Oh Thistle, big hugs. You may not expect it, but I know exactly what you mean. I've actually got another perspective to add too.
Most of my friends would probably describe me as pretty fashion savvy and I would say that most of them would have said that all the way back into my 20s (I'm *ahem* not near my 20s now). At least as far as small town fashion went in the '90s.
All through middle school and high school I was completely and utterly clueless about fashion. It wasn't that I didn't want to know about it. I just didn't have anyone to teach me and I had no money at all to spend on clothes. In retrospect, I think a lot of the gals who dressed so well back then, the gals with innate fashion sense, were actually young women whose mothers knew about it and who had disposable income to spend on clothes. I think that that's how some women get a head start. No judgment in that, just an observation (and maybe a little wish that I'd had that help too.)
Like you, I struggled and scrabbled for every little bit of knowledge that finally came together for me. I probably started earlier, but I didn't have anything as amazing as this forum to help me learn things either. It just takes time. And you've got an instruction book and a cheer leading section all wrapped up in one in YLF. I bet next year, when you look back on this, your head is going to spin when you think about how much you've learned and how far you've come. I bet it already is! I'm nearing my one year point and mine certainly is!
(And I really hope that Suz weighs in on this because I think she probably knows exactly what you mean and you'd never guess it to look at the fabulous fashionista that she is now!)