I think I would have to differentiate between the stuff I know is horribly unflattering on me or that I can't get a fit in, and looks that don't appeal to me.
My low arches and wide feet make it nearly impossible for me to wear or wear comfortably loafers, ballet flats, and slipper shoes; they would also not flatter my short, chunky legs. For the same reason wearing leggings would do no favors for my proportions, but it is also not a favorite look.
For some reason, I can't get my mind around tucking jeans in boots. It is difficult for me to do anyway due to fat legs, but I find the look fine on others! I can't for the life of me figure out why wearing boots in general doesn't appeal to me, but it certainly helps the budget to avoid boots. Could be that finding ones short enough is a hassle, and years ago my feet would get too hot in boots. Habit? My climate is not that cold, and I DO have rain boots that I have always coveted. Unfortunately, almost as soon as I bought them last fall, it stopped raining!
Slouchy looks on others are simply sloppy looks on me; that holds true for cardigans, too. I'm so glad that jackets have come back!!!
Knit dresses are another thing that looks great on others but dumpy on me. . . .
All these things I truly enjoy seeing in your WIWs. Instead of stylized models, it is great to see regular women (who may be plus, petite, or somewhere in-between!) and have a range of styles. So fun!!!