Gossip Girl To Rockstar: 20 Photos Of Taylor Momsen's Evolution

It's fascinating to look back at Jenny Humphrey's fashion sense in the hit TV show Gossip Girl because the character, played by Taylor Momsen, undergoes so much change in terms of attitude and style during the four seasons in which she starred. She was just 14 when she appeared on GG, which debuted in 2007, and her transformation on the show was the most indelible and realistic. She was demure and sweet during her freshman year, then became a rebellious teen starting in the second half of season one, who disobeyed her father by either dating that Dalton boy or by working with Blair's mother, Eleanor Waldorf.

During seasons 1-2, she was not a rebel without a cause. She brought humanity to the preppy girls who oozed wealth and whom she went to school with by telling her father, in a poignant way, that he can't just give her a metro card and expect her to fit in at the school where fashion is king, and where going to pricey restaurants is mandatory.

But the character was resourceful and made her own dresses using a sewing machine. The soapy drama became darker as Humphrey grew up before our eyes, and so did her fashion sense. This is why Little J still sticks out in our memory, even after she left the show during season four. Her attitude reflected her many wardrobe transformations in a way that Blair Waldorf could never do, wearing the same styles episode after episode. So here's to Jenny, whose sartorial transformations come from a real emotion, that of a teen who was trying to tell the world that she was no longer a little girl anymore. So here we offer 20 pics detailing her change in fashion, from innocent prep to a rock star look. Needless to say, both character and actress didn't care about what others thought of her.

20 Jenny Humphrey - Sweet And Petite


Jenny was a sweet freshman wearing a sweet outfit; a yellow jacket and tights and a contrasting bag in red, to transform her boring plaid dress, white shirt and tie uniform into something more colorful and more part of her own style. At this early time in the show, she was greatly struggling with the fact that she could not afford the same things that her classmates could, so she would often rent out clothes or make them herself so she could try and fit in.

This look is chic, classy, and preppy all at once. It's something an Upper East Sider would wear, and something that is more than affordable for anyone else to copy. Especially if the day is cold enough that you have to zip up your jacket, then, who even cares what you're wearing underneath!

19 Prep And Chick


This picture, taken from Season One, shows how Jenny Humphrey can take an otherwise boring uniform and transform it by making it not only cute and classy, but also fun and flirtatious.  You can't really tell that Little J is wearing a uniform,  as her bright red cardigan and matching pumps, as well as her girly polka-dot socks layered over her opaque white tights, makes her look like the preppiest girl in school.

Obviously, the school wasn't that invested in keeping the uniform a certain way, considering the fact that Jenny was not the only one doing as she pleased. Serena often ditched the jacket, and Blair was queen of accessorizing.

18 She Keeps Altering Her Uniform


Jenny may have to wear a uniform as a student at Constance-Billard, but she always puts her own personal style stamp on it. Here you can barely notice her uniform again because of the cropped coat she's wearing that's cinched at the waist to make it look like she's wearing a matching shirt and skirt ensemble. The bag says fun and she copied wearing colorful tights like Blair Waldorf and her minions.

Honestly, these early looks were some of Jenny's best. They weren't over the top, they were stylish and unique, and fit in perfectly with the rest of the cast. Her face was devoid of heavy makeup, which made her look more natural, and she was smiling a lot more too, which definitely adds appeal.

17 The Girly-Girl Look


In season one and season two, Jenny desperately wanted to be part of Blair Waldorf's world that she became one of her minions who had to undergo hazing like breaking into Blair's mother's boutique shop in order to prove her worth. As such, she started wearing headbands like Blair, as well as the aforementioned tights. But while she became a slave to Blair, look at the photo and you'll see someone who looks sweet and demure.

The spring-like patterned dress with pink hues brings out the girly-girl look that Humphrey was known for in the early seasons. It's preppy and fresh at the same time. She looks almost exactly like Blair in the pic above as they share wearing a belt as an accessory and they favor printed dresses over one-colored ones.

16 Rocks Her Uniform While Doing Errands For Blair


It looks like Little J is wearing the same thing with this tweak on her uniform.  But this is realistic. The bag is the same (it's Valentino), and instead of solid-colored tights, she changes it up in an affordable way by wearing patterned tights in fun colors. If she wore the same thing each day, that would be believable because she can't afford to keep up with Blair's ever-revolving wardrobe.

But note that the jacket, which looks like the same one she wore earlier in the season, is slightly different on a second glance. The shearling round collars of the coat is a small but effective change. So even while running errands for Queen B, she still manages to look stylish in her uniform with some added touches of her personality.

15 Jenny's Season 2 Transformation

In season one, Jenny Humphrey had a way of expressing her style by slightly altering her uniform and looking very girly-girl. But in the process of wanting to be part of B's group, she ended up looking a lot like her, as well as her minions. Colorful headbands, colorful tights, long coats, designer goods and other preppy accessories rocked her look but at the same time her style suggested that she was struggling to fit in.

But in Season 2, when her dreams shifted from being B's b*tch to being a serious fashion designer, her style became more unique and organic, as it reflected her wants and needs and her wish to grow up. So her look is more of a cutting edge fashionista with a rock-and-roller edge.

14 Jenny Humphrey's Plaid Phase

It makes sense that Little J turned to plaid in season two because that was a major fashion trend during the filming of GG. She wore plaid in many forms constantly throughout the season because she needs to look like she's in the know, someone who follows runway trends to a T. Most of the plaid comes from plaid dresses, and Humphrey accessorizes them with dark opaque tights and lots of faux jewelry like pearls for a textured look.

Some people think plaid is casual and easy, but when you're going from Brooklyn to the Upper East Side, it's important to make sure that every fashion choice you make is one that is held in high regards. There is no room for error when it comes to fashion on the streets of New York City.

13 Rebellion Has Never Looked So Fashionable

Harper's Bazaar

Eleanor Waldorf, B's mother, has a fashion line and it turns out that Little J has an eye for style and starts working for her. In the process, she skipped school, worked overnight, and made some dresses of her own.

When Waldorf fired Little J, she tried to start a fashion line with a model she met. All that backfired, but the good news is that, while working with Eleanor, she created some of the best dresses, so much so that Eleanor wanted Jenny to make them for her line. The picture above shows a green dress that she made and which Serena is wearing on the runway. It's that dress that made Eleanor swoon--but only after she got mad because Jenny's dress wasn't supposed to be on the runway.

12 In Real Life, The Costume Designers Put Taylor's Character in Designer Outfits


As a potential fashion designer, Jenny Humphrey has to stay in the know about new styles, and she also has to look the part. She needs to look sophisticated and fashion-forward. Of course, Jenny doesn't have the wardrobe of a fashion designer. Even in school she had to wear clothes that she made herself on her sewing machine. But in real life, everything Jenny wears is made by the top designers, and her wardrobe for a day can cost in the thousands.

In real life Taylor Momsen loves Dolce & Gabbana, as well as Marc by Marc Jacobs. As such, when she has to wear sweaters, the costume designers look for something from there. Thus, Jenny wore a Marc Jacobs cashmere blend zipper cardigan in one episode and a Marc by Marc Jacobs sequinned merino wool cardigan in another episode, among many other things.

That yellow belted trench coat that Jenny wore a lot in season one is not from Forever 21. It's by celebrated designer Michael Kors. And her purple studded bag she had is by Valentino was such a success in real life that retailers ran out of them. That reddish-pink necklace that Jenny sports in season 1 is a Tarina Tarantino lucite necklace. She also wore a lot of outfits from D&G, mostly skirts, and two stand out, a pink bustier dress and a  plaid shirt dress when she was in her plaid phase.

11  Jenny Humphrey Gets Darker


Before she started wearing even shorter skirts and sported a goth look,  Jenny Humphrey was in a transitional stage. She moved away from bright colors and plaids to wearing monochromatic, such as her all-black outfits.

Black is sexy, but without textures and accessories and a splash of color, it can be boring and repetitive. That's why she also adds grey to her black outfits. It's a sign of a burgeoning sophistication and maturity, and of growing up too fast. The two colors signify change, and Jenny starts wearing leather, such as a vintage leather jacket. She also wears jackets in black and grey.

10 Pops Of Color To Up Her Black-And-Grey Wardrobe


In Season 2, Jenny is still struggling to find her identity. First, she had her plaid phase and then she had her black-and-grey look. Squeezed in the middle is the girl we know, the sweet kid who gets swept up in Blair's world before finding and expressing herself by working as a seamstress for Blair's mother.

As a freshman, Jennie was all about adding pops of color to her wardrobe, and her favorites were yellow and purple. This semester, Jenny likes hot pink and neon magenta, and she successfully finds a way to add a pop of color to her grey and black outfits in the form of a scarf or a skirt. Or you can do it the Jenny way by wearing a pink tulle skirt under your regular skirt.

9 The New Jennie Humphrey - Season 2


From the start of the series, Jenny wore more hats than headbands, which gave her a signature style. This season, she also accessorizes by wearing a knit hat, a trendy bowler or a beanie. And instead of bright bags as an accessory, Jennie turned to wearing jewelry.

Lots of jewelry that she piles on in layers on her neck as well as lots of bracelets on her arms.  She doesn't care what matches. She'll wear silver and gold, as well as pearls and black beads. These looks border on boho chic, but most of all they look like a move away from the sweet Jenny we knew.  To be more accurate these accessories foreshadow the rock-and-roll look, and as the episodes pass and go, we'll see her coming into her own.

8 Jenny Humphrey Rocks It In A New Haircut

This is one of biggest change that Jenny did to alter her look. It's a very drastic move, as Jenny cut a lot of her hair so that it is shoulder length. The result is that the hair is choppy in the back and in the front she has heavy bangs. It's not a look for everyone, but Jenny's not looking to please now. She curls her hair in the back in soft curls and the platinum blonde locks seem like a homage to Debbie Harry.

This was quite a shock to the viewers, when her drastic changed occurred from one season to another. There was nothing wrong with it before, as she manages to make the look work for her, but viewers were naturally quite confused about the direction that Jenny was taking in the show, especially considering the fact that not a lot of people knew that she would be moving on to music.

7 The Transformation Of Jenny Humphrey Is Complete

Her makeup is all black, with caked on black eyeliner and shadow. As her older brother Dan rightly said, she looked like a raccoon. But Jenny was going for the dark rock style look, all-punked out and far away from the image she had during her freshman year. She even pairs her wardrobe by wearing torn fishnet stockings.

6 Jenny Lets Her Hair Down For A More Punk Rock Look

Jennie is forever changing her look, although her style remains a rock-and-roller. Now, after coloring her hair platinum blonde, she grew her hair out and wore extensions and suddenly you could describe her as an adult. With this long hair look, Jennie moves to the Upper East Side with her family and Serena's family.

It's during this time that Jenny wants to be Queen of Constance and with Blair's blessing, she starts her reign and her hemlines get shorter and shorter with each episode. Because she's leggy, she never wears pants. Who wouldn't want to if your legs are thin and lithe?

5 Fishnets Are Now De Rigueur Thanks To Jenny

In her new phase during Season 3, Jennie starts pairing her black and grey outfits with fishnets, trading in the coloured preppy leggings that she used to wear to become like Blair.

It seems all her outfits are accessorized by fishnets, and the Queen teen is looking all grown up. She's still showing off her legs, so she tops the fishnet for super-short dresses and knee-high boots. Add in her now trademark leather jacket, which is not shown above but is in the show, she has brought the look up with her on stage. She's honestly, one of the few people who could pull off a look like this so well. A lot of the time it might look trashy, but she has brought it up to a level that is specific to her, almost attributing this new grunge look to her.

4 How To Accessorize Like Jenny Humphrey


Jennie likes a lot of textures, so her apparel and accessories have a lot of silver spikes and gold studs. Anything metallic is what she likes the best. And that's seen in her boots and bags. Nearly every episode Jenny wore high-heeled ankle boots in black, although she does have some in grey, her two new favorite colors in Season 2 and 3. Of course her boots have to have studs, and she also wears those with zippers. But what always is constant is that the boots have to have at least a 4-inch heel, making her long legs even longer.

For bags, she used to wear purple and red ones such as the red number above. But in Season 3, when she went all black all day all long, she carried black leather bags, but only if they were of her interest, such as bags with metal accents, just like in her boots. Jenny also goes for bags with silver spikes and gold studs. These accessories can be seen not just in her boots, but in her bracelets and sweaters. One last thing: if you want to be Jenny circa 2009, invest in Ray Ban Aviator Sunglasses, which are the trademark glasses that she almost always wears.

3 The Real Reason For Jenny's Change


It was during Season 3 that Taylor Momsen started a rock band called The Pretty Reckless. Her transformation on GG, including the hair extensions and black eye makeup, was due to her starring in a real-life rock band. As Momsen's real band started to rehearse and play, the producers behind Gossip Girl were obligated to change Jenny's wardrobe to reflect Momsen's style change and her life and look outside the show. As producer Joshua Safran told Vulture:

"It was hard at a certain point to write for the old Jenny; we had to write for the new Taylor. . . Taylor wanted her hair a certain way because she was in the band and that was who she was, so we couldn’t dye Taylor’s hair to be Jenny every day, especially when she had events where she had to be Taylor for the weekend. So Jenny had to change."

2 The Face Of Madonna's Clothing Line

In 2010, when Momsen was only 16, she became the face of Madonna and her daughter Lourde's fashion line, "Material Girl." She was their celebrity muse and had the perfect look for Madonna's collection. "Material Girl" was sold exclusively at Macy's, the department store.  The clothes and accessories are inspired by Eighties rock, which just happens to be the time Madonna emerged as one of the most popular pop singers in the world.

This is an easy fit for the rockstar, considering her fashion taste is exactly in line with Madonna as it seems. The photo above is a clear statement of that, lined up next to Madonna and her daughter, all three of them in black and showcasing just how good she manages to look in similar fashion.

1 Usher In The New Momsen Whose Photos In This Magazine Are Too Racy For Us To Show

Two months after she appeared on the cover of French magazine Rock One, Momsen appeared on the March 2002 cover of UK's FHM. Only 18, the photos inside the magazine are so racy that they are too scandalous to show you.

In one photo she's on all fours atop a kitchen stove posing with clothes that barely make an outfit, with a pout on her face. In another she's posing behind a  female model and using her arms and hands to cover the model's cleavage. Finally, in the strangest shot, Momsen appears is making the effort to cover her body up with her own arms and legs, covering herself in an expert way that still shows her off. Besides those boots, she's only wearing her trademark fishnets. Now that's a true transformation!

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Gossip Girl To Rockstar: 20 Photos Of Taylor Momsen's Evolution