I posted a few weeks ago how I wore black swede boots with a 2 1/2" tapered heel under long black boot cut jeans in the mall and was clocked by half the people I passed. Yesterday was raining and I went shopping to several department stores, same jeans and black windbreaker but wore 2" black ankle boots that were mostly covered by the long black jeans. Being rainy and gloomy and with lower heels I thought surely I would blend. In all of the stores I could see the quick keen eye of women glancing down at my boots, some then gave me a nice smile as if to say you are wearing women's boots but I'm just fine with that. Others did their quick look and then just went back to what they were doing. Some even noticed when I was walking toward them and couldn't see the heel. After a lot of being clocked I began to feel very comfortable with them noticing and had the feeling of their being O.K. with this and them surmising a part of me was female and wanted to dress partially female just like them. In Other Words I had left the all male team and had come over to the female side because a part of me enjoyed what being female had to offer. We both enjoy and appreciate dressing as a woman to what ever degree, same as the way some women dress like men (sloppy, tee shirts, jeans, flip flops, no makeup, short hair). This has given me a whole new vision and confidence that it's perfectly O.K. to wear some more stylish and attractive female items of clothing that aren't offered for men. Could this be Male to Female Crossdressing or just dressing in the clothes you like just as women have done wearing men's clothing for a long, long time
And yes this has been said on this site before, have confidence and wear what you want.