Blair's guilty of making a fashion faux-pas on more than one occasion, but her worst one has to be this ensemble. In season two, episode 10, Blair Waldorf tries to sabotage her mother's new relationship with Cyrus Rose, played by Wallace Shawn. In an attempt to win Blair over, Cyrus gets his old friend Cyndi Lauper to perform at her 18th birthday party. Somehow, this cameo was overshadowed by Blair's highly questionable outfit choice.
Throughout the series, Blair graced our screens wearing some of the most awe-inspiring looks that remain unmatched to this day. Remember the stunning blue dress she wore to marry Chuck? Iconic. But the overpowering white ruffled shirt paired with a black mini skirt she wore for the celebration of her most important birthday to date? A huge letdown.
The shirt takes over her frame and looks downright uncomfortable, and the short hemline of the skirt, while a popular look at the time, makes the outfit look extremely unbalanced. Blair wow-ed at nearly every major event she attended, which makes us wonder just how she missed the mark so badly on this occasion.
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