This article was written by The Zillennial Zine’s senior fall editorial intern Lauren Sanchez. Find her on Instagram at @lauren.sanchezz. If you would like to share an article with The Zillennial, send us an email at thezillennialzine@gmail.com.
Thanksgiving: it’s the one day we all gather around the table, indulge in pumpkin pie, and try our best to survive the questions, the family drama, and, of course, the endless second helpings. While the holiday season can be anything but stress-free – cue the “Where’s your plus-one?” and “What are your plans for the future?” conversations – the one thing you shouldn’t have to stress about is your outfit. And that’s where our favorite Upper East Siders come in to save the day!
After all, the Gossip Girl Thanksgiving episodes were practically cinematic legends – no one does holiday drama better. Between Blair’s iconic monologues, Serena’s surprise entrances, and that one unforgettable dinner scene (you know the one), Thanksgiving was always the Upper East Side’s most stylish battlefield. And now, you can bring a little of that polished chaos to your own Turkey Day table.
So whether you’re channeling Blair’s perfectly preppy look, Serena’s effortlessly chic vibe or even Chuck’s undeniable sophistication, we’ve curated the ultimate Thanksgiving wardrobe based on the style of your favorite Gossip Girl character. After all, there’s only one thing we know for sure: you’re never fully dressed without a little drama!
Queen B – Blair Waldorf
Starting with my favorite character from the show, when it comes to Thanksgiving style, Blair Waldorf wouldn’t settle for anything less than picture-perfect elegance. I mean, hello! They don’t call Blair “Queen B” for nothing. To channel her preppy sophistication, opt for a chic tweed mini dress in a rich fall hue and pair it with a cropped, double-breasted blazer to keep things sharp and polished to ensure you exude her Queen B confidence. For footwear, go for sheer tights and either classic-heeled Mary Janes or sleek velvet ballet flats, perfect for a Thanksgiving dinner. And of course, no Blair look is complete without her signature headband!
The It Girl – Serena van der Woodsen
Serena van der Woodsen, the “golden girl” of the show. Although she does have a few questionable looks from the show, her laid-back yet chic take on fashion makes her one of the most fashionable icons in all of the UES. For a modern take on her Thanksgiving style, go for a sleek satin midi dress in a warm, fall-inspired hue like burnt orange or deep burgundy. Add an oversized cardigan for that relaxed, yet polished vibe Serena does so well. Pair it with tall suede boots to balance out the softness of the dress with a touch of edge.
“I’m Chuck Bass.” Enough said.
Hearing those words alone is enough to understand the level of charisma and power Chuck brings to any room, and when it comes to Thanksgiving style, Chuck’s look is all about luxe, sharp tailoring and a bit of drama. For a Thanksgiving look that channels Chuck Bass’s sharp, sophisticated style, we recommend starting with a tailored, structured blazer or coat in rich, autumnal shades like deep burgundy, navy, or charcoal. It’s the perfect way to bring a bit of that high-powered elegance to the table! Underneath, layer a cashmere turtleneck for a sleek, modern edge and pair it with a high-waisted midi skirt in a statement fabric like velvet or wool. To complete the look, pick out opaque tights and heeled boots to add that signature polish!
The One Who Serena Should’ve Ended Up With (Nate Archibald)
Nate Archibald’s style always leans toward that classic, preppy aesthetic with just the right amount of refined elegance. Start with a fitted, wool blazer in a classic plaid pattern for that Ivy League vibe. Underneath, layer a crisp, button-down shirt in white or light blue, and add a cashmere sweater vest or cardigan. For the bottoms, go for high-waisted, tailored trousers or a pleated skirt in a neutral tone like camel or navy to keep the ensemble chic but comfortable!
Lonely Boy – Dan Humphrey
For an outfit that channels Dan Humphrey’s effortlessly cool, Brooklyn-inspired style, begin with a soft, oversized knit sweater in a neutral tone – like warm beige, charcoal or even a deep burgundy. Pair it with a high-waisted midi skirt in a sleek material. For accessories, keep it minimal like a delicate chain necklace and a few understated rings will add to the subtle, laid-back cool that Dan always has.
Little J – Jenny Humphrey
Little J’s style is all about mixing youthful rebellion with high fashion. Her rebellious attitude and fearless fashion choices are the perfect fit for anyone who wants to avoid the predictable family conversations at holiday gatherings and instead let their outfit do all the talking. For a Jenny-inspired look, consider a form-fitting leather jacket in black or deep brown to channel her edgy, punk aesthetic. For bottoms, a mini skirt or tailored high-waisted trousers – think plaid or houndstooth – to give the outfit that downtown, yet bold vibe Jenny’s known for.
My Fave UES Mom – Lily van der Woodsen
Lily van der Woodsen’s style is the epitome of sophisticated luxury. Incredibly polished and elegant, any outfit inspiration for her needs to exude that! Definitely consider wearing a tailored, structured wool/cashmere coat. Underneath, wear a silk blouse or fitted sweater in a soft tone, paired with high-waisted trousers or a midi skirt in a complementary shade and pair it with pointed-toe pumps or ankle boots to elevate the look, adding just the right amount of height and polish. If you want to look poised and never overdone, Lily van der Woodesen should be your go-to outfit inspo this holiday.
No matter which Gossip Girl character you resonate with, one thing is clear: these iconic Upper East Side styles offer the perfect inspiration that will make you feel like you’re walking straight out of the show on Thanksgiving. Whether you’re channeling Blair’s elegance, Serena’s effortless glamour or Jenny’s rebellious edge, there’s an outfit that fits who you are! And with that, XOXO, you’re ready to take on the holiday, Gossip Girl style.
What do you think of our Thanksgiving Gossip Girl outfit inspo? Who’s your favorite from the show? Let us know in the comments below!
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