My wife used to tell me that shoes were accessories. She chose the shoes that matched or accented the outfit she was wearing. Women’s shoes don’t have to have high heels to look feminine. In her more mature years, she would often wear very girly styles with kitten heels and look smashingly sexy. She often told me that she would leave wearing higher stilettos to me because she found them to be uncomfortable. As for me, I love wearing heels. In my. 30’s and 40’s my normal shoes had 5” heels and I enjoyed occasionally wearing higher heels. Now that I’m enjoying my 60’s, I very rarely wear heels higher than 4” anymore. My main interest has always been “Girls Shoes”, not looking like a girl.
But, back on point, you’re evolutionary process is probably normal. Transitioning from pure male appearance to a male wearing female garments in public has elements of your being comfortable at the same time as your overcoming your apprehension about your appearance not being acceptable. It’s a long process. Being a female is a complex process. There is a lot more to think about, especially if you want to appear only slightly feminine. One step at a time!