Serena Van Der Woodson's Worst-Dressed Moments In Gossip Girl

Whether you love or hate "Gossip Girl," it is a time capsule of fashion in the mid-aughts, for better or worse. Leighton Meester's character, Blair Waldorf, had a pretty strict aesthetic that created some iconic fashion moments. One moment in particular included Waldorf wearing the absolute best outfit on "Gossip Girl." But, Blair's frenemy, Blake Lively's character Serena Van Der Woodsen, had a more chaotic style. It seems Serena might take after Blake, as Lively has a history of wearing inappropriate outfits while out and about or at red carpet events.   

Of course, Lively isn't the only person to blame for Serena's worst style moments; the "Gossip Girl" costume department would have to take some blame. In a 2022 interview with Vogue, Lively even credited the costume designer Eric Daman with opening her eyes to the fashion world and the important role a character's closet has in building their personality and the world around them. Serena not only had iconic hair but also had notable fashion moments. Here are some of Serena's biggest fashion disasters. 

Serena Van Der Woodson returns to New York City in Season 3 Episode 1 of "Gossip Girl," called "Reversals of Fortune." She'd been trying to lay low after an arrest, but soon realized "out of sight, out of mind" didn't work for her. She wore this gray-and-black-striped floor-length spaghetti-strap dress in a scene where she was having breakfast with her family.

It's fine to wear whatever you want at home, but it should probably fit. The dress didn't fit Lively around her chest area. While cleavage is a choice, it can still be unflattering, even in behind-the-scenes photos the dress looks frumpy.

This outfit from Season 2, Episode 11, "The Magnificent Archibalds" is described on-screen as a dress. But it's immediately confusing to look at because it appears to be an orange, high-waisted skirt and red blouse. Orange and red complement each other sometimes, so the dress alone is unique (though definitely a choice). But it's paired with a busy necklace that's overwhelming. 

Plus, she wears fishnets underneath it, which clashes with the fall vibe of the dress and moves it into goth territory. Serena is trying to impress a new boyfriend in the scene, but unsurprisingly, the relationship doesn't last.  

In a Season 6 episode titled "Save the Last Chance," Serena wore a lime green, blue, and white striped sweater with a pleated skirt to apologize to Blair for seducing Dan. It's surprising that Blair didn't kick her out for the offensive shade of lime green alone. Also, the outline of her bra doesn't work here. The zebra-striped bag clashes with the whole look, and her necklace seems uncomfortable. She should've kept the skirt and ditched everything else. 

The TikToker who added this outfit to their list of Serena's worst looks nailed it when they described this outfit as "so many patterns and in the worst way." The mixed patterns of the blazer, the top, and the tie are bad enough. But it's actually impossible to tell what she's wearing on her legs, let alone why or what episode it was in. Wool tights underneath boxers are a great guess. But whatever is going on in this episode, Serena has a fashion crisis that's stressful just to look at. 

In Season 5, Episode 7, Serena wore a white, fur-like vest over a white t-shirt with a reptile-like pattern, pairing it with a lightweight brown skirt and chunky heels. Even though it's small and likely just decorative, the vest is a weird contrast with such a light skirt. The shades of brown in her heels and her skirt also don't work well together, and the necklace makes the whole outfit too busy. But the fuzzy vest is the biggest offense. 

Blake Lively wore a bright green dress meant to sabotage in "Gossip Girl" Season 2 Episode 5, "The Serena Also Rises." Blair (Leighton Meester) achieved her goal by tricking Serena into wearing it at Blair's mother's fashion show because, while the color is jarring, the volume of the skirt is reminiscent of a diaper. Factor in her ratty looking hair, and the entire look was an absolute disaster. 

In Season 1, Episode 10, "Hi, Society," Serena wore a strapless gold evening gown to the debutante ball she was forced to attend. Ugly evening gowns are sad and rare, but this one was also totally impractical. The length meant she had to hold it up all night to walk, and the bunched fabric and floral applique made it seem heavy. Not to mention, the bow at the bust and random flowers made the dress busy and uglier.