Christmas on the Upper East Side, According to Gossip Girl
By Alexus Mosley
There’s something about winter in New York that feels inherently Gossip Girl-coded. Maybe it’s the fact that the coats get better, the stakes get higher, and the cold sharpens everything. Or perhaps it’s just that the Upper East Side becomes a glittering stage of tradition, indulgence, and quiet competition. Christmas, especially, isn’t just a holiday in the world of Gossip Girl.
If the characters were celebrating the season in their own way, here’s exactly how Christmas would unfold.
Blair Waldorf’s Traditional and controlled Christmas
For Blair Waldorf, Christmas is sacred. It’s less about festivity and more about legacy. Her holiday season would revolve around perfectly preserved traditions, heirloom ornaments, gold-rimmed china, and a dining table that looks like it belongs in an Upper East Side penthouse passed down through generations.
Blair would host an intimate but meticulously planned Christmas dinner, where everything, from the seating chart to the dessert course, is intentional. Her outfit? A structured Christian coat, a tartan skirt, velvet accents, and of course, a headband. Christmas, in Blair’s world, is about elegance, order, and maintaining standards.
Serena van der Woodsen’s Escapist christmas
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Serena, on the other hand, treats Christmas as a feeling rather than a schedule. One year she’s in Aspen, the next she’s disappearing to St. Barts at the last minute. Her holidays are spontaneous, glamorous, and just a little chaotic.
Though she means well, she’ll probably forget a gift. Only to arrive glowing, wrapped in cashmere, champagne in hand, apologizing profusely. For Serena, Christmas is about freedom, warmth, and wherever the moment takes her.
Lily van der Woodsen’s Christmas as a form of Presentation
Lily’s Christmas is nothing short of museum-worthy. Her Upper East Side apartment would be transformed into a vision of seasonal perfection, towering trees, orchestral music drifting through the room, and guests dressed as though they’re attending a charity gala.
As the ultimate hostess, Lily ensures every detail reflects pedigree and polish. Christmas, for her, is about maintaining appearances and reinforcing social standing, a quiet reminder that elegance is always part of the family brand.
Chuck Bass’S Christmas as A Grand Gesture
Chuck Bass doesn’t do subtle, not even at Christmas. His idea of holiday cheer comes in the form of extravagant gifts, five-star hotel suites, and ungodly late-night rendezvous. Velvet blazers replace sweaters, and whiskey replaces eggnog.
He might seem emotionally distant for most of the evening, only to deliver an over-the-top gesture right before midnight. For Chuck, Christmas isn’t about tradition or warmth but is instead used as a subtle flex.
Nate Archibald’s Christmas as An Obligation
Nate’s Christmas is predictable but polished. Think country club brunches, polite conversations with donors, and family commitments that feel more ceremonial than celebratory. His holidays are rooted in duty, showing up, dressing appropriately, and doing what’s expected.
There’s comfort in the routine, even if it lacks excitement. Christmas, for Nate, is about responsibility and reputation.
Dan Humphrey’s meaningful Christmas
Dan spends Christmas in Brooklyn, browsing independent bookstores, exchanging modest gifts, and quietly judging the excess of the Upper East Side from afar. He romanticizes the season. It’s all poetry, Fitzgerald, and conversations about what Christmas should represent.
Of course, he can’t resist observing the UES festivities from a distance. For Dan, Christmas is about intention and not indulgence.
XOXO,