Hey Upper East Coasters, Gossip Girl’s protégé here, with the scoop of the Top Ten BEST and WORST outfits on your favorite show’s favorite show, Gossip Girl.

And no, to the three fans who like it, I will not be including the flop that was the 2021 remake of the hit show. It was good, I’ll admit, but it had more of Netflix’s Elite vibe than it did Gossip Girl.

So without further ado, queue “Young Folks” by Peter Bjorn and John, grab a bone-dry cappuccino, and let us begin.

The Best of the Best

1. Serena van der Woodsen’s Iconic First Episode Look

Every girl knows there’s no better fashion statement black tall boots with dark skinny jeans and an oversized handbag to accentuate your look, especially during the fall season.

Here, Blake Lively’s character Serena van der Woodsen wears a Duarte and Jeans jacket in the first episode as she makes her return back to the Upper East Side after mysteriously leaving six months prior for boarding school in Connecticut. S (as the show has affectionately nicknamed her) and her one-and-only jacket is a staple piece for any city girl in the fall.

Serena van der Woodsen’s first episode look is an iconic one that has left fans scouring every possible online source to find it. It’s a kind of look that, as casual as it is, makes a statement in every single way, a casual statement trying to disguise her sudden return. Yet it can’t hide her from the eyes of everyone–from friends’ boyfriends to the online gossip website “Gossip Girl.”

2. Blair Waldorf’s Classy White Party Dress

What better way than to end a scandalous summer in the Hamptons than with an invitation to the White Party, a new British beau, and the perfect Snow White dress to contradict everything–and everyone–you’ve done this summer? No one knows fashion better than Blair Waldorf, played by Leighton Meester, so it comes to no surprise that B (Meester’s character’s nickname in the show, same as Lively) is decked out in a scalloped Marc Jacobs dress with the perfect pumps and headband to match. 

3. Chuck Bass and his ICONIC J. Press Scarf

While S and B may be the queens of fashion on the Upper East Side, taking the cake for the king of fashion is none other than Chuck Bass himself. Chuck’s J. Press scarf, which plays a major role in the iconic and feminine side of the dark character, is a staple piece in both fall and winter fashion throughout the show.  Some might even call him a diva for his trademark scarf. Usually decked out in expensive suits or all-black attire, Chuck’s scarf adds another layer to his character, which proves that he is not just the shallow playboy he was written to be.

4. Jenny Humphrey’s Cotillion Dress 

Now, before you all crucify me for this take and call me a fake Gossip Girl fan, hear me out. Jenny, as problematic as she is, did have some major fashion serves throughout the show, specifically in Seasons 1 and 3 (after she went emo and made a huge comeback). Her gorgeous Blumarine dress gives her a sleek and elegant look which flows elegantly on her physique. Not to mention, those gorgeous heels she wears to top her look off is what ties the beauty of her outfit all together. 

5. Lily van der Woodsen’s Street Style

Never without a Birkin or Cartier bag in hand, the creme de la creme of fashion, Lily van der Woodsen’s elegant yet iconic street style consists of tight dark wash jeans (much like what her daughter wears), heels, and a trench coat to match. Lily also pairs almost all of her outfits with a French twist or low bun, occasionally opting for her hair down. Her wardrobe primarily consists of colors like beige, cream, soft browns and grays, and some touches of whites and blacks here and there.

Belonging to such an elite social class on the Upper East Side means Lily can’t have much of a personality, which is therefore reflected in her fashion choices. However, you will see her add a touch of blue or pink in some of her outfits, proving that even those with the most bland and neutral exterior aren’t always what hides beneath the surface. That can be interpreted many ways.

And Now, For The Worst Of The Worst:

Here are the top five WORST outfits on Gossip Girl. Yes, Vanessa Abrams will take up half of this list. Yes, Serena van der Woodsen will also take up half of this list. Yes, I will only be including one of Blair Waldorf’s outfits in Season 6 where she was done ridiculously dirty.

1. Vanessa Abrams’ Style In General Because It’s All the Same Thing. Sorry Not Sorry. 

Now, I’d like to preface this by saying I think Jessica Szohr is absolutely stunning and an amazing actress. That being said, I know for a fact she must have been fuming over the way her character Vanessa Abrams was dressed on Gossip Girl. I know they were trying to make her fit into this “boho sustainable hippie 2010s Brooklyn girl,” but seriously? Her outfits consist of clashing floral patterns with a fringe bag, layered necklaces, and a pair of chunky heels. 

I know Vanessa was a problematic character, but even Georgina Sparks who played the “on-and-off” villain was dressed and styled better than her. I’d also like to point out that Vanessa stands as the only person of color in the main cast of Gossip Girl. Being a show that was made in the early 2000s, it has a HUGE lack of diversity. Vanessa’s fashion, when compared to the rest of the cast, is racist. 

The wardrobe team did their best to accentuate her Hungarian and African American features, but they did so in a negative way to make a mockery out of her. Whoever was in charge of styling her hair clearly didn’t know how to properly style her naturally curly hair and therefore settled on a halfway version of badly done Utah curls. Or, when Vanessa’s hair was done natural, it was never done correctly, meaning that it would always end up looking frizzy or damaged. 

Compared to the rest of the cast, Vanessa always ended up looking sloppy which is not due to the fact she wasn’t a lead like Blair or Serena, but it was because she was the only person of color in the cast and therefore was discriminated against. The wardrobe team purposely tried to make Vanessa’s character stand out so that viewers would dislike her and idolize Blake Lively and Leighton Meester’s (both of whom are white) characters instead.

 So, when I criticize Vanessa’s fashion, I am not criticizing the character nor the actress. I am directly criticizing the people in charge of making these decisions, as they are the ones who decide what ends up on the screen. 

2. This…“Outfit” Serena wore in Paris

Out of all the things S wore in Gossip Girl, this is undoubtedly my least favorite of them all. The hair alone bothers me because I can’t wrap my head around any reason as to why they would give her a half-braided ponytail that also doubles as a half-braided bun. But that’s not even the worst part about this outfit. The jacket completely throws the whole look off, seeing as the blouse and pants she wears are business casual.

They top the look off with a shimmery gold jacket which makes no sense because she wears this in broad daylight. Even if you took away the jacket, the look still wouldn’t make sense because the pants are cropped short, and our diva S has gorgeous long legs. I know this is Gossip Girl, and they are supposed to be fancy and classy, but this look is just tacky. 

3.  Another One of Serena’s More Than Questionable Looks

If this doesn’t scream 2010 fashion then I don’t know what else does. Taking away the pops of blues in this outfit would have given Serena a more refined look. I think the contrasting colors actually takes AWAY from her look rather than adding her flirty and charismatic personality.

I also dislike how flowy the dress is, as it should fit tighter to give Serena a more regal and elegant look. What would tie this look together is if Serena was stuffed into an outfit that was not her, so her behavior would contrast the complete opposite. Not to mention, the white and black mixed pattern just adds to the distaste I have for this look. It clashes with the blue, and it doesn’t give Serena the fashion credit she deserves. Overall, it’s not my favorite look from S.

4. Trigger Warning: Season 6 Blair Waldorf in a Hideous Outfit Season 1 Blair Would Never Even Touch

I’m not the first and I certainly won’t be the last to say this, but this particular outfit Blair wears in Season 6 does her so dirty. It wouldn’t come as a shock to me if the wardrobe team and Meester had gotten into a fight while deciding B’s outfits for season 6, the grand finale.

I can’t even fathom how they would let Blair Waldorf have such enormous serves in the previous season and then they give her THIS to end it. The clashing of fashion patterns is one thing, but can we just acknowledge for a second if this is a skirt and a top or a dress? Why is the top half of her outfit yellow and green and randomly transitions to white and cream on the bottom? None of this outfit makes sense.

It makes Blair look old in fact, which is wild considering she’s in her early 20s when the series ends. And if you thought I wasn’t going to comment on that little yellow hat they put on her, think again. I cannot even begin to understand why Blair Waldorf would wear a hat (we all know she rocks her headbands), let alone a yellow mini-hat? It just adds to the absurdity of this outfit. I won’t even discuss the lime-colored heels. Too painful. If the goal of the wardrobe team was to make B look like a lemon-lime margarita, then they achieved their goal with this look.

5. Saving the Worst For Last: Vanessa’s Smorgasboard of Very, Very Bad Patterns

I’m not quite sure what’s happening with this outfit, and I don’t think anyone else does either. The clash of patterns of cheetah print, red flannel, gray leggings, and a cropped rainbow jacket feels like whoever dressed Vanessa did so with their eyes closed. Not to mention, Vanessa’s messy ponytail makes her look like she has a weird bump on her head.

I’m trying to find one piece of clothing or accessory that gives this outfit the benefit of the doubt, but I can’t. Even the jewelry Vanessa wears is oddly shaped and like everything else she is wearing, does not match the slightest. This outfit from Vannessa is probably the worst one she wore in the entire show. Even Blair Waldorf’s lemon-like outfit and Serena’s questionable Paris outfit aren’t as bad as this one. Yet again, Vanessa’s outfit is a flop, but are we surprised? She is so heavily villainized in the show and racially profiled by the wardrobe team, so I’d like to say I’m shocked she wore this but I’m not. 

That’s a wrap for the Top Ten BEST and WORST outfits on Gossip Girl. Taking the lead for best of the best are outfits donned by Queen B herself and Serena van der Woodsen, your favorite best friends you love to hate to love. Also SPOTTED on the list are (surprisingly) Jenny Humphrey, Chuck Bass, and Lily van der Woodsen.

As for the worst of the worst, the spotlight shines on V’s trashy looks throughout the show, and S’s more than questionable looks where even her pretty privilege couldn’t get her out of. Plus, B’s HIDEOUS outfit from Season 6 where I wholeheartedly believe someone on the wardrobe team had beef with her. 

Until next time kiddies. In the meantime, you know where to find me. I’ll be exactly where I always am, waiting for you to spill the hottest gossip.

You Know You Love Me

XOXO,

Gossip Girl’s Fabulous Protégé