more formal level of business casual, or even business professional attire is the norm.
I have noticed plenty of professional clothing from women's stores that appear fairly masculine or gender-neutral. Out of respect for my true gender identity I would like to buy as many clothes from women's stores and women's departments as I can, this will also be handy post-transition as well. Some of the items that I thought would fit this criteria include pantsuits (especially) and some blouses that closely resemble "men's" dress shirts. I had heard about at least one pre-transition transgender woman who had bought all of her "men's" clothing from the women's section of a department store (with the obvious exception of neckties, in my case I would also include shoes due to large feet). I read about this from some published website but I just don't remember where, if I did I would give you the link. In more casual settings there is definitely a degree of androgyny I could embrace, but business professional attire is quite heavily binary-gendered so I figure the above approach may help me to "androgynize" or "feminize" the usual "masculine" attire.
I'm also wondering about the extent to which I could get away with some feminine accessories and grooming in a professional setting, including clear nail polish, foundation makeup, eyebrow shaping, wearing pantyhose for socks, among others. I do not like long hair so that is out of the question (should I transition I will probably stick with a pixie cut or something).
I'm aware of other strategies such as underdressing and so forth, but this is really going to be the only thing that would keep me sane in a professional setting. I can deal with avoiding some more feminine grooming and accessories as long as I feel fairly feminine in the clothes I am wearing and the clothes I see in the mirror. I am worried about some of the clothes having a weird fit, which I know will happen in many cases, but this is about the only thing I feel I can do until I feel ready to transition.
If anyone has any suggestions, including suggested brands of clothing, please let me know.