I used to tread what I considered a borderline, wearing slides with 2" heels, a woman's top and jeans...even a bit of make up. I know that some folks looked at me as being an effeminate or metrosexual, but maybe that' was an appropriate characterization, and frankly, it certainly didn't hurt anyone. Now, I'm more comfortable going full femme, but I can't bring myself to go without makeup. I just feel like I have to do something to soften my more masculine features when I go out.
I can understand the frustration with makeup, particularly when your vision is a problem.