I have been going out of my house in obvious female clothes for several years now, including sometimes working in the front yard with a skirt on. Numerous people in the neighbourhood have seen me for sure, and there has never been a problem. I have not been hiding it at all.
But it has always happened that one of my two immediate next door neighbours has not been out at the same time I was. Years of my wondering whether they had possibly seen me while happening to look out the side of their front window (which is draped.)
Well, Thursday night, my neighbour just happened to be getting things out of his car (parked at the street) at the same time that I arrived back after walking home from a local deli. And I wasn't just wearing a plain denim skirt this time: I was wearing a beige linen dress. I was probably not recognizable in the distance at the time I caught sight of him, so I could maybe have hidden... but why? And it would have looked strange to have someone duck out of sight. So I gave a mental smile and an amused snort, and walked right up and said hello, and I asked about his prized Mustang. He gave no indication that he noticed anything different. Which probably implies that Yes, they saw me long ago and have adapted by now.
Let's see... the neighbours two doors over only moved in a month ago so I haven't met them yet. But now everyone in a two-house radius (including across the back alley) has seen for sure. No known problems. Including no problem at all from the redneck couple.