A Look At Our Favorite Gossip Girl Fashion Looks

Gossip Girl Reboot Fashion

Spotted on the Upper East Side: our very first peeks at the upcoming Gossip Girl reboot by HBO Max. While some New York treasures bit the dust for good, like Nicolas Ghesquière-era Balenciaga and apple cobbler cupcakes from Crumbs Bake Shop, our jaded little hearts are aflutter at the possibility of seeing S, B, V and Little J painting the town Louboutin red again.

Also, how much longer until we can start referencing Gossip Girl in film studies seminar at Tisch?

K and M are still waxing eloquence about their favorite looks (or in 2020 speak, lewks) of the original 2007 series. Not everything was peachy behind nostalgia’s rose-tinted Tom Ford aviators, but we’ll always remember the fashion fondly. After all, taste is subjective, but B’s Harry Winston diamond ring is forever.

Best Gossip Girl Style Moments

Jenny Humphrey Fashion Looks

Gossip Girl Jenny Black Fashion Style

M: Dark monochromatics with thick tights and booties are a true New York fall staple. The layering of grays and blacks sends my early aught’s teenage emo heart into a tizzy.

Gossip Girl Jenny Best Fashion Dress

K: Little J is known for her rocker chick fishnet look. But she proved all her jealous haters wrong with this elegant and sophisticated black dress. Don’t be fooled though, she added an edgy accessory, a Patricia Field half leather gloves, staying true to her badass fashion style. 

Gossip Girl Jenny Fashion Shoes

Bella Belle Jenny Fashion Shoes

Photo: Laura Gordon. Shoes: Bridget, Rita. 

Jenny loves her studded black boots or velvet blue boots. But Little J also loves pumps and heels that marries elegance with edgy. Bella Belle Rita is a sweet (tiny bows) and edgy (sexy caged look) bootie, perfect for Little J. 

Another option that little fashionista Jenny would go for is Bridget, a classic stiletto with feathery pleated tulle with black polka dots embroidery. Even Queen B will take note of the shoe choice. See more Jenny-approved black heels that are full of beautiful handcrafted details (which Jenny would appreciate - from her humble beginnings of sewing her own outfits). 

Vanessa Abrams Fashion Looks

Gossip Girl Vanessa Fashion

M: Colorful prints and layered chunky jewelry instantly connote “unorthodox Brooklyn artist” and captures Vanessa’s laid back demeanor in a snap.

Gossip Girl Vanessa Fashion Best

K: I am obsessed with the way V used this blue layered necklace with gold hooped earrings and beaded bracelet to complement her color block look. This is the way to do color blocking and jewelry right. 

Unlike her wealthy Upper East Side peers, Vanessa had a more humble background and her fashion style was a reflection of that. She might not have Gucci or Prada pieces, but she does have an acute sense of trifting and using accessories such as jewelry and fun shoes to show her fun and laid back personality. 

Gossip Girl Vanessa Fashion Sandals

Gossip Girl Vanessa Fashion Boots

Photo: Tamara Gruner & Laura Gordon. Shoes: Luna, Nikki. 

For the summer months in Brooklyn reading at cafes, she would wear Luna gold jeweled flats. During the colder months or for her soiree at the Upper East side, she would wear Nikki that adds sophisticated and an elegant flair to her more boho chic style. These comfortable shoes are perfect for Vanessa who prioritizes comfort over style. But don’t be fooled, just because they are comfortable it doesn’t mean they are any less stunning. 

Blair Waldorf Fashion Looks

Gossip Girl Fashion Look

M: Headbands are her most celebrated accessory, but Blair’s cape collection is criminally underappreciated. Don’t we all wish we could show up to Thanksgiving with this elegant all-brown ensemble?

Gossip Girl Fashion Look Best

K: There is a lot going on with this outfit, from the giant fruit patterns to the array of colors, and yet, it totally works! The beret is the perfect finishing touch for when Queen B wants to step away from her classic headbands. 

Queen B is the queen of mixing patterns and bright colors that you would never think would work together, easily making her one of the most fashionable television characters of all-time. She is also known for wearing patterned tights and reviving the classic headband accessory to make it the hottest fashionable accessory trend in the 20th century. 

Gossip Girl Fashion Look Pumps

Gossip Girl Fashion Look Heels

Photo: Laura Gordon. Shoes: Dorothy, Gabrielle. 

Her shoe choice consists of pumps and would always choose a classic pump over a bootie or flats. Pumps like Dorothy that have a couture-like beaded bow, and Gabrielle with embellished pearls (a jewel that Blair loves), are very much up in her shoe alley. You’ll be sure to find any of these classic pumps in her posh and preppy closet. 

Serena van der Woodsen Fashion Looks

Gossip Girl Serena Fashion Looks

M: I attribute this pivotal TV moment to why I go to Stuart Weitzman and greedily whisper to the boots, “I don’t want anyone else. I want you.”

Gossip Girl Serena Fashion Looks Best

K: A textbook Serena look - pairing something glamorous with something super casual, all for a shopping trip in Paris. Serena perfectly wore a Georges Chakra glittery cage dress with a fedora, Oxford shoes, mannish blazer and a leopard print bag. On an average person, this fashion combo would be arrested by the fashion police but on S, it’s one of her most iconic looks on the hit TV show. 

Serena’s fashion style is more relaxed with a hint of boho chic. She loves sequins, tailored shorts, ballet pumps and vintage pieces. It almost felt like anything Serena puts on, she looks amazing. While her bestie Blair was the Upper East Side queen of prep and posh, Serena is the queen of ‘I woke up like this’ and looks fab every single time.

Gossip Girl Serena Fashion Looks Flats

Gossip Girl Serena Fashion Looks Heels

Photo: Kayla Barker, Morgan Franklin Creative. Shoes: Pippa, Elsa. 

As a lover of sequins, Serena would fall head over heels for Elsa in nude which has hand-beaded crystals, sequins and beads in a perfectly crafted nude pump. As a lover of comfortable flats with boho elements, she’ll love Pippa nude flats that have multi-colored floral beading. Serena would totally wear these fashionable shoes for her Paris shopping trip, a fun evening out with the girls or to grab a cup of coffee. 

The Gossip Girl reboot may motivate us to stop relying on our roommate’s boyfriend’s brother’s Netflix, and finally pay for our own streaming service. Like springtime in Central Park, new beginnings are afoot. Will Constance Billiard’s incoming class turn over a new leaf, or is history prone to repeating itself? No matter the changes, we’ll always have New York.

You know you love me.

XOXO,
Bella Belle

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