When the Cheezburger Network first exploded all over the Net, a couple of dozen sub-sites appeared, one of them called Poorly Dressed, which might be considered a godmother to People of Wal-Mart. The poorlydressed.com domain seems to have passed to new owners since then, but some of the pictures were memorable, if only because they were so horrible.
Then there’s the one picture I kept from those days, and frankly, I’d substitute “cleverly” for “poorly”:
This borders on trompe l’oeil. In fact, it could possibly trompe both les yeux.