You know googling images, I think it's the print that is the barrier. That kind of floral (colors, scale, the kind of stylized linework) just hasn't yet come back in again since the 80's, which means it's probably due to, lol. If a dress was bleached white or dyed black it might have a chance of being prairie but capable of being styled in an edgy or boho way.
The last time I wore that kind of print was red roses on black cotton in strappy fit and flare sundress, which of course I wore with black stompy boots in the 90's.