Waldorf, for example, didn’t stop dressing for her inner child every Thanksgiving, no matter how many unique girl plans and complexes exploded at the table. In Season 3, we see her sporting this gorgeous brocade dress while getting angry at her mother for her supposed pregnancy while Jason Derulo’s “Whatcha Say” plays in the background (the latter detail is key to this scene , I promise). In season 4, she is about to fly to Paris to visit her father wearing an orange plaid dress and sheer black tights when she derails to see her best friend Serena in rehab. Every year, she’s there, dressed with the best of intentions to celebrate her favorite holiday, including references to kids’ clothes that look chic for a twenty-something. Even if she should know better by now, why waste an opportunity to create an incredibly impossible fantasy? Or even dress for it?
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