5 Best Fashion Moments On "Gossip Girl"

Take me back to the Upper East Side

When Gossip Girl premiered back in 2007, many of us were just awkward, scrawny teenagers on the brink of adulthood. So watching these fictional uber-rich teenage socialites live their scandalous lives was the ultimate guilty pleasure and wish fulfillment for us. It's not only their interesting (albeit completely unrealistic) lives that we were slightly jealous of, but also their astonishing wardrobe and beauty arsenals.


From Blair Waldorf's preppy style to Serena Van Der Woodsen's boho chic, we were completely stunned by how unbelievably fashionable New York's Upper East Side teens are. In celebration of Gossip Girls' 10th anniversary, we're rounding up the show's five best fashion moments in all of its six seasons. You know you love it, XOXO.

Blair And Serena Wear Eleanor Waldorf Designs

Remember that episode back in season 1 when Blair and Serena got into a fight because Blair's mom chose Serena to model for her brand instead of her own daughter? If you do, then you'd also know that they eventually made up, decided to ditch the whole thing and instead had their own photo shoot around New York. 

It's the first scene since the pilot where we saw the genuine friendship of these two leads. We're loving the twinning outfits featured in the episode, particularly these classy, backless dresses paired with matching golden pumps. Yay for friendship and fashion!

Serena's Ralph Lauren Bridesmaid Dress

This Ralph Lauren Ruffled Fillipa Dress perfectly encapsulates Serena's reputation as New York's It Girl or "Sunshine Barbie" as Blair puts it. She looks perfectly gorgeous and radiant in this dandelion, floral print. We're also loving the unique take on the halter cut which featured ruffles to match the dress.

Jenny Humphrey's Street Style

Jenny started out as "Little J," a young social climber who idolizes Blair and her gang. Throughout the seasons, we saw her crawl out of Blair's shadow, ultimately becoming Constance's new queen bee. Despite ending up as hard-core Queen J, we'll always have a soft spot for her on-point street style. Here we see her mix and match layers of clothing. A nice outfit inspo for when we're travelling to countries with colder climates.

Blair And Sarena's Matching College Outfits

Few high school TV dramas make it into college and Gossip Girl is one of them. Although the plotlines are not as deliciously gossipy compared to earlier seasons, the show's fashion game remained strong. Just check out Blair and Serena's complementary outfits during their stay at Columbia University.

We're especially drawn to Blair's yellow-orange printed dress from Nanette Lepore. The interesting patterns worked so surprisingly well.

Blair's Blue Wedding Dress

Who knew that Chuck and Blair's once toxic relationship would turn into a loving one? We did, and you did! So we were all very happy when they finally tied the knot in a simple ceremony at Central Park. To match the intimate vibe of the wedding, Blair wore a simple, straight-cut baby blue wedding dress designed by Elie Saab. 

(Cover photo from: TheCW@gossipgirlstyles)

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