Most Iconic Fits From Gossip Girl

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Attention Upper East Siders, do the names Blair and Serena ring a bell? Well here are the Most Iconic Fits From Gossip Girl seen throughout the entire show!

From around 7th grade to now, the CW’s hit Gossip Girl has always been one of my all time favorite shows. Between the incredible cast, crazy story lines, and exquisite fashion, this NYC based show is truly a staple of our generation. Despite their being the new reboot, the OG Gossip Girl cast will always have a special place in my heart. Gossip Girl has been known to have some of the most glamorous and unique fashions seen on a teen drama that will forever remain iconic. Blair practically reinvented headbands, Serena carried the best designer bags while rocking an effortless blowout, little Jenny Humphrey did the classic switch up from her innocent girl vibe to the gothic, yet glam look and don’t forget Chuck’s questionable scarves in season 1.

The show has featured numerous pieces from top fashion designers around the world such as Tory Burch, Vera Wang, Marc Jacobs, Prada and more. Any fashion lover can appreciate the insane costume design skills used to create the picture perfect fits that kept the audience wanting more and more. Check out some of these most iconic fits from Gossip Girl, (even though really all of Blair Waldorf’s Fits are impeccable). If you have yet to watch this award winning show, watch out for some spoilers!

1. Blair’s White Party Dress

In the first episode of Season 2, Blair is seen wearing this iconic look at the White Party in The Hamptons. This Marc Jacob’s summertime dress was quickly a fan favorite after the episode first aired. Blair looked effortless, pairing the mini dress with her traditional headband, pearl jewelry, and a white clutch.

2. Serena’s Wedding Dress

Serena wears this stunning strapless ball gown in the final episode of season six. She’s spotted in this golden piece by designer Georges Chakra couture. Serena has many iconic fits from Gossip Girl, so no wonder she would pick out such a wild, yet beautiful wedding dress to rock as she marries Dan Humphrey. Not to mention her side swept updo paired with gold jewelry adds to the look even more!

3. Serena And Blair’s Photoshoot

In Season 1, episode 4 Serena and Blair have a photoshoot for Elenor Waldorf Designs. In this shoot taking place in the NYC infamous setting of Central Park, Serena and Blair wore matching red and blue dresses. The backless, high neck design paired with thin belts hugging the waist make for a simple, yet elegant design you could still wear today. The girls paired the knee length dresses with matching gold metallic heels to complete the fit.

4. Vanessa’s Silver Gown

As a true Gossip Girl stan, I can confidently say Vanessa is one of the top characters that gets on my nerves the most, but I couldn’t help but include her fabulous silver gown worn at the snowflake ball on this list of iconic Gossip Girl fits. The silver shimmery Eric Daman Dress features a one shoulder design paired with an oversized shall on top. This dress seen on season 2 is defiantly something different for Vanessa’s general style (so maybe that’s why I like it?) Her hair, makeup, and accessories pair perfectly with the gown, making this one of Vanessa’s best fashion choices throughout the show.

5. Blair’s Summertime Flare Dress

In S2:E1 Summer, Kind of Wonderful, Blair wears this summery white flare dress with vibrant floral prints. This dress fits Blair’s summer aesthetic perfectly, pairing the dress with a chunky, bright pink belt and Kate Spade bag. What would a class Blair outfit be without adding her signature headband (but of course not one we’ve seen already!). This whimsical and playful look is one of my all time favorite iconic fits from Gossip Girl that Blair truly radiates in.

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6. Blair’s Red Strapless Gown

I think most Gossip Girl fans can agree that one couple we love too much is Chuck and Blair, despite their toxic history. In the episode “Double Identity,” Blair meets up with Chuck at the train station in Paris. She blows Chuck away as she enters wearing this Oscar de la Renta gown that proves red is HER color. The strapless designer gown adds a lot of texture, covered head to toe with ruffles. But leaves room to see her heels with a higher cut in the front. The gown makes this well known moment in the show even more memorable and iconic. Blair’s look is paired with bold makeup and a burgundy clutch.

7. Serena’s Sultry Black And Silver Sequin Dress

Flash forward to the final season of the show, Serena is seen wearing this Peter Pilotto Fall 2012 Collection Dress in the episode “Save The Last Chance.” This form fitting dress features a high neck line with unique cut outs. The dress is black with silver sequin detailing and sheer fabric by the waist. Serena pairs the look with a high, slicked-back pony, natural makeup, Valentino clutch and no jewelry, allowing the dress to make a statement on its own. This dress could totally still be worn today at any formal event, making it one of the most timeless, yet iconic fits from Gossip Girl.

8. Jenny Humphrey’s Little Black Dress

No character’s personal style changes more throughout the show than the infamous Little J herself. Jenny Humphrey started off the show simple being known as Dan Humphrey’s innocent younger sister. Jenny becomes instantly fascinated with the lives of the Upper East Siders and has a drastic style change that will remain throughout the series. Actress Taylor Momsen who played Jenny was starting a rock band at the time and completely changed her look, so the writers decided to change Jenny’s style as well. Her style was seen as more goth, wearing generally only dark clothing. She also could be seen with long, bleach blonde extensions and dark, heavy makeup. One of my favorite looks after her style change is this one shoulder, little black dress featured a sequin design.

Let us know which one of these iconic Gossip Girl Fits is your favorite! Xoxo, Gossip Girl.

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