A little backstory: I have wanted to present in a more femme, androgynous way for a long time. Since reading the great responses here almost 2 years ago, I basically started and stopped with flamboyant socks (Happy Socks are great). I did pierce both of my ears -- but lost my nerve and let the holes close up. Though I stayed competent at managing my dysphoria at my clothes and appearance (which I shouldn't overstate, but I recognize is real), it hit me recently that this is never going to go away! This is how I am! So I might as well express myself and be me. It actually took a supportive friend/partner who unblinkingly saw me as genderqueer or gender fluid or whatever (nobody in my life has ever thought to ask me what gender pronouns I prefer) to realize that unless I stick my neck out there and act, everyone's going to coast on their socially-set default assumptions, and that part of me will never breathe the fresh air of open expression.
So I've started to act. I bought a few items that called out to me -- a skirt, a couple of dresses, a blouse. I started to shave my legs and armpits. All of these little things feel great. I love expressing my body in this way, which I think of as femme, and just lounging around the apartment in a dress feels so relaxed and wonderful. Last weekend, I just fucking went for it and wore a skirt out shopping and drinking. It was nervewracking, but also kind of calm and chill. My main impression afterwards was: good start, but I can pick a better outfit. In other words, I'm committed to the journey now (as much as admitting that makes me want to yell "never mind!" and forget the whole thing..)
I've decided that to really make this work, I can't just rely on okay skirts and a couple of dresses I'm nervous to wear out. I need to get together an ensemble of things I can mix and match on the fly. I'm thinking that I probably need tights(/stockings/ leggings?) more tops, women's pants, some nice shoes. As per an answer from 2012, I've been looking at queer fashion and really like a lot of the queer femme and various trans* looks. For a wonderful point of reference, pretty much everything here: http://qwear.tumblr.com/ I also think Laura Jane Grace is beautiful and like that kind of punky-simple black and white dress style, as seen here: http://thekey.xpn.org/aatk/files/2013/08/laura-jane-grace.jpg
the look in this video is rad too: https://www.youtube.com/watch?v=0Tcm7yX0-q4
ACTUAL QUESTION: What specific items should I prioritize for a solid starter ensemble? My goal is to actually maximize my everyday usage -- so I'm thinking things like simple spaghetti strap tops, things I can layer, etc. It'll be summer momentarily, so simple things I can wear out proudly are rad too (I like simple. Smart and femme but not like cupcakes-level-cute. Pastels and white and black and purple, I love). I need shoes but don't want to break the bank with them. My budget for getting started is $250 total
Here's a glimpse at my first (very early) attempt: http://imgur.com/bABGc4z
Thank you so much in advance! MeFi has given me so much support and encouragement to grow over the years. I'm really indebted to you all.