16 Years Ago, Serena Van Der Woodsen Wore Her Worst Gossip Girl Look

Hey, Upper East Siders. It’s been over a decade since we officially said goodbye to our favorite Gossip Girl blonde, but her fashion lives on forever. Particularly, those that haunt us. And just like your favorite anonymous *coughs-Dan Humphrey-coughs* blogger, I’ve got receipts.

Serena van der Woodsen was, incomparably, the golden girl of the UES. But while everyone swooned over her — boys, designers, and even college deans — her romantic and personal choices were often messy. Still, regardless of whatever mess she created — whether she was riding away on a stolen horse to get Daddy van der Woodsen’s attention or having an affair with a married congressman — she always looked flawless. Well, except for one ensemble that was arguably her most chaotic look — and likely purposefully so. I’m talking about her Thanksgiving ‘fit from the Season 1 episode “Blair Waldorf Must Pie,” the best Thanksgiving episode of all time, IMHO.

The 2007 episode began with a Dan (Penn Badgley) flashback to the holiday a year prior: The old Serena (Blake Lively) walked out of a bar blitzed, while Blair (Leighton Meester) scrambled to help her get home. But with Blair preoccupied, Serena crossed the street and almost got hit by a car until Dan appeared and saved her from her near accident. He took the opportunity to introduce himself, but Blair swooped in to grab her BFF, leaving him Serena-less and pie-less. Sorry, Lonely Boy.

While all this chaos ensued, the typically impeccably dressed Serena looked equally frenzied sartorially. She wore a green V-neck dress that looked so frumpy and out of place in her archive of luxe and decadent dresses that viewers were so used to her wearing. Who bought it? Unclear. Because Lily Rhodes/van der Woodsen/Bass/Humphrey would never. She then topped it off with a leopard print coat that was so ill-fitting and out of character that it looked like she picked it up from the bar she just stepped out of (which she has done elsewhere in the series).

Even her black tights, blue/gray booties, and earrings felt so haphazardly strewn together. Not to mention her hair — her always perfectly tousled lengths were just... messy.

This scene was actually when Serena and Dan *officially* met — or, at least, it’s the first time Dan actually introduced himself, marking a major milestone for the endgame couple. (The pair famously interacted at a party prior but Serena mistook him for someone else.) Unfortunately, Serena wouldn’t remember him, nor the interaction.

I, on the other hand, will always remember the outfit.