I love this dress from Holly at Lucite Box. This falls into the "It's so obvious, it must be ironic!" category — don't you think?
I can see it worn that way — ironic Brooklyn hipster style — with a long fuzzy sweater and flats, or (heaven forfend) those slouchy elf boots that have inexplicably returned from the dead. Or you could rock it straight-up with classic stiletto heels and big hoop earrings.
To modernize it, you'd have to wear those (also largely inexplicable) open-toe wedge-heel booties that I see everywhere and a Balmain shoulder (unless the Balmain shoulder is already out? I can't keep track).
If this is your size, I'd jump on it — it's a great holiday-party dress and it's only $85!