It is no secret that “Gossip Girl” is one of the most iconic TV shows of all time.
The show follows a group of high school students (turned college students) who live in Manhattan’s prestigious Upper East Side, so it’s no surprise that these characters have an abundance of beautiful designer clothes.
Here are 36 of the best looks from the show.
Serena’s Grand Central outfit — Season one, episode one.
The series kicks off with Gossip Girl spotting Serena at Grand Central Station, returning from her boarding school adventures in Connecticut.
This combination of a striped shirt, necktie, and tan leather jacket is a classic one, and set the tone for the preppy yet edgy outfits that the characters would wear throughout the show.
Blair’s white brunch dress — season one, episode two.
Is there anything better than an episode of Gossip Girl where they have brunch? Blair’s white eyelet dress makes her seem innocent but contrasted with her black, lace tights gives the audience an idea that there’s a side of Blair that we haven’t seen yet.
Serena and Blair’s matching backless dresses — season one, episode four.
One of the best scenes of season one had to be the iconic matching photo shoot that Serena and Blair do in their Eleanor Waldorf (really ghost designer Abigail Lorick) dresses in front of the Plaza hotel.
The long-sleeve dresses in red and blue each have a low back and are accented with a slim belt.
Blair’s blazer and red headband —season one, episode seven.
No one really does preppy as well as Queen B though, and this look is one of her best. The red headband sets her apart from her crew of minions and the white crochet tights and yellow-trimmed blazer make for a uniform that even Constance parents likely coveted.
Blair’s sea foam green lace dress — season one, episode seven.
Blair wears this adorable number to dinner with Nate’s parents. Blair later heads to Victrola, Chuck’s new club, for its opening night and, well … you know the rest.
Serena’s gold cotillion dress — season one, episode 10.
Even though Serena may not have been excited to make her society debut, I’d have a hard time imagining that she wasn’t excited to wear this gorgeous gold Pamela Dennis dress. The sleek bodice and voluminous skirt are probably the qualities that her cousin Charlie Rhodes (really Ivy Dickens) liked about it when she steals it in season five.
Blair and Serena’s red and black Constance uniforms — season one, episode 13.
Our favourite thing about Constance school uniforms? They aren’t really uniforms at all. S and B interpret their uniforms in their own way but in this particular episode both outfits feature pops of bright red mixed with black leather.
Jenny’s mint coat and purple bag — season one, episode 14.
Jenny starts to climb the social ladder and her new Upper East Side crowd has clearly rubbed off on her. Her coat and purple bag are definitely status symbols that the girls at Constance respect and not to mention they’re both totally adorable.
Blair’s white party dress — season two, episode one.
This iconic Marc by Marc Jacobs number is worn during one of the most heartbreaking scenes in the series when Blair attempts to tell Chuck how she feels and he won’t admit his feelings for her. But although things didn’t go the way Blair had hoped she still looked absolutely stunning.
Serena’s white party dress — season two, episode two.
Serena may still be a little bummed about the way things ended with Dan but showing up with Nate to the White Party was a great way to heat things up again. The draped dress featured a plunging neckline, which was offset by one of the greatest hairstyles that likely every appeared on television.
Blair and Serena’s Constance uniforms — season two, episode four.
This is another amazing iteration of this school’s uniform policy. Blair rocks a Marc Jacobs cape and a headband and Serena accessories her uniform with a headband and kitten heel shoes.
Jenny’s green dress modelled by Serena — season two, episode five.
When Blair sabotaged her mother’s runway show, Jenny decides to have socialites model the clothes in place of models but Serena ends up strutting down the runway in a dress designed by Little J, not Eleanor. Jenny tells Eleanor to take credit for the short, green showstopper because the fashion show attendees loved it.
Serena’s polo match dress — season three, episode one.
When Serena comes back from her summer abroad, to the surprise of no one her return causes a bit of scene. In an attempt to literally run away from her problems, S mounts a horse at a polo match and rides away with the train of this peachy dress trailing in the background. Name a more fashionable getaway.
Lily’s wedding dress — season three, episode five.
For Lily’s fifth (yes, fifth) wedding she decided to skip the white dress and wear this amazing fuchsia, ruffled gown. It was perfect for a wedding at the Brooklyn Botanical garden and the dangling turquoise earrings made the look.
Serena’s Thanksgiving jumpsuit — season three, episode 11.
A drama-free Thanksgiving? Who wants that? As secrets are revealed and food is served, Serena is also serving us this look. A form-fitting jumpsuit isn’t the obvious choice for a family meal but this one works.
Blair’s glittery dress — season three, episode 17.
I know the plotline of how Blair acquired this amazing gown is a little smarmy but this embellished gown is too good for me to care. The sparkling bodice and the halter neck detail is perfection in dress form.
Jenny’s baby blue lace dress — season three, episode 20.
By the end of season three, no one really liked Jenny that much, but her style is still something that we love. Jenny wore this Marchesa dress to a benefit while she and Chuck conspired against Serena’s father, Dr. van der Woodsen.
Serena’s gold sequin jacket — season four, episode two.
Oh how we wish that Gossip Girl had included a few more episodes set in Paris. Serena’s gold Pucci jacket shines with her cobalt blue trousers and a sleek and intricate ponytail for a look that is trees chic.
Blair’s red ruffled gown — season four, episode two.
My heart stopped beating during this scene just as much for this Oscar de la Renta gown as it did when Blair and Chuck saw each other for the first time since she learned he got shot in Prague. Blair doesn’t often wear red throughout the show, which makes this show-stopping number even more memorable.
Serena’s Fashion Night Out dress — season four, episode three.
This amazing black-and-white printed gown is finished with turquoise beaded detail adding a unique touch to the long dress.
Serena’s red party dress — season four, episode four.
Serena is struggling with her feelings for Dan and Nate and she just can’t seem to choose. My advice: choose neither and marry this burgundy J. Mendel dress instead. The ruched bodice and the cutouts just above the waistline make it feel extra romantic.
Juliet’s tulle ballet dress — season four, episode eight.
Juliet, you were so annoying, but at least you knew what to order from Rent the Runway. In a rather embarrassing scene where she’s wearing this stunning J. Mendel gown, the Upper East Side crew thinks that Juliet is jealous of Serena; they confront her at the ballet. The dress is a good look, but jealousy (or secret evil plans with your imprisoned brother) never is.
Serena’s grey lace ballet dress — season four, episode eight.
Once Juliet disappears, Serena can finally enjoy the ballet on the arm of her former professor Colin Forrester, while wearing this grey dress that features lace detailing and a dramatic train.
Serena’s fuchsia mini dress — season four, episode 19.
Serena’s “cousin” Charlie causes S to be suspicious of Blair hanging out with Dan when she’s supposedly dating Louis. Serena decided to observe B’s behaviour at the Pink Party and does so in this amazing pink dress. The short pink frock features cap sleeves and a mini train of fabric in the back.
Blair’s black floral dress — season four, episode 21.
When Blair finally decides to be with Louis, she still has a hard time letting go of Chuck. After they make an appearance at the Constance Billard alumni fundraiser, she has one final night out with Chuck even crashing a Bar Mitzvah in this stunning dress. The floral accents and sleek black skirt make this a dress that we won’t be forgetting anytime soon.
Diana’s red mini dress — season five, episode two.
The silhouette is simple, but the fit is what takes this dress to the next level.
Blair’s bridal shower dress — season five, episode eight.
Orange isn’t one Queen B’s go-to colours, but we’re so glad she made an exception for this amazing Dior dress. The square neck and the beading make this super lady-like but also keep it young and playful. Not to mention, Blair stood out even more in contrast to the Tiffany blue decorations of her bridal shower.
Serena’s bridal shower dress — season five, episode eight.
And we can’t forget about the bridal shower hostess, Serena. She looked radiant in this angelic Mary Katrantzou mini dress and in a nod to the shower theme of Breakfast at Tiffany’s she has layered some pearls over the outfit replacing her often more edgy jewellery.
Serena’s gold dress — season five, episode nine.
Serena and Charlie try to keep the peace between their mums for a party at Studio 54 that is being thrown in honour of their grandmother, CeCe. They never make it to the party of course, which is a shame because someone other than Serena’s fake cousin and her fake cousin’s ex-boyfriend deserved to see her in this stunning, gold Diane von Furstenberg dress.
Ivy Dickens gold dress — season five, episode 10.
This mid-season finale left us on quite a cliffhanger, and even though Charlie/Ivy was responsible for many of the problems in this episode, her gold Badgley Mischka dress was nothing but perfect.
Blair’s casino dress — season five, episode 24.
When Blair finds Chuck in Monte Carlo wearing this beaded dress, she delivered one of the best lines in the series: “You always said I bet against you, but this time I’m all in.” She shoved all of her chips into the center of the table.
Blair’s fashion show dress — season six, episode three.
Now that she’s taken over as head of her mother’s company Waldorf Designs, Queen B has a lot riding on her reputation, including making sure her debut runway show goes well. As we all know that didn’t go as planned, but before the chaos ensued at least Blair got to wear this Valentino dress and enjoy a moment of calm.
Georgina’s black sequin dress — season six, episode five.
It wouldn’t be a season of “Gossip Girl” without some good old Georgina Sparks meddling. G wears a long, black dress with gorgeous silver beading at the neckline as she crashes yet another “Gossip Girl” debutant ball. The dress, like her takedown plan, is a perfect 10.
Blair’s wedding dress — season six, episode 10.
Since Blair already did the princess wedding once, she keeps her second wedding dress true to her own personal style. This amazing Elie Saab number is a sparky powder blue gown and Chuck wears a white tux with matching blue accents for their whirlwind wedding in Central Park. Right before the cops take them away.
Serena’s wedding dress — season six, episode 10.
At the end of the show, there is a five-year time jump where we see everyone in Blair and Chuck’s townhouse getting ready for an event. The event is of course, a wedding, and Serena and Dan are finally tying the knot.
Serena’s stunning white and gold dress is courtesy of Georges Chakra and makes her look like she floats down the stairs where she says her vows to her high school sweetheart.
Lily’s wedding guest dress — season six, episode 10.
And let’s not forget about Lily’s lavender dress. The dress features a mock neck and beaded detailing giving her a fashion-forward look that is much more street style than mother of the bride.
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