Wakey, wakey Upper East Siders. The 2000s TV series Gossip Girl gave everything. Voiced/narrated by Kristen Bell, Gossip Girl was dramatic, funny, suspenseful, and extremely binge-worthy. But most of all, the show served looks like no other. The fashion in Gossip Girl was — and still is — unmatched. It became a focal point of the show. Not only were a lot of the main characters’ careers and social lives revolving around fashion-forward spaces, but the producers managed to make each episode feel like a runway event because that was just the energy of Gossip Girl.
From New York City street wear to hot luxury designers, Gossip Girl had it all, and the show’s look book hasn’t been matched in a TV show since. Fashion inspiration from characters like Blair Waldorf (Leighton Meester), Serena van der Woodsen (Blake Lively) and even Jenny Humphrey’s (Taylor Momsen) grunge era was hot in the early 2000s, but is still prevalent today. Even HBO’s reboot of Gossip Girl can’t hold a candle to the original, both in terms of the overall plot and content and, of course, the fashion. Here are the top 10 fashion moments from the original Gossip Girl, ranked.
10 Chuck's Scarves
.webp?q=50&fit=crop&w=1500&dpr=1.5)
Chuck Bass (Ed Westwick) had some of the best looks on his show. His preppy, bad boy fashion choices always had him looking polished and put together, mirroring his personality. Chuck was often seen wearing bold suits, complete with ascots, pocket squares and cufflinks, bringing a sense of wealth and class to the streets of the Upper East Side. However, his most notable accessory were his scarves. A good scarf tied could tie any of his looks together, becoming synonymous with his character. Like his signature J. Press patchwork scarf seen in season one.
9 Chuck and Blair as a Couple
The king and queen of the Upper East Side. Though their relationship had its ups and downs, to say the very least, Chuck and Blair (Leighton Meester) are the ultimate OTP. Both have a stellar wardrobe full of designer and as a couple, their bold, preppy look really stands out among other characters. Like Chuck, Blair is also always dressed to impress, sporting bright colors, flashy prints, designer bags and shoes, and, of course, a matching headband. Every time they're together, Chuck and Blair look Vogue-ready.
8 Serena and Blair's Matching Backless Dresses
Who doesn't love a coordinated look with their bestie? In season one, episode four, Blair and Serena (Blake Lively) steal a bunch of clothing from a photo shoot set after Serena is accused of stealing Blair's spotlight. Following the nasty feedback, B. and S. decided to have their own photo shoot together across NYC. The duo sport matching red and blue backless dresses by Abigail Lorick, paired with slim belts and gold pumps. It's a scene from the show that's extremely memorable, and watching two of the show's lead characters parade around the city in matching outfits makes Blair and Serena's friendship feel so genuine.
7 Serena's Wedding Dress
Of course, Serena van der Woodsen's wedding dress would be elegant and high-fashion. Even better, it featured her signature color throughout the show, gold. During her small nuptials with her on-again-off-again love interest, Dan Humphrey (Penn Badgley), Serena stunts in a glam Georges Chakra gown that completely commands the room. It's as if the gown is made for her and manages to capture her personality and fashion sense throughout the show in one gorgeous garment.
6 Blair's Red Ruffled Gown
In the second episode of the fourth season, Chuck and Blair are at odds, though they're still in love with each other. Chuck is off in Paris, staying with another woman, planning to leave and change his identity, when Serena convinces Blair to intercept him at the train station and convince him to come back to NYC after they learned he was planning to propose before things fell apart. The emotion in the train station scene is so heavy and the delivery is beautiful, just like the stunning red, ruffled Oscar de la Renta gown Blair's wearing. It's one of the most stunning gowns Blair wears in the show and if this were a list of Blair's best fashion specifically, it would certainly be near the very top of the list.
5 Jenny's Grunge Style
Of the entire cast, Jenny's (Taylor Momsen) style was the most dynamic. She starts off as a timid high school freshman looking to simply fit in, so much of her fashion is a replica of what Blair and her group of cronies wear. But later on in the series, she finds herself. Instead of copying the preppy fashion typical of the Upper East Side, she develops an edgy, grunge style, complete with a lot of DIY accessories, as well as her own designs as she starts to pursue her fashion career. While Gossip Girl is well-loved for its high-fashion, New York feel, Jenny's style is unique and a welcomed breath of fresh air.
4 Upper East Side Coat Collection
After the steamy summer, it gets cold in NYC. So the Gossip Girl cast obviously needed a hefty collection of fall/winter apparel. There was no shortage of fashionable cool weather looks on the Upper East Side, but the catalog of coats really takes the cake. From leather jackets to the occasional Burberry trench, everyone's favorite New Yorkers stay warm in style. Truth be told, some of the best and most easily recreated looks from the show come from the various fall/winter styles. Like Jenny's mint trench coat and accenting purple handbag from season one or Blair's bright green winter coat paired with bright, yellow pumps.
3 Blair's Wedding Dress
Gossip Girl saw many a wedding throughout the series' run. And though it was rushed and chaotic, Chuck and Blair's wedding was so romantic and special. It was a long time coming for this unique, on-and-off pairing, so of course Blair's wedding dress had to be just as unique and special as the nuptials itself. For the impromptu Central Park wedding, Blair wore an icy blue, lace gown by Elie Saab. It's a perfect picture of Blair's character, blending both classic glamour and high-fashion. Chuck compliments her gown by wearing a white tux and — just like their streetwear looks as a couple — they go together perfectly. If anyone could ditch the standard white wedding gown and make it fashion, it's Blair Waldorf.
2 Serena's Bridesmaid Dress
Although Lily van der Woodsen (Kelly Rutherford) and Bart Bass (Robert John Burke) as a couple was questionable at best, their wealth and status combined made for a very rich wedding ceremony. Lily's gown was certainly gorgeous, but the real star of the show was Serena. She wore a showstopping yellow tiered, ruffled Ralph Lauren gown with light floral prints. The dress's long, silhouette, keyhole accent and high neckline make this a dress that few people could likely pull off, but of course Serena van der Woodsen is one of them. She paired it with a set of little black gloves, making it the most chic wedding look of the series by far.
1 Blair's School Uniforms
.webp?q=50&fit=crop&w=1500&dpr=1.5)
When people think of Gossip Girl, images of Blair, Serena and other students at Constance eating yogurt and spilling tea on the Met's steps are likely what first comes to mind. B., S. and their groups of followers were known for elevating the school uniform. However, Blair really led the pack on this front. From the bright solid-colored tights, to the designer bags and coats, Blair brought an unmatched sense of pizzazz to her school looks. And of course, you can't forget the signature Blair Waldorf headband. Blair had a headband to match just about any outfit, and the accessory became an identifying part of her character and led to a headband trend off-screen at the time. School uniforms — like most other things — were made cool by Blair Waldorf.