Turns out,Leighton Meester’sBlair wasn’t always the fashion icon she eventually became.

The two characters were simultaneously best friends and fierce rivals.

That said, our favorite headband-wearing shopaholic didn’t always nail her looks.

Blair Waldorf In Gossip Girl

Somehow, this cameo was overshadowed by Blair’s highly questionable outfit choice.

Remember the stunningblue dressshe wore to marry Chuck?

Blair Waldorf On Gossip Girl