Totally agree.I see it as a get-up or a series of costumes. She's a D-list celebrity (and I don't mean that as a diss - that's just what her status level in the entertainmengt industry is), and this aesthetic is part of her persona. If she had never gotten into entertainment and just worked in an office somewhere in Chicago she'd probably be dressed normal.
But to answer your question, I'd never ever want to date a woman who dressed like this (in earnest).