10 Gossip Girl Looks We Love!

Beauty & Style

Hey Upper East Siders, Gossip Girl's fifteenth anniversary is coming up on September 19th! Throughout the years, the iconic television series impacted twenty-first-century fashion around the world.

The designers of the show took extra care to make sure each outfit was perfect. Former Gossip Girl costume designer Eric Daman told Fashionista, “Blair never repeated a headband in six seasons, and Serena never wore the same pair of shoes or carried the same bag.” Whether it was Blair’s signature headbands or Serena’s chic ensembles, Gossip Girl made sure each character had a unique signature style that reflected their personality and story.

What really stood out about the closets of the Manhattan teens was how they did not often conform with the fashion trends of the 2010s. While some looks might seem outdated and easily forgettable (sorry Vanessa), others were simply show-stopping. Today we are going to be counting down our top 10 Gossip Girl looks of all time!

1. Serena and Blair’s Matching Dresses

We are living for this matching look! The matching ensemble looked put together, but carefree enough to roam the streets of New York. B and S were spotted wearing backless open sheath dresses stolen from Eleanor Waldorf Designs. However, the bold, opposite colors are what made these outfits really shine. Each girl also sported metallic high heels and a string belt of the opposite color. This entire scene was chef's kiss.

2. Blair’s Ellie Saab Wedding Gown

Blair’s wedding dress to Chuck Bass seemed perfect for the occasion! There was something very special about Blair opting out of the classic white ball gown. This felt like an unconventional but classy dress for an unconventional, unpredictable relationship. It showed she had matured from the high school prom queen we knew in Season 1 into a mature young lady who was no longer obsessed with living a fairytale-like life!

3. Serena’s Green Dress

Even though 95% of the population would look like Tinker Bell in this mini-dress, Serena Van Der Woodsen looked unique and beautiful. The drama surrounding this dress made it even more memorable! Blair tries to ruin her mother’s fashion show, so Jenny tries to salvage the show by having socialites walk the runway instead of models. However, Serena accidentally ends up wearing a dress that Little J designed. Of course, the entire crowd ended up loving this eccentric-looking dress.

4. Blair’s Red Ruffled Gown

Blair looked absolutely stunning in a bright red, ruffled Oscar de la Renta gown. She also wore a matching necklace gifted to her by Prince Louis and pink pumps. The entire outfit makes her look like a true American princess! Not to mention that this is the iconic train scene where she sees Chuck for the first time since she found out he had been shot.

5. Lilly's Wedding Dress

At Lilly’s FIFTH wedding she decided to opt for something more low-key. Maybe she was feeling burnt out by her last four obsessive and manipulating husbands? For her wedding with Rufus, she chose a fuchsia dress with ruffles at the neckline and turquoise raindrop earrings. The colors felt perfect for her modest botanical garden wedding. Overall, the dress felt like a perfect way to begin a more family-oriented, down-to-earth chapter in her life.

6. Max's Yellow and Blue Striped Suit

One of my favorite things about the styling choices in Gossip Girl is how they focused on the male outfits too. Many shows overlook the outfit choices for male characters because they believe that people notice them less. However, Gossip Girl has managed to give each male character a distinctive style that matches their story and personality. This suit has eye-catching colors and distinctive patterns that help make the outfit look sleek and sophisticated! This bold and daring outfit is perfect for Max, who isn’t afraid to try new things or stand out from the crowd!

7. Zoya Lott's School Uniform

I am living for Zoya Lott’s laid-back, schoolgirl vibe! Her outfits seem normal and realistic for a girl her age — something which many high school shows struggle with! In the original show, characters often expressed themselves through their school uniform. Zoya, however, decided to make her uniform look more casual — which might be a nod to how she does not feel the need to fit in. Perhaps, her style will evolve into something more sophisticated like Jenny Humpry’s as she becomes more knowledgeable about the Upper East Side. Either way, we are digging this oversized sweatshirt that is paired with a matching plaid skirt (in the Constance Billiards official colors of course).

8. Serena's Grey Lace Gown

This dress screams it-girl! It shows off cleavage and skin in an elegant and sophisticated way that would be appropriate for a ball or New York event! I am in love with all the beaded details and the lace sleeves. After all, who could forget this jaw-dropping Zuhair Murad gown?

9. Jenny's Goth-Style Uniform

Speaking of Little J’s style evolution … she is rocking this rebellious, e-girl look! Jenny is dressed in a way that completely stands out from the other girls at Constance. This seems like a complete character arch, considering how in season one all she wanted to do was to look like Blair’s minion! In this episode, she decided to wear a basic black top and jacket and pair it with pops of color, such as her red purse and metallic boots. This look was actually inspired by Taylor Momsen’s personal style evolution! As Queen B herself says — “she is the gothic barbie of NYC!”

10. Blair's Prom Dress

This might be the most meaningful and romantic outfit worn on Gossip Girl! Chuck, who is secretly in love with Blair, decides that he wants to make sure Blair has the magical prom night she has dreamed of since she was a little girl! This includes making sure she is the prom queen, buying her dream dress, reserving the penthouse at the Plaza, and sabotaging her corset because he thought she looked better without it. He anonymously sends her this black Marchesca ball gown that is perfect for a prom queen! The costume designer for Gossip Girl told E-Online “A Simon Tu tiara tops it off with gleaming crystal rosettes. Simon is one of NYC's best-kept secrets; his beautiful boutique is a gem and only a stone's throw from Bloomingdale's.” This strapless black ball gown with a gold peacock design will definitely go down as one of the best looks in Gossip Girl history!

Which outfit was your favorite? Who do you think has the best style of gossip girl?

Diya Mehta

Diya Mehta is a freshman at University of Toronto Schools and an aspiring writer. She is currently a writer for The Teen Magazine and a columnist for The Incandescent Review. She is passionate about writing, reading, mental health advocacy and history and has national awards from Access To Justice, Technovation and Moonshot TKS. When she is not writing she enjoys playing the piano, skiing, baking cupcakes and binge-watching Suits.