I am going to preface everything I say by noting that I do wear makeup, and love the creativity that makeup allows. Ever since I began transitioning, makeup gave me such freedom in allowing me to play around and be creative, and see a sort of mini-transition occur before my eyes. Mahsa, I see where you are coming from, but I have to say I disagree with you completely on this.
I honestly think that more transwomen don't pass because of trying too hard, rather than not trying enough. I know this from experience. When I first went full time, I wore pink lipstick, eyeliner, eyeshadow and foundation every day for a while. Not only did this cause me to be late to school, but it actually hurt me in terms of passing. Wearing too much makeup will draw attention to you and possibly accentuate more masculine aspects of your face. It wasn't until I began getting tired of spending hours on makeup every day that I realized I actually looked softer, and more feminine with less or no makeup.
That being said, I think there is a happy medium. There are days I wear no makeup because of time constraints, but when I do, a little foundation, some eyeliner on the top of the eyelid and a bit of mascara does wonders for me (and using lip balm instead of gloss or lipstick). It helps me look fresher and more awake, yet it is subtle enough that it doesn't look overdone and retains the soft look that I aim for. I don't do this to pass, because I think I pass fine without makeup, but I do it because it is flattering and natural, and not overdone.
But to be honest, I would take no makeup than too much any day in terms of trying to look more feminine. Being confident in how you look without makeup is a lot better than feeling as though you have to rely on it. Makeup should accentuate your femininity, not be a crutch for it.