Ah…Gossip Girl. One of the most iconic television shows of the 21stcentury. Though it was provocative, controversial and older generations didn’t seem to understand it, GG shaped an entire generation of predominantly 90s girls. Revolving around the lavish and drama-filled lives of Manhattan’s uber-rich kids, Gossip Girl touched on every topic teenagers could relate to - minus the billion-dollar trust funds. It was thrilling, half to do with the fact that us viewers were so envious, yet so enticed by the character’s lives – regardless of how twisted they were. Though the show consistently kept us at the edge of our seats awaiting the next week’s episode, the most alluring part of the show was the fashion.
We were truly blessed with Eric Daman, costumer designer for Gossip Girl as well as Sex and the City. He carefully curated each character’s individual style to express their personalities - and to say he hit the nail on the head would be an understatement. Most of the characters were dressed only in luxury fashion and carried only the highest-of-the-high-end designer handbags. The show debuted in 2007, so oversized Chanel totes, XL Fendi Peekaboos and large, colourful Dior bags were basically the only suitable accessories to be worn by the elite characters.
Bad girl gone good, Serena van der Woodsen was the principal character. She was the stereotypical definition of a rich, city-living It-girl; strikingly beautiful, misunderstood and troubled. Though she had a heart of gold (when she wasn’t effing over her best friend Blair), Serena’s carefree attitude made her reject the norms of her extremely privileged Upper East Side upbringing.
There would be no doubt that Serena would be the face of Chloé if GG was set in 2019. Her long, flowy blonde hair, love for peasant skirts and free-spirited personality would make her the ideal Chloé girl. Though her bag collection mostly featured colourful handbags that would make us cringe today, her overall boho style would make her a modern fashion icon. She’s chic, but practical and laid back. Her effortless, nonchalant lifestyle means she would undoubtedly carry a Chloé Faye. She’s often jet-setting around the world to escape her seemingly never-ending problems, so she needs the medium size that can easily balance fashion and function. Chloé is also a brand that’s acclaimed for its understated glamour. Though Serena’s mother may have deposited six figures into her bank account, she was never the flashy type. The Faye is discreet enough for her and doesn’t scream “designer,” making it the obvious choice of arm candy for Miss van der Woodsen.
Blair Waldorf was the “villain” (even though that’s up for debate) who always had her life together. The Queen Bee of Constance Billard private school, though Blair may have been popular, she seemed to always live in Serena's shadow. The ultimate bad b*tch, Blair was determined, ambitious and wouldn't let anything (or anyone) get in the way of her dreams. When she’s not scheming against people, achieving the highest grades in her class, or bailing Serena out of trouble, she’s seen on the steps of the Met museum eating yogurt with her “minions.”
Prim and proper, her style was conservative but incorporated playful, youthful elements as well. She was more or less the definition of “teenage femininity.” Though Blair resided in Manhattan, she would often visit her father in Paris. Boatnecks, berets, skirts and a whole lot of colour dominated Blair’s wardrobe. As for her accessories; headbands, Chanel pearls and Lady Dior’s were necessary additions to all of her outfits. If Blair Waldorf was around in 2019, the bag that would be on her arm at all times would be the Gucci Sylvie. A classic design with traditional features, Blair is a young perfectionist with a go-getter attitude which means she needs something mature but also something suitable for her age. The Gucci Sylvie is the perfect mix between traditional and contemporary, plus it’s super girly and fun. Though we think the black version would suit her best, there’s no doubt that Miss Waldorf would have the Sylvie in every single colour.
Jenny Humphrey, better known as Little J in the first season, was the opposite of Serena due to the fact that she was a good girl gone bad, gone good, gone bad, gone good again. Jenny was basically all over the place. Growing up “poor” (even though she lived in a stunning, exposed brick, open-concept loft in Brooklyn and attended the same private school as the Upper-East-Siders) Little J was a sweet girl who idolized the luxurious Manhattan lifestyle. With dreams of being a fashion designer, Jenny went from being the cutest little blonde girl you could imagine to a full-blown punk rock chick with bad intentions.
If it were 2019, first season Jenny would have definitely invested in a second-hand, vintage monogram Mini Saddle bag from Dior – and it definitely would have been pink. The Mini Saddle was discontinued in the early 2000s and only the larger version was revamped on the runways in 2018. Jenny would’ve have been able to afford the hottest pieces right off the runway, so she’d have to settle for something from the consignment store.
Desperate to fit in with the It-Girls, Little J would do anything to keep up with her frenemies expensive lifestyles. Saving her pennies to afford a small, somewhat inexpensive Dior bag just for appearances is typical Little J behaviour. Impressionable, vulnerable and determined to be a “Canal Street Blair”, a vintage monogram Saddle would fit right in with Jenny’s girly, colourful and youthful style filled with frilly skirts, pink nylons and second-hand pumps.
By the end of season 2, things started to change for Jenny. Her style went from girl-next-door to girl-off-the-rails. Fishnets, combat boots, leather jackets and impossibly short skirts were the only things inside Jenny’s closet. Let’s not forget how she also dyed her hair platinum blonde and didn’t leave the house without raccoon-like makeup. Little J was dead, and the new Jenny would need to carry an edgy bag that matched with her grungy, rock n’ roll aesthetic. Not to mention, by season 3 she had moved on up from Brooklyn to a UES penthouse due to the fact that her father married Serena’s mother. In 2019, Jenny wouldn’t be caught dead with the pink Mini Saddle bag, only the best of the best is suitable for her. The only arm candy she’d be seen with is the Balenciaga City. The perfect balance between edgy and glamorous, the City bag features shiny crinkled leather and studded details. Have you ever met a punk that didn’t adore studs? Exactly. The ideal accessory to fit all of Jenny’s schoolbooks inside, the City is true to her style but also practical for her as well. Obviously, she would have the black model, given that you wouldn’t find a single colour inside Jenny’s new wardrobe.
Vanessa Abrams was always that random character that, no offence, everyone hated. Her whole starving artist vibe was cool in the beginning, but you can’t be pretentious and broke at the same time – especially in New York. Though she claimed to dislike it, she was somehow always lurking around the Upper East Side and the elite Manhattan crowd despite working in a Brooklyn coffee shop every day.
In 2019, Vanessa would continue rejecting anything to do with luxury fashion. We assume if she didn’t make it in the film industry, she would have moved to LA, became a vegan and opened up a yoga studio. The ultimate non-conformist, though Vanessa almost always had good intentions it’s no secret that she had one of the worst fashion senses on the show. Her cringy hippie-boho style definitely would have amplified in 2019 - and not the cool, Chloé-esque vibe Serena had going on, we mean like the “dreamcatchers and infinity-sign tattoo” type of hippie-boho. There’s no way Vanessa would ever admit that she’d wear a designer handbag if given the opportunity, but deep down we all know that if someone handed her a YSL fringe bucket bag she would accept it. However, until that happens, Vanessa would definitely carry a tribal-pattern drawstring bag from Johnny Was.
Then there was Georgina Sparks, the true villain of Gossip Girl who only popped up occasionally but wreaked absolute havoc every time she appeared. The definition of a crazy b*tch, when she wasn’t attempting to ruin Blair’s and Serena’s lives she was at bible-camp, running away from the Russian mafia, or sobering up.
Like all villains, Georgia mostly wore black and her style took some influence from Jenny Humphrey’s – except hers was much more chic and much more expensive. Georgina was glam-edgy and if she was around in 2019 we know she’d only have Alexander McQueen, Saint Laurent and Celine by Hedi Slimane in her wardrobe. Georgina was often seen sporting hobos on Gossip Girl, and with the hobo seriously making a comeback lately, Miss Sparks would undoubtedly carry a large Bottega Veneta tote. Spacious enough to carry all her blackmail, her alter-egos and probably weapons (we wouldn’t put it past her), the Veneta is effortlessly stylish without trying too hard. Georgina is also always getting sent away to different locations around the world, so the Veneta is also ideal for jet-setting. An uber-luxe piece that isn’t overtly glamorous, the Veneta is low-key, stylish and practical.