Contains mild spoilers from the first to fourth seasons of Gossip Girl.
As a devoted Gossip Girl viewer and fellow fashion enthusiast, it makes perfect sense that I would love Jenny Humphrey.
Unfortunately, that’s not the case. Jenny is a member of the GG clan who I rarely empathize with and don’t particularly like.
Despite sharing similar ambitions with her at various points in my life, her tendencies to make horrendously wrong decisions paint her as fairly unlikeable, at least in my eyes.
Truthfully, especially in the portion of Season Four I recently got through, Jenny is infuriating, and each one of her horrible decisions makes me even more likely to complain at the screen than the last. However, even if her behavior makes her character seemingly unredeemable to me, I do have immense respect for the outfits she designs and wears throughout the show’s six seasons.
In GG, Jenny (played by actress Taylor Momsen) is portrayed as the epitome of fashion. She is the creative diva who scores interviews with the prestigious Parsons School of Design and works crafting clothing for esteemed designer Eleanor Waldorf. However, being that the show ended 12 years ago, some of her looks have aged poorly.
As the fashion genius we’ve all perceived her to be, her outfits should stand the test of time. Obviously, fashion—like any art—is subjective. Still, at least a portion of her outfits should be still widely considered to be in vogue.
A recurring character for the majority of GG, Jenny plays a predominant part in the series. As a result, she naturally goes through much character development. As her storyline progresses, she goes from a young teen—inexperienced and wanting to be like the wealthy Upper East Side girls—to actually being one of the queen bees she once looked up to. Consequently, as she matures, Jenny’s style evolves from a more innocent look to one displaying her teenage angst.
In the first season of the series, “Little J” is generally seen clothed in bright, lively colors, typically accenting her prep school uniform.
An ideal representation of this period, young Jenny wears a tartan coat, cinched at the waist, paired with an almost matching beret during Season One. Accessorized with brown, laced boots, the outfit only feels like Jenny when factoring in the pumpkin orange tights she wears as bottoms.
On its own, each component of the look suffices, generally staying in warm color territory.
However, when combining all the pieces, the overall look becomes more representative of the cheugy, 2000s styles that Jenny was a product of. While the orange tights are undoubtedly what differentiates this look from any other basic fall one, they are also what make this outfit (debatably) worse.
In her hand, Jenny carries an oversized, multicolored clutch. Truthfully, I cannot tell whether Jenny’s accessory makes the look better or just more convoluted. Its patchwork pattern ties in the safety orange of her biohazard tights but simultaneously ruins the autumn essence of the ensemble.
Overall, the combination of the muted tones and bright shades is representative of Little J. However, the chance of seeing many people wearing this look in 2024 is debatable; it seems to be one that can remain only in GG’s cosmopolitan world of 2007 NYC.
Similar to her orange and brown Season One outfit, Jenny’s yellow springtime look is representative of her youth. Worn in the first season of GG, Jenny is in her era of innocence—prior to getting swept away in her pursuit of popularity.
While Jenny’s colored statements are some of the most adored of the show, seeing the future mean girl in bright tones feels off-putting.
In her buttermilk overcoat with a blue headband holding back her swept hair, Jenny looks almost like a blonde Princess Belle. This look—one of her least wild of the show—would blend in if worn in the 2020s, as it’s pretty simplistic.
Perhaps most true to Jenny’s prep-school queen bee period, she tunes into the academic fashion look with an iconic red-plaid jacket. I say iconic because, when searching up Jenny Humphrey on the internet, seeing this particular screencap is inevitable.
She embodies the aesthetic often associated with GG, coming off as a wealthy prep school girl. Complete with a two-tiered gold headband; Jenny looks like the knockoff Blair Waldorf she was presumably copying.
While it would be annoying to have to wear a school uniform—as the characters in GG do—Jenny helps perpetuate the idea that tartan jackets are chic, not boring.
Even though her early days include plenty of appealing outfits, as she matures, Jenny undergoes a drastic style transformation. Notably, she makes a 180 turn from wearing bright colors to almost all blacks and grays.
Remodeling her preppy look to fit her new style, in Season Two, she wears a red plaid dress. Instead of a gold headband and an air of innocence, she pairs the garment with black bottoms and leather jacket.
While more fitting to her increasingly jaded personality, the look is debatably worse than that of Season One. (Especially because of her roughly-styled, bleached mullet, but that’s a topic for a whole other day).
As Jenny becomes a shell of her Little J self, she undoubtedly develops a more individualistic style. However, during her transition from complaisant girl to teenage rebel, some of her looks fall much flatter than others. Due to this, she looks like she’s simultaneously dressed for Christmas festivities while also maintaining membership in a biker gang.
To keep on the train of some of Jenny’s less brilliant designs, Season Two took her on a stylistic roller coaster. When she runs away from her home, she chooses to pair a lengthy, striped cardigan with gray skinny jeans. While representative of her teenage brooding, I think it would take the top spot on my list of GG’s most repulsive outfits.
Each component of the look—the cardigan, t-shirt, jeans, makeup, etc.—could undoubtedly be paired with different items to be made somewhat fashionable. However, as a whole, she looks disheveled and frightening, like she would want to hurt me if I came near her.
However, almost halfway through Season Two, Jenny reaches a crucial milestone in her fashion career. At age 15, she stages her own fashion show—a feat debatably realistic but, nonetheless, impressive. To her controversial night, she wears a strapless babydoll dress with black, striped detailing. Staying on the bicolored palette, she pairs the off-white lace garment with black tights, boots, and a sweater.
This outfit feels representative of Jenny in her—in my most professional opinion—prime stage of the show. She reaches her peak in the second to third seasons, as she escalates from the status of a normal Brooklyn girl to that of the Upper East Side it girl. What makes this period her finest is that she stays dedicated to pursuing her career in fashion—something that cannot be said for the Jenny of later seasons.
Her outfit at the fashion show is representative of her personal prime. It showcases elements of her signature dark style while not straying too aggressively. As it conveys what Jenny was like in her transition from childhood to adulthood, it is one of my top favorite outfits of hers. (So much so that I may have briefly considered buying the same dress off Poshmark.)
While Jenny’s babydoll dress was beloved by me, it does not compare to one of the casual pieces she wears around her family’s loft in the first season. This brown tartan, a-line dress with pink tulle detailing deserves more recognition. Sadly, it is not crafted for any particular occasion, but the everyday garment is something I would have loved to purchase if it was sold in stores.
Nonetheless, the dress doesn’t really feel like Jenny’s style, even in her Little J period. Regardless, it should be acknowledged and appreciated. With a long cross necklace and various bracelets on her wrists, Jenny looks a bit punk—at least in the more mainstream sense. While making this comparison takes away a slight amount of my love for the outfit, it looks like Olivia Rodrigo could’ve worn it on her SOUR album tour.
After analyzing many looks throughout Jenny’s fashion evolution, she is deserving of her status as a respected stylistic figure. Some of her looks were undoubtedly products of 2000s turmoil, but others do stand the test of time, at least in my opinion.
Even though Jenny had her fair share of looks that fell flat, everyone does—fictional and real people alike. Frankly, her fashion flops may be more representative of her stylishness than anything else. She took risks with what she wore, setting herself apart from all else in the GG universe.
Jenny shows us her talent through the fact that, although not every outfit she wore was award-winning, she was daring enough to experiment with wearing whatever she wanted in the first place—a milestone that few people can truly reach.
