Interesting questions, rachylou. I didn't post some truly horrid pictures from the early days where my shirts were clearly too short, not to mention my jeans. I think that was step zero, and getting fits reasonably right - most things were either too loose or too tight. And I was wearing the wrong size bra. Taking pictures helped a lot with lengths and proportions because it's not something you'd necessarily notice when you're looking at yourself in the mirror. Even in a full-length mirror I think most of us tend to look waist-up and not at the whole picture.
As I went through all my pictures trying to pick out the ones I wanted to share, it made me realize that my most successful outfits, at least in photos, are not particularly edgy or new. Some silhouettes work on me and lots don't; some colors work on me and some don't. So my personal interest to have fun with fashion actually clashes with my desire to look good.
I think that's what Thistle was getting at with her backsliding thread, too. A lot of us know what basic things flatter us, but often we're lead astray by the search for newness. How do you balance that with staying reasonably up to date and looking current? Now there's the $64k question.