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Starrin n Stylin: Styling the Gossip Girl Characters in 2021

Updated: Aug 3, 2022

The original series of Gossip Girl has finally returned to the UK, now available on BBC iPlayer. One of the drama’s biggest attractions were the characters’ clothes; all took a different spin on the preppy Upper East Sider look. Whilst Serena van der Woodsen was more rebellious and revealing, Blair Waldorf was a twist on vintage styles. Jenny Humphrey, however, blossomed from Blair’s minion into her own rock-chic style. In this, we look at how these three characters may dress if the show was set in 2021.

Blair Waldorf

Blair Waldorf’s style was always 60s and Audrey Hepburn-inspired, however, for a contemporary version, this would become more refined. In the era of Gossip Girl, fashion was more over the top, with chunky jewellery and layered fabrics, whereas contemporary silhouettes are more streamlined. This change would in fact hark back to the 60s fashion Blair loved so much.

There would be an array of two piece sets. In recent years, these have come back into fashion, arguably inspired by the original Chanel two piece. Blair would wear these for a multitude of occasions; Burberry Spring ’20 for brunches, [.] Two pieces, since they already coordinate, create sophistication by default. If Gossip Girl was set in 2021, Blair would use this automatic elegance to her advantage.

Serena van der Woodsen

Although Serena van der Woodsen’s style in the series was labelled boho chic, her carefree energy would be reflected as 'model off duty.' Boho chic was the style of cool girls in the late 00s, however now, it is the effortless fashion of supermodels. Serena was always seen as the series’ bombshell, and often charmed her way out of trouble. If Gossip Girl was set in 2021, Serena would most likely be a model, similar to Julien Calloway in the reboot. Therefore, Serena’s style would exude fashionable nonchalance.

The model off duty style would be reflected in simpler outfits like jeans and t-shirts, an ode to 90s supermodels. They didn’t have to wear something to attract admirers, they already had ‘it.’ This would, however, be mixed with the nonchalant experimentation of contemporary models; think Bella Hadid, especially with the cutout tops she has worn recently. Serena did like to take risks with her outfits in the original show, so experimental items alongside more casual pieces would be a great revival of this. An example of this would be the most recent Jacquemus collections, where an elegant silhouette has been updated using unconventional cuts.

For evening wear looks, an important part of the original Gossip Girl, 90s Versace would be a must for Serena. She loves attention-grabbing fabrics, and Versace’s collections in the 90s were full of sequins and sparkle — not to mention, they essentially birthed the concept of ‘the supermodel.’ Metallic fabrics are trending now as well, using bright colours instead of the normal gold and silver tones. I think Serena would take full advantage of this, reflecting her confident personality.

Jenny Humphrey

Jenny Humphrey’s style evolved into rock-inspired, high fashion excellence. Her style became an expression of her rebellion against the normal Upper East Side It Girl.

For an updated version, the love of garters would be paired with lingerie, like corsets. She would be inspired by Dolce and Gabbana, mixing lingerie with comfort. Although she was glamorous, her outfits were sometimes more relaxed. The use of lingerie would be a great presentation of her indifference; I would emphasise her grunge and Gothic tendencies to contrast her against Blair and Serena. Jenny made most of her outfits and wanted to be a fashion designer, so I think she would be aware of the messages of brands. She may be inspired by the Vivienne Westwood corsets, especially because of the brands’ message of self-expression and equality.

As an aspiring fashion designer, Jenny could be inspired by more experimental designers like Alexander McQueen and Jean Paul Gaultier, and create looks similar to these. This would also create a visual difference between herself and the two It Girls she wrestled power off of as the series progressed.

However, reflecting her days as Blair’s minion, Jenny would wear two piece sets, only with decals like the Chanel chains (or something similar) for an edgier look. This would show her character progression throughout the show, whilst emphasising Blair’s power.

Edited by Lucy Eaton


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