This is a really interesting conversation! I think I really resonate with what Shevia said. Like her, I think my #1 goal with style is to be interesting (both to myself and to others). I don't want to look like everyone else, but on the other hand of course I still have certain figure flattery priorities and hangups that I take into account. For example, I always try to minimize the appearance of my extremely short waist, and I don't wear things that make my butt appear even bigger than it already is! On the other hand, I have a nicely defined waist but I don't really care to always define it and I'll wear waist surrendering things with aplomb.
I also have a strong contrarian streak. I cannot tell you how many times I have been told that I should wear more bombshell things, or that I look great in hourglass silhouettes, etc. All that praise/encouragement actually makes me even less likely to want to dress in those silhouettes. (I already am inclined against them because I have a pretty knee-jerk response to being thought of as conventionally "sexy".) I'm not saying that I dress to hide my hourglass shape necessarily, but I do not want to accentuate it.
The concept of JFE is such a freeing thing for me. And for the record, I'd wear your coat with two changes, both having to do more with poison eye/personal issues rather than flattery. (The bracelet sleeves, as you know, and the fur, because I have weird tactile issues with fur.)
ETA: Also, I think we can't discount the grass-is-always-greener argument. I HAVE the conventional hourglass figure and I can't tell you how often I've wished for the IT, avant garde figure. But I think this is just a case of always wanting what you can't have, you know? We just have to accept that not everything will work for everyone, because people come in all sorts of shapes and sizes. I think at its heart JFE is about figuring out how to make the things we like work for the bodies we have.