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18 Images Of Taylor Momsen’s Evolution From Whoville To Gossip Girl

It's no secret that Taylor Momsen has gone through a total transformation during her time in Hollywood. When audiences first met the blonde cutie, she was a child star being brought to auditions by her mother. She booked several commercials and got her big break when she snagged the role of Cindy Lou Who in the live action version of How The Grinch Stole Christmas. She went on to appear in a few other projects after that, and then entered the spotlight once more when she got the role of Jenny Humphrey in Gossip Girl. While other characters like Blair and Serena maintained their style throughout the show, Jenny's style changed drastically from season to season — and we have to wonder if some of that was designed to reflect the changes that Taylor's own style was going through.

When she hit her teenage years, Momsen was no longer content to play the cheery blonde starlet. She started dressing in a more edgy, punk, almost gothic way, adding layer upon layer of eyeliner, and basically just transforming in front of the public's eyes. She began bringing up controversial topics in interviews, and even entered the rock world as the lead singer of The Pretty Reckless.

Here are 20 images that highlight Taylor Momsen's insane transformation over the years.

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18 3 Year Old Taylor In A Shake And Bake Commercial

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While it's certainly not easy for any child to be in the entertainment industry at a young age, Taylor Momsen in particular has been very outspoken about the fact that she never wanted to be an actress — not initially, at least. Her mother took her to various opportunities for child modelling and commercial work, and Taylor ended up booking gigs because, well, she was adorable! We're not exactly sure why she continued acting once she was a teenager, at which point she could have easily hung up her actress hat, but hey — you never know. Perhaps all her years on Gossip Girl added enough to her bank account that she can now just focus on music and not really have to worry about making money.

17 Playing Cindy Lou Who

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If you looked at Taylor Momsen today, you would absolutely never guess that she was the same actress who played the adorable Cindy Lou Who in the live action version of How The Grinch Stole Christmas. And no, it isn't just because Cindy Lou had some seriously over the top hairstyles. Now, it's not uncommon for someone's face to change a bit as they age and lose some baby fat, but Taylor's face has changed dramatically — you would never guess that it's the same person! We wonder if any of her former cast mates on this movie see the path she's taken and wonder if they should chat with her a bit about the challenges and pressures of Hollywood — it definitely seems like she's desperate to court controversy at every opportunity.

16 At The Premiere Of How The Grinch Stole Christmas

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It's one thing to attend a premiere when you're one of the supporting characters — it's an entirely different experience when you're arguably the star of the film. For the live action version of How The Grinch Stole Christmas, there were two huge central characters — Jim Carrey's Grinch, and Taylor Momsen's Cindy Lou Who. So, Momsen definitely had to do her fair share of press to promote the film. And we have to admit, we have a lot of questions about when child stars do press. First of all, do they get a stylist like adult actresses do, or are they just on their own when it comes to finding red carpet outfits? We're not sure who came up with this patterned dress and yellow jacket look, but hey — if she feels confident in it, it's the perfect thing to wear to her premiere.

15 Adding To Her List of Credits With Spy Kids 2

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How The Grinch Stole Christmas may have been Taylor Momsen's first major film role, but that doesn't mean it was her only film role. In fact, she's been working steadily from almost before she could talk. She added to her list of family-friendly film credits with Spy Kids 2, the action packed sequel to the original Spy Kids movie. And we have to admit, it seems like an entirely different actress. Never in a million years could we imagine Taylor rocking sweet brown curls and a cardigan in any role today — even if the costume department demanded it of her character, she'd probably add a few rips into the cardigan or add something more scandalous to make it her style. It just goes to show how much people change as they grow up.

14 A Tween Taylor Experimenting With Being A Brunette

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Nowadays, Taylor Momsen is most associated with her platinum blonde hair. Though she's worn different levels of eye make-up and had everything from a bob to long, long extensions, she's been super blonde for years now. However, back when she was just a tween starlet trying to transition from roles in family films to roles in different types of projects, she tried out brunette locks for a while. We have to admit — while she looks stunning regardless of her hair colour, we kind of love her platinum locks far more than the brunette hair. Her entire personality is about pushing the envelope, so the edgier shade just seems to fit her personality a lot better. However, who knows — maybe one day she'll get tired of the blonde and decide to go dark.

13 Looking Like Every Other Blonde Teen Starlet

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We're not sure if her team of stylists was just firmer with her back when she was a starlet on the rise, or if she just hadn't yet found out what her preferred style was, but there's no doubt that she looks drastically different in this shot than she did just a few years later. In this picture, she could be any blonde starlet who was poised to make her big break in Hollywood — she looks fresh and young and gorgeous, and we can understand how the team at Gossip Girl would want to cast her as one of the younger cast members. She definitely looks like she could become a huge A-List star and transition from teen flicks to becoming a leading lady in rom coms — Reese Witherspoon, look out! That's not the path she ended up taking, but hey — it's fun to get a peek back at younger Taylor.

12 Looking Sweet As Pie In Gossip Girl Season 1

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Given how her style changed in the later seasons, it's a little crazy to see how fresh-faced and youthful Jenny looked in earlier seasons of the show. We can't picture Taylor Momsen wearing a sassy blue headband, or such a bright, sunny shade of yellow, but it definitely worked on Jenny. It just goes to show how big an impact wardrobe has on a character — in the first season or two of the show, Jenny was always wearing bright, almost juvenile clothing, and definitely seemed like a younger sister. As the show progressed, her style evolved, as did her attitude, and she definitely fit in more with the elite Upper East Side schoolgirls like Blair and Serena. We have to give the costume department on this show major props — there were some iconic looks.

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11 Starting To Rock A Slightly Edgier Style

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There are plenty of starlets who have never, ever gone short with their hair — they've worn their hair long since they were an aspiring actress, and they're not going to chop it off for anything. However, Taylor Momsen doesn't have that issue — while she's known for her long locks now, and she definitely had long hair when she was a child star, she also experimented with shorter locks during her teenage years. Her shorter hair period coincides with the period when she began experimenting with an edgier, more punk rock style — and she even got bangs! As you can tell by her more subtle smoky eye, she wasn't quite in her total rock chick phase, but she's definitely stepping away from the typical starlet look in favour of something with a bit more edge.

10 Starting To Commit To The Punk Style Vibe

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We have to admit, we're kind of curious whether the costume department decided to take Taylor Momsen's character towards an edgier style, or whether Taylor's own style influenced the decision. After all, if your star is being difficult and refusing to wear frilly, pastel clothing, it might just be easier to switch up the character's style — and in Jenny's case, it definitely fit. While Blair Waldorf certainly had a defined sense of style that would make a drastic wardrobe change a bit strange, Jenny always seemed like she was still trying to figure out exactly who she was, which means the huge overhaul of her wardrobe kind of seemed appropriate. She may not have the crazy eye make-up here that she favoured for a few years in her personal life, but we can totally see her wearing this outfit off set as well.

9 Definitely Darker, But Still Not In Raccoon Eye Territory

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You can definitely see a huge difference between the kind of clothing Taylor Momsen's character Jenny wore on the show during her punk phase, and the kind of clothing Taylor Momsen wore in real life. You see, in real life, Momsen wasn't really worried about being chic — she seemed more concerned with picking clothing that was as shocking as possible, and revealed as much of her body as possible. On the show, the wardrobe team wanted her to be edgy, but still chic — hence the slouchy heeled boots, the fishnet stockings, and the artfully layered tops. The look is a kind of hybrid sultry grunge vibe that we're totally digging — and we have to admit, the darker lip and slight smoky eye is definitely more appealing than the super heavy liner she wore in later years.

8 Starting To Channel Her Inner Rocker

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Taylor began working with her band The Pretty Reckless at the same time she was on the show, which we have to guess had a huge impact on the character Jenny ended up becoming. After all, if one of your main cast members becomes a legit real life rock star, why not incorporate that edge into her character whenever possible? This shot shows Momsen during a performance, and her outfit is definitely peak punk rock Taylor. From the leather jacket to the braids to the slight smoky eye to the graphic tee and necklace with dark symbolism, it's definitely a look that screams 'I don't want to be considered a teen starlet or associated with any kind of teen television.' We do sometimes wonder why she didn't just up and quit far sooner.

7 Stocking Up On Eyeliner For The Red Carpet

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Okay, now we're deep into Taylor's punk rock phase. First of all, just check out the major smoky eye — she's definitely not afraid to pile on the black liner, and the result is a pretty arresting look. Then, the long hair — waist-length, slightly curled, and hanging down in curtains. Even the accessories, from the choker to the strappy details on her leather jacket, scream that she's trying to look tough. Hey, if this style is what truly spoke to her, we say go for it — however, we can't help but wonder if a lot of her style decisions during this period in her life were made solely based on what would be the most shocking on the red carpet. After all, there's a big difference between refusing to wear a pastel dress on the red carpet and going full on gothic with your look.

6 Adding Crazy Long Extensions To Amp Up Her Style

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It's no secret that countless actresses in Hollywood have extensions, either because they need longer hair for a role, they simply want longer hair, their actual hair is damaged from all the styling on set, or they just want a bit more volume and fullness added to their thin locks. However, usually, you can't tell when an actress has extensions — it just looks like she has fantastic hair. In Momsen's case, she didn't seem particularly worried about her extensions being believable — she just wanted a particular look, with long, blonde locks. The result is pretty insane. We kind of wish she would have either taken better care of her extensions or perhaps added more to give her hair some volume — this look is limp and definitely not super flattering for her gorgeous face.

5 Adding More And More Liner, And Darker Lip Colours

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There was a time back in her teens where Taylor Momsen seemed to add more eyeliner every single week — and this is definitely peak raccoon eyes. Look, there's absolutely nothing wrong with preferring a smoky eye over a more neutral look — sometimes, it can be incredibly fun to play with make-up. However, we have to wonder if this sheer amount of black liner and shadow surrounding her eyes ended up hurting — it seems like it could even jeopardize your sight. Plus, we don't even want to imagine how long it took to fully wash this off. Although, who knows — perhaps she just let her liner and shadow hang out on her face and get more smudged by the day. This is definitely the kind of look that gets stronger the messier it becomes.

4 Going Way Overboard With The Black Liner and Shadow

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We have to admit  — we're kind of glad that Taylor Momsen eventually ended up toning down her look a little bit, because during this period in her life, she definitely went a bit overboard with the liner. We totally get what she was trying to achieve, but her smoky eyes ended up totally overtaking her face, and not in a good way. She's so gorgeous, and can pull off the edgier style so well, that this just seemed like overkill. Particularly if she's smiling and not wearing darker lipstick, it looks like she made a huge make-up mistake and didn't even notice before she left the house. Seriously — all we want to do is come at her with a few make-up wipes and clear off some of the excess here, because it's just way, way too much.

3 Experimenting With Different Gothic Looks

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As you can see, the all black eye make-up wasn't the only look that Taylor Momsen experimented with during her gothic phase. She also tried out her fair shade of dark, vampy lip colours, and even tried switching up her black shadow with other deep shades, such as burgundy. This look definitely isn't for everyone, but we have to admit, she looks like a sultry vampire ready to kick some butt and take names. Even though it's still a strong look, it's much less severe than the all black shadow, and a little more chic. We wouldn't be mad if she decided to revisit this kind of look every now and then on the red carpet — it would certainly set her apart from the crowd, in a good way this time!

2 Performing In 2015, Letting Her Style Get A Bit More Casual And Less Provocative

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Right when she started performing with The Pretty Reckless, Taylor Momsen had a very distinct on-stage style. She had the long, blonde hair, the smoky eye make-up, and generally wore super goth-inspired things, from crazy short, skin-tight lacy dresses to looser clothing that also showed a lot of skin. She rocked a lot of leather, torn items, and basically tried to look as grungey as possible on stage. While it was certainly a distinct look, we kind of dig the more mature take on gothic style that she rocked in the later years. You can see a hint of a lacy bra peeking out here, and the cross pattern on her t-shirt is definitely typical of her style, the overall look is a lot less designed to shock and just more an expression of her on stage persona.

1 A More Modern Take On Her Goth Style

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Okay, this photo is basically proof of what a huge style transformation Taylor Momsen has gone through over the years. First of all, she's no longer wearing the stringy, limp blonde extensions — while she's kept her edgy platinum blonde locks, her hair looks way more healthy overall. Second, she's switched up her make-up game, and her overall look is a lot more chic — the smoky eye remains, but it's a far more toned down version, and paired with a neutral lip. We have to admit, we kind of love this new Taylor — it has all the edgy sass of her previous look, but it's far more flattering. It just goes to prove that sometimes, less is more — and just think of how much money she's saving on black liner and black eyeshadow!

References: starcasm.net, huffingtonpost.com, popsugar.com, youtube.com, justjared.com

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