Top 10 Serena & Blair Fashion Moments

Serena’s fashion stayed relatively consistent throughout the series, leaning boho chic with a more seductive edge. She was right on point with the gown she wore for her mother’s wedding to Bart Bass in the first season of the show. The dress was designed by Ralph Lauren for his collection in the spring of 2008 and it comes as no surprise that the show’s costume designers snagged it for filming. The bright yellow hue compliments Serena’s golden locks, and the ruffles and keyhole neckline add an extra element of visual interest.

The fashion on “Gossip Girl” is always at the top of its game, but the producers arguably never outdid themselves as much as when Serena and Blair spent their summer vacation in Paris. Of course, the looks they chose there would have more of a European flair than the tried and true Upper East Side outfits we were used to seeing the girls wearing. In the show’s opening scenes, Blair wore a multi-print dress by Italian designer Moschino with a blue beret because of course she did. Serena’s outfits throughout their stay in the City of Lights were also gorgeous, if somewhat out of character. But hey, when in Paris!

When Constance Billard and St. Jude’s decide to put on a senior production of Edith Wharton’s “The Age of Innocence”, which is set in high society New York in the 19th century, you know the fashios choices are going to be good. Both Blair and Serena turn it out in gorgeous historically themed gowns that have been modernized just enough to not look out of place in the 21st century. Blair’s is black, high necked and severe while Serena’s is light, floaty and feathered - perfectly in keeping with each girl’s respective fashion sense and personalities.

The creators of “Gossip Girl” took any chance they could to dress their characters up in fabulous outfits, so organizing a masquerade ball was a natural choice. Blair’s dress choice isn’t dissimilar from the one she wears later for her “Age of Innocence” performance - black, lacy, and all covered up. She of course pairs it with opera length gloves. It’s the yellow dresses that are the focus of the evening however, with both Jenny and Serena sporting similar bright colored gowns that ends up causing some inevitable mix ups.

One of the most shocking moments of “Gossip Girl”’s first season came when Blair let go of all her tight laced inhibitions and performed a strip tease at Chuck’s burlesque club on a dare. While she may start the night in her typically prissy headband and pearls, once she sheds her outer layers she’s in perfectly Blair-appropriate under things that manage to be alluring while still not venturing into the realm of truly outrageous. This marks the beginning of the Blair and Chuck saga and, given the outfit and her performance, we can understand why they both left club feeling hot and bothered.

Audiences knew that the show’s costume designers were going to have a field day when it came time to dress the cast for prom and they definitely did not disappoint. Blair’s stunning Marchesa gown from the Spring 2008 collection is practically emblematic of her character, with the dark baroque style and intricate pattern giving fans exactly what they expected from their favorite Constance A-lister. Serena on the other hand wore something similarly character-appropriate. Her sparkly dress was fun and irreverent, which is what we had come to expect from Miss Van Der Woodsen.

We already talked about how globally gorgeous the girls’ looks were on their trip to Paris, but there’s one outfit that we’d be remiss to not put the spotlight on. When Blair has an encounter with Chuck the Gare du Nord train station, she wears a dress so beautiful that you forget to question why she happens to be wearing such a dramatic ballgown. The gown is Oscar de la Renta and its crimson hue likely represents the emotional turmoil Blair is experiencing in this scene. Symbolism aside, we’d kill to get the chance to wear something like this.

When Blair was set to wed Prince Louis Grimaldi of Monaco, the gown she chose was unsurprising and somewhat unremarkable. The ivory Vera Wang ballgown may have been pretty, but it didn’t have a whole lot of personality. In the series finale however when we finally get to see Blair and Chuck say their “I Do’s” near the Bethesda Fountain in Central Park, she wears something blue instead of something typically bridal. The intricately embellished Elie Saab is a real statement piece and represents this fashionista much more than the cookie cutter dress she wore in the earlier season.

While it seems that Constance Billard became increasingly lax with enforcing its school uniform as the seasons wore on, at the beginning, the preppy style was prevalent on the show. In the earliest episodes of “Gossip Girl”, we got to see the girls’ individual takes on uniform dressing, with Serena taking a casual untucked approach and Blair amping up the prep with knee high socks and her signature hair accessory. Before Jenny takes her edgy turn, she appears wearing a pinafore style take on the mandatory plaid skirt, which shows just how innocent she is. As these three prove, an outfit is worth a thousand words.

Before we unveil our top pick, here are a few honorable mentions.

Serena's Bridesmaid Dress

Indecent Proposal

Serena's High Low Dress

Is there any more quintessential fashion item from the “Gossip Girl” age than this? Blair’s headbands, which played a larger role in earlier seasons but still appeared throughout the rest of the show, were a marker of the character’s sartorial personality. The character started a trend with accessories flooding Forever 21 stores worldwide to be accessible even to those who didn’t reside on the Upper East Side. Similarly, her brightly hued tights added a pop of color to otherwise neutral school uniforms and made her stand out from the pack as someone to be reckoned with.