Hi AG!
Wow, your post made me feel quite complimented! I'm so glad my clothes look natural on me! And that I have a well defined style that evokes fairy tales! So thank you.
I didn't always dress the way I do now; it's only in the past 2-3 years I'd say that I've really narrowed down on my style & embraced my urchinness/etc. Before that, I kind of struggled against my youthful looks and cuteness; after all, being cute is the opposite of being powerful, yes? So I had a bit of a mishmash closet full of all kinds of styles of clothes, because I hadn't quite figured out what my style was yet. And I wished that I had a curvy, voluptuous, plump figure, not because of men but because I thought all of those curves were just so lovely looking. Oh and I wanted to have high contrast, Snow White colouring with super pale skin and thick dark hair cascading over said curves. Or maybe be a red head (I actually did dye my hair red for awhile but it got so dried out and the red would fade every month it drove me nuts). Anyway, eventually I realised I wasn't going to grow anymore and that I might as well embrace my figure for what it was good at and my colouring for what made it glow. And along the way, I started to narrow down things that fit my personality as well as my body, and then I found YLF which sent me down a rabbit hole of 'find your style' blogs that gave me the tools to analyse my preferences and find patterns to help me figure out what clothes to buy. So my style and love for/acceptace of my physical features kind of grew together. I guess I just got lucky that my inner fantasy life (which is ridiculously vivid, lol) doesn't require a different body type: I can walk through the woods on my short legs just as well. And my slimness would fit right in at a Victorian orphanage. I believe that if I was curvy and/or high contrast, I would have just gravitated to a different version of my style persona/inner fantasy, because I find several curvy/plus size bloggers very inspirational, but of course I can't know for sure. As it is, I figured out a few formulas that make me happy and just play with them.
I also recognise that apart from my small bust and my naturally dark blonde-ish aka mousey hair (I *hate* the phrase dishwater blonde), I have a completely socially sanctioned body/face, which made the acceptance process much easier; I benefit from white and thin privilege, as much as I wish neither existed. When I watch movies or TV shows and feel inspired by what actresses are wearing (and I was very inspired by Ginnifer Goodwin in season one of Once Upon a Time, which aired just about the time I began coalescing my style), they're often a similar build to my own, which definitely makes things easier too. And of course I don't work in an office, so I don't have to dress to please anyone but myself most of the time!
I feel my style and physical appearance are much cuter and almost more vulnerable in a sense than my personality. I have a strong personality, with strong convictions, and ever since I was little I've been willing to stand up for myself and believed in myself. I was a shark in debate in high school; my coach had to tell me to tone it down so I didn't make other debaters cry. I'm not sure that's the first thing strangers would think when they saw me: there's a woman who knows her own mind and will speak it regardless. But luckily, it doesn't take very long in the getting to know me process for them to figure it out!
There's only so much I can do to counteract the baby face impression, so instead I try to emphasise my bookishness and attention to detail and curiousity about the world in my outfits, as those are all real aspects of my personality too.
I've rambled on for ages now & I'm not sure I've answered your questions! I hope I have though, if not feel free to ask me more. For what it's worth, I think you do an excellent job of dressing UWP, and in photos at least you never seem to be lacking in stature. And I *loved* reading everyone's responses to this thread, so way to go you for starting it!