So Nostalgic
17 Years Ago, Serena Van Der Woodsen Wore Her Most NSFW ‘Fit Ever
This was probably the most inappropriate look out of Gossip Girl’s entire run.
Justice for Blair Waldorf! On Gossip Girl, Queen B’s lifelong dream was to attend Yale, like her dad did. While she had to apply and prep like every other applicant, her best frenemy, Serena van der Woodsen, was personally invited by the dean to visit the campus. In true Serena form, she accepted the invite in a last-minute attempt to spite her so-called BFF — and wore something utterly risqué and NSFW in the process.
Serena’s Cleavage-Baring Top
The second season of the CW show aired in the fall of 2008 and followed the Constance Billard students as they prepped for college. Though Serena initially planned on attending Brown, in Episode 6, “New Haven Can Wait,” she decided to go to Yale after a fight with Blair. As the Upper East Side’s Golden Girl, Serena always charmed whomever she came across. By the time her interview was over, the dean was in stitches and thoroughly impressed.
Though her interview was seemingly A+, her outfit was, well... not. For one, she wore jeans, aka the epitome of casual. As any interviewee knows, denims are a dress code no-no.
She committed another (and even bigger) fashion sin with her top: a white blouse with a plunging neckline so deep, it slid down her ribs. While baring décolletage was practically a staple Serena move on the show, given the situation, it was completely NSFW (or, in this case, NSFS — Not Safe For School).
These days, style icons are way more dress code-resistant, chicly turning officewear spicy with the corp sleaze trend. But even the most risk-taking fashion savants would likely think twice about flaunting cleavage during a college interview — even one who wore their graduation tassel in their hair.
She paired the look with more questionable style choices for her meeting, including knee-high boots. But hey, at least she wore a blazer.
Blair Wore The Polar Opposite
Proving that things come easily for S, the inappropriate outfit didn’t deter her application (and neither did the fact that she physically threw hands with B at the dean’s private gathering later in the episode). Serena was even guaranteed early acceptance if she agreed to a press release.
Meanwhile, Blair, who was appropriately dressed, didn’t get in early. At least she looked chic. Ever the preppy stylista, she wore a button-down accessorized with a necktie, one of the buzziest trends in 2025.
She layered her top under an olive sweater, completely fastened, and paired it with a darker fir green pencil skirt. Even her footwear was business-inspired: heeled lace-up pumps.
Sorry, Serena. But based on outfits alone, Blair should’ve gotten Yale.
