The Worst ‘Gossip Girl’ Looks Of All Time

Everyone can agree that Gossip Girl is a show iconic for its fashion. From Serena’s sensual menswear looks to Blair’s classic plaid pieces and extravagant bows, each character has their own distinct personal style. Even lowly Joe—I mean, Dan Humphrey—has a very defined struggling-writer-hipster-wannabe-from-Brooklyn style of his own. However, even the greatest scripted show on television, with all its flawless fashion looks, couldn’t get it right every time. With rumors of a potential Gossip Girl reboot picking up steam (fingers crossed), let’s take a look back at some of the show’s greatest fashion crimes. Here are some of the worst Gossip Girl looks of all time.

Blair

Let’s start with Queen B. It’s easy to immediately declare that she can do no wrong; she was a princess, after all. Oh, but she can. She veryyyy much can. I mean, she did have a stint with Lonely Boy, can’t forgive her for that. But Blair has made some questionable fashion choices FOR SURE. I mean, personally I’m not here for her preppy blouses or childish bows, but it’s part of her look, so I’ll accept it. But what I won’t accept is this monstrosity. Okay Queen B, everyone knows you run the school. You got a lot of “yes” people. That being said, no one’s going to have the balls to tell you how horrific those banana yellow heels are, or yell at you for wearing mauve tights with open-toed shoes. The green coat isn’t good, and neither is a yellow shirt underneath it with gold accessories, but those shoes first and foremost are an abomination.

Serena

Look, I know we don’t always love our bridesmaid dresses, but I legit hate this. I mean, we all know Lily has always been not so low-key jealous of Serena. So really, it’s no shock that she would put her in her place with this terrible bridesmaid dress. I get the impression that she picked out this dress thinking it would be ugly af, but then saw Serena in it and was like, “Oh, f*ck! She still somehow looks good. Well, I’m not going to let her outshine me on my very special 5,000th wedding day! Okay, I’ll make her add these weird-ass black accessories to make her look real clownish.” Mission accomplished.

Jenny

I don’t know whose self-centered oblivious attitude annoys me more: Serena or Lil J. Like, I get it, Jenny. It DOES suck that you live in Brooklyn with Lonely Boy as a brother and Rufus, a wannabe rockstar with Peter Pan syndrome, as a father. Def not ideal. But your bratty and entitled behavior is beyond what you have earned for your unfortunate family. And this outfit is unforgivable. It’s the definition of Lil J constantly trying too hard. Like, you’re a pretty girl with an eye for fashion, and sweetie, you’re going to make it out of Brooklyn! Just chill. You don’t need two oversize T-shirts layered on top of each other, plus fishnets, plus the largest bag I’ve ever seen. You’re supposed to take off one thing before you leave the house, and Jenny could’ve take off four.

Vanessa

Oh, wait. You know how I just said I didn’t know who annoyed me more, Serena or Jenny? My b, forget that because Vanessa hands down takes the cake with the title of most annoying on Gossip Girl. It’s a shame because she’s stunning, yet is the definition of pesky. Between her self-righteous attitude and tacky discount store wardrobe, she is the absolute worst. For example, combo of a horrible statement necklace and baggy jeans stuffed into Converse with cartoons on them. It gives me all the cringe sweats. It looks like something you get on the JCPenney clearance rack in the curated “teen” section. It’s just doing too much, just like martyr Vanessa always does.

Chuck

I think almost any girl who’s watched Gossip Girl can admit that there is just something so inexplicably hot about Chuck Bass. Maybe it’s the self-confidence, the money, the power? Idk, but no matter how objectively hot Nate is, it’s Chuck’s true BDE that makes every girl wet. Explicit, but true. However, what doesn’t do it for me? Chuck’s double argyle with shorts and bow tie look. AND the socks are high socks. Just why? This is a look you’d see on a WASP-y dad at a golf course. I’m going to scream. 

Like I said, I’m praying that this isn’t just a rumor and that we really are getting a Gossip Girl reboot. I mean, considering no one can seem to come up with any original ideas anymore for scripted TV, I’m down for an attempted reboot. If you’ve been watching Riverdale this season then you know The CW is really reaching right now. Let’s just hope that they do it right, and not some corny knockoff version that makes us forget why we loved it in the first place.

Images: Getty (5)

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