Gossip Girl: The Valley, circa 2009

It feels like a lifetime ago — when Blair was on round two with Nate, Serena and Dan weren’t too annoying yet and there was the possibility of an 80s-themed Gossip Girl spin-off (which was thankfully nipped in the bud). The fashion was as dramatic as the storylines and just as rich as the real and fictional teens on Manhattan’s Upper East Side. Naturally, Serena was decked out in a $20,000 glistening chiffon halter gown by Christian Dior and Blair looked positively prom queen-majestic in a black and gold Marchesa corset creation — one-of-a-kind couture, of course.

{Photo: USWeekly via TVFanatic}