Liesbeth, lol at "a frazzled career woman in a nineties comedy, stranded in a small town where I'm first mocked by but then fall in love with the local woodworker." I know this feeling all too well and it's probably why 99% of my outfits are hardly outfits at all. If I dress even a little bit "up" from my milieu, I start to feel self-conscious like that 90s rom-com character, wiping mud off her good shoes or getting her coat caught on a barbed wire fence or something. I mostly want my clothes not to get in the way, and nice things often get in the way just by being nice.
I've found a lot of value in posting not-great outfits (I share pretty much anything I manage to get a picture of) simply as a frame of reference and to document evolution, or something. And I also enjoy reading others' "keeping it real" posts; way more interesting to me to see what people reach for when they're not trying, not planning, just living their lives. At least in my case, sometimes my "meh" things feel more "me" than many sharp, spiffy things out there, especially this year.