Yeah, I spent about 3 years of being socially female (nights out with friends etc) as I felt more comfortable dressing in that way. Then I did the work thing as well when I 'officially' started my transition, which was about 1.5 years of doing name change stuff and, basically, being true to myself in the way I dressed, acted and the like.
So I started the HRT around 1.3 years ago, after around 4.5 years of a building transitional period. This wasn't intentional as an approach, it was just a natural progression that I suppose a lot of people do in secret but I just did it in a very open manner. There was a fair amount of going out in a female/non-binary way for years prior to my social transition, so it wasn't much of a surprise to those around me.
Never really had much of a negative experience from it; obviously there will always be some idiot in the street yelling things, but that's something that just happens regardless and is about their insecurity, not me....I look awesome!

Happens less these days, but then again I get clocked less as it's been a while. Not that I am, or have ever been, slavishly trying to 'pass', I've just been wearing clothes and presenting myself in a way that I'm comfortable and that makes me happy.
So, basically, the whole thing has been an evolution of myself and a very positive experience. I really think that doing it all in the open, from just being a 'guy who sometimes wears skirts', to being 'a guy who wears whatever he wants' and then everything beyond that has really limited the internal worry about what people will think, as I know because they are seeing the progression along with me. This is also useful because there wasn't ever any point that anyone had to deal with a huge leap between one gender and another.
It is, and always has been, my attitude that people need to spend significantly less time worrying about what other people think and just do what makes them feel happy. As long as it isn't actually bringing harm to other people or actually causing them issues (them not understanding doesn't count; they don't have to!) then just get on with it and sod anyone that has a problem with.
Not sure if that's what you were looking for as a response, but the TL;DR is that yes, I suppose I did. And it was ace.