Top 10 Worst Gossip Girl Looks Of All Time

Earlier in this episode we got to see Blair try on several potential dresses for brunch. Maybe not show stopping, but any of them would have been an improvement over her final choice. In a rare misstep for Queen B, she settles on an ensemble that could charitably be called conflicted. Her 60’s inspired white eyelet lace dress is pretty enough, if a little prissy. However, she pairs it with a set of black lace tights, and the two pieces just don’t work together. The black looks too stark with the white. The different lace patterns are aggressively mismatched. The dress seems more suited for spring or summer, while the tights are definitely fall/winter. Cleary B’s personal life was so distracting she forgot to check a mirror.

Serena definitely embraced a more free-spirited style throughout the series. Her boho game was usually strong, but when she flopped it was hard not to notice. Like when she showed up for brunch in this white dress with its floral details. Not only does it look too casual for the event, but it actually kind of reminds us more of a fancy slip rather than an actual dress, especially with the drawstring waist. The flowers should lend it a sweet, spring-time vibe, but instead they just give the whole thing a bargain store quality. Which is pretty unforgivable considering that similar pieces by the designer, Bluemarine, retail for over $1,000. Not even Serena’s stunning styling can save this one.

We don’t know if this look is worse for Vanessa, who wore it, or Jenny, who designed it. Vanessa looks great in the vibrant orange color, and we even love the pops of turquoise in her accessories, but the dress is just tragic. The wing-like sleeves are definitely odd, and the highlighter yellow crinoline doesn’t go with the dress in terms of either color or style. The fabric also looks kind of chintzy, which is not helped by the gathering at the bust. And while Blair had a fake flower in her hair too, the one sported by Vanessa just looks sad. The whole outfit comes off looking like a school home ec project, not the work of a talented wunderkind designer.

Blair can take things too far sometimes. This goes for every aspect of her life, including her fashion choices. This look is a prime example. The bright red tights under her shorts are the first element to jump out. However, the more you look, the worse this outfit gets, and none of it really seems to belong together. The navy shorts and sweater top, with its ribbon belt, aren’t great to begin with. Then the ruffled shirt and black necktie, and the tights and striped blazer respectively all look like pieces of different ensembles smashed together. It all adds up to a messy, unfocused, and weirdly juvenile look that strikes us as out of character for the usually polished Blair.

As the show progressed we got so used to seeing Chuck in his endless series of impeccable suits we forgot that he wasn’t always immune to fashion faux pas. During the Season 2 opener, though, we get a reminder of Chuck’s checkered style past. Literally. It’s hard to find khaki shorts offensive, but when paired with this red, beige, and cream sweater vest they become insufferable. And we can’t forget the plaid bow tie, of course. However, what really takes this look over the top are the argyle kneesocks. Not only are they, well, kneesocks, but the burgundy color doesn’t go with any other part of the outfit. Thankfully the scene is brief and we don’t have to look at it for long.

Vanessa had some of the most contentious style on “Gossip Girl,” and looks like this are a perfect example of why. Her red plaid blouse is perfect for a Thanksgiving dinner, however, her cropped technicolor jacket is pretty egregious. For one thing, the use of Navajo print is so on the nose that it circles back around to clueless. It’s almost as painful as the way it clashes plaid. The bottom half of the outfit doesn’t help matters. Vanessa’s grey heathered leggings ultimately end up looking like athletic wear, while the slouchy suede booties create an odd contrast with the rest of the color palette. Thanksgiving is a day for gratitude, but looking at this ensemble we have nothing but regrets.

Is there anything money can’t buy? As seen on “Gossip Girl,” apparently it’s a decent bridesmaid’s dress. The color and floral print of the one Serena wears for her mother’s wedding could be nice, but the design does it no favors. For one thing, the high, frilly collar looks fussy and claustrophobic, and the tiered skirt gives a bit of a lampshade effect. Then there’s the black accents, which are harsh against the softer yellow of the dress. Don’t even get us started on those ridiculous glovelets. Plus, the plunging keyhole neckline seems kind of inappropriate for a 17-year-old girl. Most ugly bridesmaids dresses are meant to keep the focus on the bride, but this one is kind of like a train wreck. It’s impossible to look away.

Oh, B...where to begin with this one. There’s a great 1920s reference happening with the shoes and the cloche, but the whole look is giving us a jazz age hangover. The turquoise plaid skirt could be cute in a different ensemble. Here the shared turquoise of the skirt and top can’t change the fact that the patterns don’t work together, and the black and white in the blouse are at odds with the brown in the skirt. To add insult to injury, the fit of the top is unflattering. Then there’s the odd skinny scarf, and the fact that the hat doesn’t match anything else...We never thought we’d use the word dowdy to describe Blair, but here we are.

Jenny always struggled between her Brooklyn roots and her Upper East Side ambitions. Once she became Queen of Constance she practically developed a split personality. In late Season 3 the conflict finally manifested externally. Fishnets with a lace mini skirt seem like a little much for school, for one thing. It is consistent with the rocker edge Jenny brought to the Met steps though. It’s the top half that’s really bizarre. With the baggy layered t-shirts and the loose tie something about it feels very walk of shame. Or at the very least, very laundry day. Half punk, half grunge, even Constance’s loose dress code would have to call foul on this look, right? Talk about the best of no world.

Before we unveil our top pick, here are a few honorable mentions.

Serena’s Attempt to Play the Part of Serious Student, “The Townie”
A Look As Confused As Serena’s Academic Pursuits in General

Not Quite Skating By, “Roman Holiday”
Blair’s Behavior Might Be Immature, But Her Outfit is Downright Childish

Pink Peril, “Much ‘I Do’ About Nothing”
A Baggy Shape and a Bubble Hem? We Say a Resounding “I Don’t.”

Chuck Bass is many things, but a jock never seemed to be one of them. During his Lost Weekend in Season 1 we understand why. Chuck rolls up to the basketball court in an outfit that could only be described as laughable. Is it the fact that his shoes are coordinated with his shorts? Is it the eye-roll-inducing flex that is the crown print on his shirt? Personally, for us it’s the matching head and wristbands that get us snorting. But maybe it’s a rich kid thing, right? Yeah, except for the fact that Chuck is the only one dressed up this way. As tough as Chuck wants to appear, it’s just impossible to take him seriously in this look.