Gossip Girl is one of the most exciting television shows. It is full of thrills and drama, and since it focuses on affluent and attractive characters on the Upper East Side of New York City, there's a lot to see in terms of style. And with all that class came an array of fabulous outfits!
These characters were always attending functions and galas, were always heading out on shopping sprees and lavish vacations, and were always hosting luxurious parties and social gatherings. That being said, fans sometimes just tuned in to see all the fashion choices.
After all, these characters had endless resources on hand to craft the most amazing outfits, thanks to an ever-revolving closet door! The show may have ended years ago, but that doesn't mean fans have stopped memorializing the most iconic fashion moves from Gossip Girl, and it definitely doesn't mean fans have forgotten about their favorite NYC socialites. Then again, Blake Lively isn't one to shy away from fashion off the set, either.
From casual outfits worn by Serena van der Woodsen and Jenny Humphrey to fancy garments seen on Blair Waldorf and Chuck Bass, these are the 20 most fashionable moments from Gossip Girl.
20 Serena’s & Blair’s Dresses
Since Blair’s mother was a fashion designer, some of the stylish moments came about due to her clothing line. At one point, Blair could have even been the face of her mom’s line, but—of course—Serena stole the spotlight away.
In the end, though, the two friends ditched the photoshoot, stole some clothes, and went off to have their own shoot.
And the result of it all gave us these iconic poses in these iconic dresses, which made us wish we could have a day like this with our BFFs (or just with Blair and Serena, maybe, too!).
19 Serena’s Coat + Boots
New York can get super cold, so there was some great winter wear seen over the course of this series—like this coat and these boots. Here, Serena is just walking down the street and having a phone conversation, but she looks amazing. This gray coat is a great staple piece. Those tall boots almost make us wish winter would stick around, so we could wear something like this (almost). Plus, the printed tights, neutral handbag, and matching gloves are nice accessories, which help tie together the entire ensemble. No one does winter chic like this It Girl!
18 Blair’s Brown Cape
Oh, this fall look is too adorable, and it is perfect for a girl like Blair; she has a birthday in the fall (November 15), and her favorite holiday is Thanksgiving (mmm those pies), so it makes sense that her style would shine even more than usual during this time of the year.
Usually, her clothing items were a bit preppy, but sometimes, she went for a sweetheart look.
The ruffles, the layers, the lace and the frills of this look are quite romantic. And then, like a cherry on top, we have this little brown cape, which is the most darling thing ever.
17 Chuck’s Burgundy Blazer
The ladies of the show were not the only ones who stood out, though. Chuck Bass was a lot of things, and fans grew to love him and his relationship with Blair and how much he grew up. Oh, and we always enjoyed seeing what he would be wearing, too! Many of his garments were also preppy, and they were all luxurious (only the best for a Bass!), such as this burgundy blazer. The velvet material, the coordinating accessories, the gray layers, the matching socks... This is a good one of his, indeed.
16 Jenny’s Winter Outfit
Jenny Humphrey also had some big fashion moments on Gossip Girl. Early on, she was sweet and innocent in her little school uniform, but as the show progressed and as she did, we saw some really dramatic, dark, and edgy pieces.
This winter outfit, for instance, has patterned tights (a staple within this world, apparently), a great pair of combat-style boots and an over-sized coat.
Little J loved wearing volume on top and showing off her long, thin legs, which she did so well. Plus, of course, the fashion designer in her accessorized with all the right details, too.
15 Serena’s Pops Of Color
One of Serena’s best moments is pictured here. It does not matter what was underneath this coat, where she was going or what season this was. All that matters is that a. This coat exists and b. It is not the only pop of color! Yes, this outerwear piece is the perfect blend of fun and functional. Plus, it has pockets, too, which is an added bonus. Then, to really finish off this look, Ms. van der Woodsen added this big and bright blue clutch—another fun and functional piece. We love it.
14 Blair’s Skating Outfit
Here is another sweet and romantic look from Blair! When ice skating with her family, she was seen in this brown plaid outfit, with drapes and cuts in all the right places.
Underneath, she wore pale pink, and to stay warm, she added white tights, long white gloves, and the cutest white pom-pom hat.
So, she is staying true to herself (with plaid and tights—staples in this Queen B’s closet), but she is, once again, bringing even more than usual with this lovely winter outfit that always stands out to us!
13 Young Lily & Carol
Of course, we have to talk about Young Lily van der Woodsen and her sister, Young Carol Rhodes. A memorable episode of Gossip Girl traveled back in time to show these siblings at a younger age. While that alone was a fun experience for fans, it was made even better with these awesome pieces from the ‘80s! On the left, we see Lily with exaggerated shoulders, bright colors, and a mix of patterns and materials. On the left, we have Carol in a headband, a denim jacket, and amazing white leather booties. These girls just wanted to have fun!
12 Nate & Vanessa's Fancy Look
Next up are two characters who have not been mentioned yet but who knew how to clean up nicely: Nate Archibald and Vanessa Abrams. Now, opinions may differ when it comes to whether or not these two should have ever been together, but let’s at least give them this moment!
Nate enjoyed video games and sports, but Nate in a suit... Yes, please!
And Vanessa definitely brought the hippie vibe to the Upper East Side, and during this particular scene, she was still showing off her unique style, while still looking glamorous and elegant.
11 Serena’s Glamorous Dress
For some, they picture this dress when they think of the fashion of Gossip Girl, which makes sense. It kind of summed up Serena van der Woodsen herself. It was glamorous (and probably definitely expensive). It was long and slim (just like this pretty female character). It was a show-stopper (with the beading and the draping). And it had just enough allure (to turn even more heads in her direction... not that she needed any help with that). Yes, Serena always looked fab, but this dress may have been her best moment of all time.
10 Chuck’s Colored Bowtie
Chuck definitely enjoyed dark pieces, which sort of went along well with his dark and brooding presence and tough guy mood, but fans realized he was a sweetheart, a lover and real, caring human being.
So over the course of the show, pieces like this were seen on this character, too—light and happy pieces (which were still super luxurious).
This springtime look consisted of a tan-colored suit, a pink-and-white gingham shirt, a green patterned bow tie, and a nice little pink flower on his lapel. While Chuck Bass in a dark suit is everything, this bow tie look is so wonderful!
9 Serena’s Gold Blazer
Serena loved to stand out in the crowd, and one way she did that was with eye-catching materials. The main object here was this metallic gold blazer. It would be great thrown over a dress or paired with jeans, but this girl took it up a notch. Yes, Serena’s other object of desire here was a pair of electric blue pants. And it was the perfect combo: She looked youthful and vibrant but also professional and put together, too, which caused many fans to want to copy this look back in the day (and maybe still today).
8 Blair’s Purple Look
Now, this next look may not stand out in everyone’s minds as much as some of the other outfits on this list, but this is a fave for sure. When Chuck showed Blair the hotel he was going to buy, Blair was wearing this. And each piece here, on its own, was so perfect, but together... She looked amazing.
The top was a flirty and frilly little purple blouse, perfect for a sunny day.
The printed pencil skirt was professional yet youthful. The pink clutch added another flair, with its unique handle. She just looked as fresh and as bright as the day was around her—too pretty!
7 Jenny’s Accessorized Dress
Here is Jenny in more edgy, oversized clothes! This time, though, her main garment was a short and tight dress. She added shoes that were chunky and studded. She carried a purse that featured studs, too. Layers of chains were worn around her neck. A braid could be seen hidden in her hair. And top of it all, she threw on a black cardigan with thumb holes. Jenny certainly had her style down, and love it or not... This was a big and memorable moment when it came to fashion on the show Gossip Girl.
6 Serena’s Gold Dress
Oh, look—more metallic gold! This dress is another fan favorite, for the series overall and for Serena especially. And we don’t know about anyone else who is reading this, but... No one ever looked like this at our school dances!
But then again, we did not grow up on the Upper East Side. We did not have closets as big as a van der Woodsen’s.
And we are not Serena, this It Girl like no other. Only she could have pulled off this look, gotten away with a dress like that and looked this stunning in this gown fit for a princess.
5 Blair’s Red Dress
On a similar note, fans fell in love with Blair in this dress. On its own, it is a stunning piece, with that red color and those big ruffles. On our Queen B, though, it became something more, and we are probably all picturing this scene now when Blair and Chuck reunited. We can hear Eva Coupeau (Chuck’s girlfriend at the time) asking who this beautiful woman was, knowing that she was special—in general, and, especially, to Chuck. Yes, when it comes to Ms. Waldorf’s shining moments, this was a stand-out time.
4 Chuck’s & Lily’s Coats
Remember that if we have learned one thing, it is that coats were a big deal on this TV show! Therefore, here are two more great ones. They were both neutral in color, meaning they could be worn with many, many items.
They both had nice little details, such as the patches and buttons on Chuck’s and the collar and cuffs on Lily’s.
And while some may think that a functional winter coat, specifically a tan one, could come across as boring, these two stylish characters set the standards for us all!
3 Georgina’s Statement Hat
We had to: We may not forgive Georgina Sparks for all she did on this series, but we had to include this moment. She found out about the wedding of all weddings (well, at the time), as Blair and Prince Louis can be seen on the newspaper in her hands. And when she read the news, she was wearing this: printed tights (of course), a detailed black coat (with silver buttons and a pattern across the shoulders), and *the* hat. Say what must be said about this character, but that hat made a true statement and belongs on this list!
2 Dan & Serena’s Wedding Ensembles
Okay, the end is near, but so it is time to all reminisce on one of the biggest moments of Gossip Girl. In the series finale, as we know, Gossip Girl was revealed, time jumped forward, and Dan and Serena tied the knot.
They did so surrounded by only their closest friends and family members, and they did so looking like this.
Dan has not been mentioned here today yet, but look at him—how truly dapper! And Serena, well... To say she looked gorgeous in this wedding dress would be a true understatement.
1 Blair’s Wedding Dress
To end, we are including our personal favorite piece from all of Gossip Girl—Blair’s blue wedding dress, her true wedding dress, her real wedding dress, and her final wedding dress! Her wedding with Chuck was one of the most memorable scenes from this series, as their loved ones came together to make the quickest ceremony ever happen. Though it was quick, the bride still had to look stunning, and she did! She also looked like a true princess in this detailed piece and that embellished headband. Seeing her fairy tale play out and lead to this moment and this dress was everything.